Kevin “KD” Dorsey is the VP of sales at PatientPop and runs a Patreon group, Inside Sales Excellence, with the tag line, “Live Better, Sell Better.” He also hosts his own podcast, “Live Better, Sell Better.” He talks about bringing the person in the salesperson. He shares best practices within the sales profession and personal development, leading to numerous recognitions. After this episode, you will see why. KD goes in-depth on his framework of living a better life, tactical stories on prospecting and closing, and sharing his Go-To-Market Strategy framework.
In this episode, Mike talks about his Go-To-Market sales strategy and tactics to execute his plan. This conversation covers recruiting to the sales process. Mike Hook is the head of sales at ChildcareCRM; he shares how he approaches Go-To-Market strategy and then details how to accomplish it. We dig into the bottoms-up model, recruiting, coaching reps, and so much more. As a 2020 LinkedIn Sales Star, you will see why he provides so much value on the platform.
Let us know what was your favorite quote or lesson from this episode? Please let us know in the comments!
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Show outline, stuff mention, and transcript
Click to see the full details
Lessons from being a door to door sales rep [0:00]
How do you think about GTM Strategy [5:38]
How to hit the number and breaking different channels [8:38]
Tactical advice on sales [11:30]
Coaching reps [14:10]
Recruiting reps, qualities, and questions to ask [19:10]
Change in the landscape, product-led growth, changes in buyers [25:01]
Framework on making questions [28:10]
Humanizing Sales [33:41]
Professional failure and lessons learned [38:51]
Habits/Process that has helped [42:50]
Last message [48:01]
In today’s episode of the Go To Market Podcast, we have Gabrielle “GB” Blackwell. I cover a capability matrix, use it to build any segment/organization, and move up in the matrix—also, thoughts on remote work and coaching. We also get into GB’s process of finding mentors and advice on careers/life. This was a fun conversation and with tons of value of information.
Leave a comment on your favorite part or quote in the comments below
Click to see show notes, stuff mentioned and transcript
Professional Journey [:55]
Expanding on being a CEO [2:00]
Building SDR Organizations [3:51]
Going from Adhoc to capability [5:30]
Describing what data to look at [10:00]
Thoughts on onboarding and managing remotely [11:46]
Mental framework on coaching [14:58]
Building Trust [17:01]
The time when something didn’t work [20:01]
Evaluating Operations Excellence [24:42]
Breaking down ideas [28:02]
Lessons learned from family [34:30]
Mentors and resources [40:02]
Personal development [43:02]
Advice on career [46:00]
Last message [49:50]
For our episode, we have Elias Rubel, the Founder Partner/CEO of MatterMade. Where they help the most promising venture-backed B2B companies hit their audacious revenue goals faster. Teams at Dropbox, Calm, and Sticky.io have leveraged Matter Made. Clients are back by Sequoia Capital, True Ventures, NEA, Redpoint, and just about every other big name in the valley. Before MatterMade Elias is a 2x founder. In this episode, Elias dives into the cutting edge of marketing, what decision doing marketing, what are companies commonly doing wrong, and how to fix it. This episode is for anyone interested in accelerating their growth.
Please tell us your favorite part or quote in the comments below.
Show notes, outline and transcript
Click show more to find details on the show and the transcript.
Elias introduction [:41]
How does Elias apply his Charlton background to B2B strategy [1:30]
Exciting things in B2B marketing [2:30]
Decision-making marketing [4:10]
Why is authentic marketing more prevalent [9:50]
Elias projections of 2nd and 3rd order effects of the pandemic [11:35]
What patterns of what companies are doing wrong [13:40]
How to validate marketing messaging is working [15:00]
Communication cadence with different parts of the Go-To Marketing team[17:10]
How rev ops is an essential part of Go To Market [19:44]
How to start aligning marketing and sales and what metrics matter [22:00]
How Elias developed different mental frameworks [24:00]
How to think about recruitment? [27:20]
What habits and process help Elias in his day to day [30:10]
Last Message for listener [38:10]
Walter Pape: let’s do this, man. Everyone, watching and listening, will give some context of who you are, and you will find your roles and responsibilities.
Elias Rubel: Yeah, for sure. Well,
Elias Rubel: For background. My name is Elias ruble, and the founding partner at Matter Made is a B2B growth marketing firm. We work with companies like Dropbox and calm. Many other venture-backed high growth startups and scaling companies help them scale revenue on the business’s marketing side. So that’s, that’s what I’m up to now. My background, though, ranges. I started a venture-backed software company that was acquired in 2014. We did contract lifecycle management software, not a space I expected, my first company to be in. But, uh, you know, hey, I picked a category that was unsexy and went for it. I’ve also, you know, scaled an e-commerce business or not to private equity, and so I’ve got a bunch of really my backgrounds weird, man. It’s all over the place.
Walter Pape: Yeah, no, that’s awesome. And I think that’s one of the things that I, you know, I guess so appreciated having a very unique and weird background, you know, within that. How do you now apply your past experiences to help companies with their go-to-market strategies and growth plans?
Elias Rubel: Yeah, that’s a great question. I mean that’s really everything right is like pattern matching and kind of having those experiences to call on I think that initially even before matter made you know I’ve always been big at just like having a lot of irons in the fire and testing different things and then waiting to get some form of signal. Whether that’s at a macro level with companies like multiple companies or, you know, more micro-level with campaigns and testing kind of quick iteration on that front, that said, nowadays, what’s fantastic is we’re working with and helping scale anywhere from five to 10 high growth B2B startups, a year. And so, you know, whereas your average revenue operator or marketing leader is going to be with the same company for. Call it three years, something like that, you know, they get deep on that one specific problem space. But then when they move on there. They’re learning all over again. Our ability to see patterns in the industry and test all sorts of, you know, the tip of the spear in B2B marketing and growth and Test and learn from that. Then we get to deploy that for our new clients. So it’s cool to take that pattern matching, learn quickly, and then see results from it.
Walter Pape: Well, what. So what are some of those pattern matching? I mean what, what is it that you’re seeing. I mean, what would you say kind of high level are you sort of like recognizer right now is some exciting things
Elias Rubel: Sure, yeah. I mean, I think the one that’s in front of everyone. Right now, and everyone’s trying to figure out how to react to it, you know, we’ve been in this. We’ve been in this shift back towards authentic community building and social selling. I mean, those things never really went away, but for a while. There it was a little bit more mechanical, a little bit more, you know, case studies and white papers and downloaded content gated content. Now we’re moving to this place of, you know, authenticity, sharing freely, not getting content. I mean, it’s that statement that we keep hearing this year and last year about You know buyers are already forming their decision before they get on a call with a salesperson or an SDR or at least a lot of their buying. You know the process has been done up front, and then sure there’s, you know, there’s a buying committee that has to be worked around, and there’s a bunch of mechanics to close a deal. And so There’s still a ton of hard work that sales reps and sales leaders have to navigate. But on the marketing side, the research is being done up front. So creating programs that play into that make it really easy for someone to self educate. Then I think that the best organizations now are figuring out how to Make their buyers. They’re buying committee thought leaders and champions, and that kind of ties into social selling. So one of the things that we’ve been testing, just to give you a more specific example because I know that’s kind of like theoretical and stuff we’ve already heard.
Walter Pape: Yeah. Yeah, give us that 30,000-foot view but Let’s look at those trees and
Elias Rubel: No. Yeah. No. All right, I’ll go down. There’s this new thing that we’re releasing this week called decision maker marketing. The whole premise here is that traditional marketing takes a while. Right. And this is generally where sales and marketing start to split and have their differences is when it takes too long to generate the demand that sales need to do their job well. And so decision maker marketing is a shortcut to go from, you know, what might be a three to six-month marketing program just to get to those results to, you know, a seven to 14 day expedited process which is nuts right and the Way that is by cutting out all of the, you know, traditional method. We walked through it and be like, Have a content brainstorm, figure out what it is that what type of educational pieces. Do we want to make sure that our buyers are reading or engaging with what we know the research we go through making that content? Then we take that we turn them into ads or some sort of paid channel promotion to get them in front of our prospects and decision-makers. And we hope that some percentage of them are going to engage with that. And then we hope that some portion of them will raise their hand and whether it’s a request to them or whatever your golden motion is And then. The sales motion can begin again as a lot of that takes a lot of time so that you can be six-eight Elias Rubel: You know, months out on a program like that. It’s still very much has its place. Even decision-maker marketing says, What if we could just cut out all of that process and go straight to building a real relationship with your decision-maker at the highest level executives executive? Get to know what that person’s priorities are for the year. It’s virtually like a call. Call but disguised and disguised as a bad word. Still, It really, it’s like you’re creating thought leadership with this person, and you’re building relationships in the process. And if there’s alignment, they’re going to acknowledge that they’re going to find that out. So for us, that looks like you know a podcast right or some sort of content creation what we’re doing right now. Let’s pretend that I was your buyer persona; you would take you to know the list of target accounts. I was one of those who reach out and say, you know, hey, Elias. I’m thinking about; I’m doing a podcast on the go to market excellence. Go to Market leadership; we’d love to have you on, of course, now I’m flattered. Right. I’m like, well, sweet, that’s something that I’m an expert on. I’d love to. Thank you for thinking of me; I’d love and so, bam, like, just like that. You’ve now booked a meeting with me. You’re one of your decision-makers in this theoretical example. We’re about to spend as we are right now 45 minutes getting to know each other. And in this program, you’re able to weave in your call questions right like you might ask me something like, you know, the last What’s top of mind for you this year. What’s your biggest challenge. What’s the thing that’s keeping you up at night. I’m inquisitive. Where do you think the industry is going? They could ask me all of these questions that usually would be like pulling teeth with an SDR; you know if sales context, but in this context, and we have a brainstorm. You’re asking me these thoughtful questions. And now, at the end of the call. We’ve built a relationship. And you know what matters to me. And I’m probably curious about what’s going on with you and what your company does, so I almost qualify myself into whether there’s an opportunity there. So that’s decision-maker marketing in a nutshell. And I think that’s something that we see a ton of traction with, and it’s very kind of a tip of the spear in the market right now; companies like
Walter Pape: It is
Elias Rubel: Gone are blazing a trail on this with their, you know, revenue intelligence show, and I think they’re taking a very similar strategy. So they’re great examples in the market of this working well.
Walter Pape: So taking it even further, you’re probably assuming that content that is from this podcast or whatever may be spreading out into case studies and other things to going back to your, your paid advertisement that you’re using, or even more civilly
Elias Rubel: Exactly. If you think about what I describe it to folks, it is like 75% of decision-maker marketing. Building that relationship is the most crucial part, but 25% of it happens to be that you produce a ton of content like video snippets—an actual podcast. You can turn those you know highlights into blog posts, so you don’t even have to think through what we will blog about. You can just hand it off to a talented writer, and they Get to pull quotes from this thought leader who’s also a prospect of yours. Additionally, you can even invite in. In some sense, it doesn’t replace the need for case studies, but when you ask a client for a case study. It’s an ask; right, you’re using it. You’re cashing it in. Whereas if you ask a client. Hey, We have a show that you’re an expert, you know, on this topic and a thought leader; we’d love to have you on and share your thoughts about the industry’s future. You can weave in questions where they talk about how they’ve seen success using tools like yours or whatever it is. And it. I think it’s more potent than a case study because they’re freely sharing it there. It’s not like the canned, before, after, You know, business case ROI. You can still get around to that same stuff, but more organically and authentically without burning that ask as well, which is cool.
Walter Pape: Yeah. So you talked a couple of times about authenticity how that’s key. Why do you think that is like, why is the pendulum shifting to that.
Elias Rubel: You know, I wish I had the answer. I think it’s people who want to enjoy the work they do, and I think we’re starting to see through just the ones and zeros of traditional, and it doesn’t make it any fun to engage with that. And I believe our bullshit detectors are unlike ultimate high alert right like anybody can put together. A case study, but to hear someone casually honestly talk about their challenges and talk about what they’re thinking about. Then you know it happens to be part of your solution happens to be part of that story. You can relate. Right. It’s a sense of relating ability. For the longest time, B2B lost that sense of connecting power, and it wasn’t. It just wasn’t right. And so now I mean, I think Dave Gary hart when he was at drift started to pave the way for this kind of authentic open sharing. Many folks have just taken that and run with it, and now it’s as though the industry has been permitted to be more accurate. You know someone broke the ice people liked it. You see, it turns out we enjoy being human, more than we want is, you know, button-up, you know tie up to them strictly.
Walter Pape: What are you trying to say here, don’t
Elias Rubel: Have a tie on and
Elias Rubel: I still have buttons.
Walter Pape: Oh, I like it. I like it. Um. Oh, that’s so interesting. So I agree. You know, I think it is about people who want to connect with people.
Walter Pape: In a day. I think that’s something that a lot of us are, you know, are craving. I think, especially in today’s pandemic. What do you think it’s been like a second and third-order like wave impacts of being in a pandemic, or from home orders. We think it’s going to happen, you know, moving forward.
Elias Rubel: Man, I wish I had a crystal ball.
Walter Pape: But if you do have a crystal ball, what we say.
Elias Rubel: Hypothetically, yeah.
Elias Rubel: I should just hold an eight ball here. Just as a joke, you’d like, Well, you know, what should we do, like, All right, well let me consult the eight ball.
Walter Pape: Again. Yeah, I mean,
Elias Rubel: There’s the obvious stuff right like in-person events, everybody’s scrambling to figure out on the go to the market size and the growth side, you know, how do we reallocate Those budgets to meaningfully engage with folks who are now at home at the end. So there was a giant pendulum swing right at first. Everyone was scrambling to figure out how to do this. Like, how do we engage with this media in a way that we haven’t before inconsistency in a production value that we haven’t before Great? We’ve got the budget. Let’s throw it into there. But then the pendulum swung, and now everybody’s like, I’m so sick of being on Zoom’s I’m so sick of staring at a screen all day. So I think that’s the new challenge: how do you create unique experiences that don’t feel like a drag? You know they don’t feel like it because pretty quickly, now zoom is getting to be this. The conference where you’re like, man, I just want to go home. My feet are tired, you know, it’s like instead of your feet being tired. It’s your brain and eyes.
Walter Pape: Right.
Elias Rubel: Right. So yeah, I think that’s the challenge right now is coming up with ways to make. There’s a lot you can do with
Elias Rubel: You know this medium. And I think the companies that are going to win will find ways to slice and dice it’s it feels fresh, and if someone doesn’t feel like it’s just another zoom.
Walter Pape: Right, right. So, you know, you mentioned that you work with 510 companies every year, fast-growing. What are some things that are not working? When you go into these organizations, and they’re like, hey, we’re doing these things. What are some pattern matching that you see that doesn’t work, and you have to kind of correct the path?
Elias Rubel: And what’s interesting is a lot of the time, it’s real stuff. You know you. I think when we started down this path, I was expecting a lot more of, you know, very specific in a strategic there’s plenty of that but If I were to identify the most significant pattern here that we see is that companies are rush to ship campaigns that aren’t well matched to their buying committee. And without truly understanding their buying committee and sometimes that happens for later-stage companies that happens when Sales and Marketing don’t have a good partnership or haven’t set up a cadence of communicating with one another, like a weekly cadence of communicating with one another about the conversations that sales. So whether that’s SDR or even an opportunity stage, you know, they’re having and learn like really hearing that feedback. Then bring that over to the marketing side and honing campaigns that either you know help grease the skids so that the deals don’t get hung up. So the buyers are better educated or even targeting just really understanding that that persona and honing in on the ICP. So I’d say if there’s one thing that I get up on my soapbox all the time and rant about, it’s that just like really take the time it’s it’s If you’re about to dump 50 grand 100 grand, you know, a million dollars in a channel per month that you understand our clients range from series A to post IPO. So we deal with all sorts of different budgets, but Regardless, like that money is not going to be well spent, it will fall into a leaky bucket. If you’re, if the fundamental you know piece which is Who are we talking to. What do they care about? And do we have something interesting to say to them that they that not that we think is interesting that they think is interesting? It’s worth taking extra time to nail that down and to test it before throwing a ton of budget behind it. So it’s a that’s, that’s my number one. A pattern that we see folks, you know, everybody thinks they can shortcut right everybody gets a little bit excited. It almost always ends up taking more time than if they just invested upfront.
Walter Pape: Interesting. So how do you tested how you know that you got that messaging and that person. Correct.
Elias Rubel: It’s it’s the sales conversations that validate that right when you have a sales teams like wow, these people are primed right they are eager the messaging, the script everything that we’re saying to them is hitting
Elias Rubel: And they seem well educated about what we’re talking to them out already. They come in, well educated, And then the sales cycles as those shorten up that’s usually a great sign that the matching. They’re both on know at the top of the funnel, who are we bringing into the funnel, who are qualifying the horn. How are we talking to them and educating them and then how a sales are doing in continuing that sales motion, all the way through. So I think the best teams today are thinking about revenue ops, not sales and marketing, right. It’s a team effort. You know, you have top-funnel middle funnel bottom of the funnel and whether you’re in sales and marketing like that funnel. Everybody should be. That’s the thing. Right. And so I think the teams that are better align on that front are the ones that can sprint faster. They’re communicating better, the feedback loop is more robust, which’s essential nowadays.
Walter Pape: So you mentioned bottom of the funnel, and we’ve been talking a lot of, you know, marketing and sales.
Elias Rubel: Yeah.
Walter Pape: How does, how does the bottom-funnel play into, you know, things that you see with these type of companies.
Elias Rubel: In what sense very curious about the bottom phone
Walter Pape: Yeah, yeah. So how are you? How are you thinking about the bottom of the funnel in the feedback loop, you know, once they become a customer? How does that feedback play into your different growth strategies or go to market strategies?
Elias Rubel: Yeah, so I mean as far as I’m concerned. And one of the things we immediately set up. If it doesn’t exist, is there should be a weekly meeting between marketing and the SDR team right so that it’s higher up in the funnel. There should be a doesn’t have to be weekly, but there should be an options review monthly. The account execs to underwrite between marketing and account execs to understand what’s going on and the opportunities. Where are they getting hung up? What’s the feedback. And then likewise, you know, maybe, it isn’t monthly, but at least at a bare minimum, it should be monthly, but at a bare minimum, it could be quarterly with the success team. Understanding, you know what, what are those stories of success. Whereas, they’re still friction, and how can marketing support, you know, the places where there are friction and champion the sites, and the customers were their success. So that’s critical. Yeah.
Walter Pape: No. So, so to me, it sounds like you. You’re not only just talking about what you can do for marketing from the buyer perspective; we’re also thinking from sales. Through just, you know, simple conversations are what you’re seeing is, you know, tactics that people can implement today to make their go-to-market plans more attainable.
Elias Rubel: Oh yeah, I mean, Players Sometimes when as a team, you know, like it’s funny how early teams will silo themselves. And it’s just like such an easy adjustment. If you can take a step back and go, Okay, let’s just think about this as we’re a funnel team or revenue team. I need to communicate at certain junctures On a certain cadence so that everyone. Everybody can be in lockstep, so yeah, it’s Super key’s we didn’t expect to spend so much time on organizational coaching and on, you know, these, these bits, but they are the fundamentals everything else follows from. So those have to be set upright in the beginning. Yeah.
Walter Pape: No, it’s interesting. So, and you mentioned earlier about DevOps as An essential piece. Can you expand on it? Or why, why do you like, why did you bring that up. Like, why do you think that’s like an essential piece.
Elias Rubel: Because if so, When I think of revenue operations. I’m thinking of like the the the merger of sales And marketing, right, if we take away those titles like it is revenue operations is the plan, the strategy, the goals. The measures and the two teams that play into the various pieces of the funnel. Right. And so I think that like I use that term, to sum up, all of those pieces. These, if any one of those, gets out of whack. Right. Like even if you know when the CEO, CFO, sets benchmarks with the board and the CEO and others. Like, if not everyone is present at the table and bought in on those goals. That’s, again, you end up with these fit like Fisher’s between groups and people not pushing in the same direction. And then you sometimes end up with like arbitrary goal setting, which is the worst. Like, I think we’re getting away from that. But, you know, If you comp a marketing team on an SQL goal, which is the wrong thing to be measuring right, who cares how many MQ else there are if marketing is contributing to Opportunity creation and revenue creation. Right. And a lot of the time, I mean we’ll see companies clients of ours who will bet about their MQ L’s. You know how many calls they need and like, no, no, no, like, Our goal should be to support however many opportunities we need to create based on what we know our average close one ratio rate is To help whatever revenue we know we need, and in that way. We’re also aligning ourselves with the sales team because if they’re not getting opportunities. And they’re not closing those opportunities; they’re losing. So why would marketing not fail in that case? Well, we hit our SQL goal like that. That doesn’t matter.
Walter Pape: Because
Elias Rubel: The people who matter. The ones are closing the deals and supporting the companies if they’re not happy, we’re not, we shouldn’t be satisfied. So I think that that’s almost becoming old news, which is excellent. Like, I guess, modern marketing teams are thinking in this way, and they’re partnering with sales, and they’re setting the goals in the same room together. But that certainly is something that if teams aren’t thinking about it that way, yet they should, they should think about it that way.
Walter Pape: Interesting. So if you were to give somebody advice that they’re thinking about more, the SQL at sales qualified you to know opportunity created That you know your traditional pathway. How do you start having that conversation? How do you get to a point where it’s lining up to be that opportunity creation. How would you, where would you advise people to start
Elias Rubel: Simplify just, you know, like, Get, get the two leaders in the room or three leaders in the room and say, what are we like, what are we even trying to accomplish here. What shuts this company down what? How do we fail? And how do we win? And it’s probably one number or two numbers, maybe, you know, like, what is our turn. And thereby engagement, all these things customer success customer happiness. And what is our revenue? Right. And of course, there are others I’m speaking purely on, you know the house’s revenue side, right, but When you boil it down to just what matters. Then things become a lot more straightforward. It’s like okay like marketing team what like They can say the sales, like how many. What do we, what’s our win rate. Right. Okay. Based on that, now we know how many opportunities we need to create great we’re going to wear your partner to make sure that they are completed. And then you’re our partner to give us feedback if we’re doing an excellent job of creating opportunities, but that there, for whatever reason, not closing. Well, or they could close. It could be a better alignment. They could complete more quickly right you you partner with us. Let us know about that will partner to make sure that you’re getting those at-bats in a meaningful way. And our only our, our goal is closed one revenue and making sure that those are customers that are retained. So, those, those are yours. Those are two
Walter Pape: guiding star for your
Elias Rubel: North Star, for sure. Yep.
Walter Pape: Awesome. So once I have been noticing a lot about it’s, you talk about frameworks and how to think about things from marketing from revenue to operations to sales. I mean, where did all these different ideas and frameworks come from, like, like, how do they develop and where do they come like yeah, where did they start
Elias Rubel: Yeah, I mean, I think it’s just you make a lot of painful mistakes along the way. Right. Like I can call out a time when I had an awful partnership with a sales leader. And I think both of us fucked it up in fantastic ways. I mean, we were just like, doing all the wrong things together in our partnership. And it made it so contentious. And so I was not optimized for company success due to how we chose to partner and how we were thinking about our goals. That was the genesis for me of The first big slap in the face, with this kind of more organizational and objective setting. Indeed, we’ve been through many more examples where we see this being done pattern match and say, Okay, let’s call us out early. Let’s fix it. Let’s help them get on the right path. But for me, there was one in particular where We both weren’t doing it right. I made a ton of mistakes, and I certainly think he did as well. And I’m sure now, in retrospect, we would see that, and we would probably laugh about it and go wow, you know we could have done so much better together. But I think sometimes you have to learn the hard way. Know, have some of mine. Some of my best business learnings have been the hard way, for sure.
Walter Pape: What’s another one that comes to mind.
Elias Rubel: Oh, man. They’re so bright. I think there’s a lot about when I usually go through these, and I jump back to the founder stuff. Right. And like the, you know, not necessarily with matter made today, but I’ve had several other companies. Two of them that were acquired, and so I mean everything from founder mistakes. You know, like picking. How do you choose the right people to work with? How do you evaluate those folks and You see, I’ve been through many founder breakups and replacement of executives and all these things that, you know, until you’re in the hot seat, trying to figure out, like, do I need to part ways with this person. Do I need to bring someone else in, do I like You can’t learn how to handle that until you have to learn how to take it almost like I don’t think there’s any class theory or You know, Harvard Business School papers that I could have read that would have prepared me to handle those situations. You know what happens when you sell a company and then end up in court over payment disagreements right like for the payout like this shit. You don’t think about it; you’re like, oh, hey, you know, like, we’re good.
Walter Pape: Awesome. And then, you know, like things come up and you have to deal with them, and you have to learn on the fly.
Elias Rubel: And thankfully, you know, I’ve been fortunate to be surrounded by some talented and helpful mentors and whether it’s formal or informal along the way. And I think those are the moments where You lean on people like that who’s been through it before and can advise, and you come out the other end than being able to do that yourself a bit better.
Walter Pape: Absolutely. Well, I want to get back to those opportunities, talk about your mentors in a little bit. I would be curious to dive into how do you think about recruitment. I mean, I go to market plans for any level for a founder to an operator, you have to make good hirings. That sounds like he was a critical learner for you. How do you think about it now?
Elias Rubel: It depends on what level. But typically, the first thing so okay for the longest time, I kind of chuckled when people were like culture. Culture. Culture. Culture Like, all right, sure, but like rubber meets the road. People need to be talented and have experience. Still, I’ve made enough bad hires through my career thus far to realize now that like culture and Team Fit is the most important thing because if you get someone who is a bright mind who Thinks on their feet, culturally is align. By culture, I mean many different things like it matter made One of the most important things is that people take Extreme Ownership right, so if something goes wrong. It’s that person’s responsibility to fix it. It’s my responsibility to everyone assumed as I’ve got, I must do something because we don’t accept that, you know, Stuff to go wrong, like that. Everybody jumps in, everybody picks up in, or everybody’s paddling together, but that mindset is sometimes hard to find. Certain people just enjoy being in their swim lane doing their thing and not thinking about things in such a proactive way. I think culture. Then also expands into like how to how to individuals feel about corporate responsibility and are necessary involvement in community projects and community impact and so Nowadays, where I’m seeing the most success is finding people who line up with those principles just naturally not because they want the job, but because this is already. This is They’re actively seeking for a company like this and. And I’ve found that most of these people also happened to be highly skilled and again happen to have fascinating backgrounds. So that, that’s kind of Where I think about how I feel about recruiting today is looking for that kind of diamonds in the rough that are aligned on that front. And then, of course, going through, you know, skill set. And, you know, giving them practical experience to see how they handle situations and all that.
Walter Pape: That’s good. I like that, especially like you can give them like that you find a rough diamond, but you still verify. Hey, you can do the job. And now. Okay, great. Like culturally, you fit with the principles because you were seeking us out or for whatever reason. No, that’s, that’s interesting. So can I shift? You’ve two companies; you’re doing five to 10 large scale growth advising probably different companies. How do you do it like? What are things you do for yourself, like what processes or habits have you formed to help you today?
Elias Rubel: Good question. I do my best to keep my mind clear; that sounds stupid as it’s coming out of my mouth. Still, by that, I mean I try not to overwork myself because I find that if I let my days drag out and I’m not regimented about how I’ve used my time during the day. And I start logging too many hours. I just fall into this rut of pure execution, and that’s not what you know I wouldn’t. That’s not the top priority when people come to us that, of course, performance is significant. Right. But it’s like table stakes almost that it’s the thoughtfulness behind the execution and some, like, as we talked about earlier. Sometimes you have to simplify things down. And have that, you need to have the headspace to simplify things down in the first place. And so for me, I’ve in the last couple of years, I’ve become much more regimented about like, when is my day starting to end. How much time do I give myself between meetings to like process and clear out and start fresh for the next person? I’d say that’s a really core thing that has helped me and helped our clients see more success. Because I certainly you know we’ve all been there, grinding it out. Your brain just like steam coming out the ears, and you’re just trying to stay above water, and that’s not helpful for anyone. So I’d say as far as a personal toolset, that’s at the top for me.
Walter Pape: Yeah, now are you doing this, like, the day before the morning of the week before, how do you kind of plan out your, your day today
Elias Rubel: Yeah, I mean, it’s I work with an assistant who helps keep my calendar straight, and she’s fantastic. And we have a chief of staff that Makes sure that all of our everyone set up for success in the meetings they’re having and that. You know, we’re all enabled in the way that we need to be, even though it’s kind of funny. Like, we’re a small team in the scheme of things, right? We’re like between 10 and 15 people depending on how you look at it, and We don’t work on paper. We don’t need a chief of staff, but this person enables us to do our best work. And to have the most transparent minds and so I would say that that for me, like when I’m chatting with folks who are trying to be too high performance and Optimize the most out of their time the advice that I give them over beers, rather than saying like Man like cram more into your calendar is to say, hey, what can you take out of there. How can you cram less than your calendar and I always recommend finding someone to work with. Even you know, even if you don’t think that like I have it under control, or I can manage it. Like my output is the equivalent of three of me because of the person that I work with. And she indeed enables me to be a much better version of myself, you know, we’re context and a personal context. While keeping my mind clear. It’s, it’s, I kind of was slow on the uptake of going down that path. But I’m thrilled that I was convinced to do so. There’s I’ll send a wreck a recommendation out for everyone listening. There’s a company called mind Maven that was started; it’s a consulting group. It began with a gentleman who was in charge of I’m going to space. The division that he was in the order of it at LinkedIn early on LinkedIn. He was in the order of like the network effects of the product or something like that. But I was thinking about how Networking works and how people build trust in one another and has a consultancy that helps folks help leaders make more meaningful relationships while using effectively less of their time leveraging an EA and called yeah my Maven. Check it out. It’s powerful stuff. We worked with Connor is the name of the guy that we worked with there. And I would spend that money 15 times over to get the results that I have.
Walter Pape: Also, well, we’ll add that in the show notes. Make sure that everyone gets it. So that’s an excellent recommendation on recommendations like any other tools resources that you found to help your day-to-day execution.
Elias Rubel: tools and resources. I’m a big fan of grain and D script. They do similar things, but the grain is a newer company that plugs into your zoom and allows you to create like highlights snippets from conversations based on text. So it’s mighty. If you’re trying to produce content from your zoom meetings, I highly recommend checking that out. They have great integration. Let’s see, the script is very similar, but it doesn’t integrate with zoom. So if you’re having a lot of meetings or not meetings. You have video content that isn’t coming from zoom recorded elsewhere, and you need to upload it into a tool to edit it quickly and create highlights. It’s an excellent tool for that. And there are so many tools. I’m just trying to focus Focus my mind on something that would be helpful. One of the things that we like doing is as quickly as possible; having a dashboard cockpit. For, you know, both at the executive and board level all the way through, like, what is, you know, the CEO care about seeing and reporting to the board. What does the CMO care about having at their fingertips, like what You know, what does she care about seeing at a glance? And then what is the team underneath that person care about being able to deep dive into with like campaign level reporting and boards? A data box is a tool that we use for that. And I think it’s fantastic. And worth checking out.
Walter Pape: All right, I’ll add down below in the show notes. Wherever this will be so, you’ve been a founder Now, helping companies with a marketing somebody who is either thinking, hey, I want to become a founder or want to get into the marketing, or I’m just starting, what advice would you give them.
Elias Rubel: Start
Elias Rubel: Start reaching out to people I that was, that was the genesis. For me, I come from a very nontraditional business background. Like you know, I went to art school. I dropped out of art school; I founded my first company after waiting for tables. So I didn’t have any like if that first company hadn’t succeeded. I wouldn’t have had any criteria by which anyone would have hired me for anything, right, like I just didn’t I wasn’t qualified in a traditional sense. I knew that I had to prove myself through that. And so what I did was Reach out to just a bunch of people who had been successful in the arena that I cared about was interested in And was honest them was like hey you know you’ve been wildly successful I have everything to learn I’m you do eager just to hear your story and to learn from you. And you know, I have nothing to offer in return, except, you know, open ears. Hopefully, someday we’ll be able to have beers and talk about how your advice. Was impactful for me. And I think that spans both if you want to found a company or even if you’re at the beginning of your career in growth or marketing. And you want to accelerate your ladder up in learning and growing and titles and all that responsibility, I think. Same thing as Surround yourself with people who have done more and better and continue to push yourself to do that. The only moments in my career where I’ve felt stagnant are when I stopped reaching out to people and stopped going myself to think about what is above and what they are doing.
Walter Pape: That’s excellent advice. Last question. You want people to take away from this conversation hard that you want to leave with them doesn’t have to relate to the dialogue just, hey, this is something that I want to go with you and in our time together?
Elias Rubel: Yeah, I think about how you partner with people, whether those people are, you know, internal and team. It’s A new visual level like just another person on your team; how I think about how you’re partnering with that person are you doing something that is going to help them be a better version of themselves, or that enables them to be the best version of themselves. There’s a quote about find some find one thing to do. What one thing can I do today to increase the energy of my team And I think that that applies to both leaders, and I sees right everyone has the opportunity to do that, and groups that have the most fun are the most effective I think, to push themselves and one another to think about how they’re enabling each other. So that’s one thing. Another thing that I wish was talked about more and more action was taken was asking ourselves as individuals. Again, whether we’re an IC or a leader or a founder or VC. I think we have tremendous influence in the world today And: I think we need to do more with that influence in our communities. And not just talking about and not just supporting it with our words, I think Marc Benioff is such a great example of this, where, you know, there was the Law that was up. I’m going to butcher the specifics, but I think it’s like North Carolina and the bathroom gendering the bathrooms. And he was like, You know what, we’re done doing business. If you guys aren’t going to be supportive of everyone in this world, like we just will pull out of North Carolina, as a whole, right, and I think he’s done this a couple of times now. And I think that yeah, it’s Salesforce, and yeah, they could probably afford to not be in North Carolina or whatever state. It was, I apologize, North Carolina. If it wasn’t you, but I think it was, But I think we have a lot more power than we realize and have a lot more skills than we learn. Finding ways as individuals and teams to lend those skills to our communities and causes that will impact us will affect our children. We all need to think about that more often, and we’ll talk about it more often.
Walter Pape: No, absolutely agree. I think that’s, that’s good Elias, if people are interested in, you know, reaching out to you or want to get to learn more. Where should people go
Elias Rubel: Yeah, I mean matter male Co. To learn more about matter mid and then connect with me on LinkedIn. I’m always happy to have conversations with smart folks who are doing exciting things out there. Or folks are the beginning of their career and trying to figure out what they’re doing. Regardless, Elias ruble on LinkedIn.
Walter Pape: All right, perfect. I will add those to the show notes as well and allies. Again, thank you so much. It was great chatting with you today.
Elias Rubel: Walter. Always a pleasure, man.
For the first episode we have Ryan Williams. You can find him on LinkedIn at /jryanwilliams. Ryan is the Co-Founder of Churro Media and producer for a documentary “Outside the Valley” which can be found at outsidethevalley.tv and executive coach at jryan.coach. Where he coaches executives, emerging leaders and veterans transitioning into civil workforce. Before all of this he has seen the journey of 0-100 million 3 times as an advisor and operator.
In this conversation we cover how he started Churro Media and film his documentary. What 3 things come from writing out your sales process, becoming an expert, advice for sales reps, and thoughts on the upcoming year. This show has a little of everything for everyone and I hope you enjoy it.
Let us know what was your favorite quote or lesson from this episode? Please let us know in the comments!
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“The views expressed on this post are mine and my guests alone and do not reflect the views of Zoom.”
Show notes and Transcripts
Click show more to see full details.
Why starting Churro Media and the story behind the documentary, “Outside the Valley” [:50]
Ryan sharing how talking to Founders outside of the USA was the catalyst to Churro Media [5:50]
Observations from working internationally and effects of COVID-19 on fundraising [8:57]
How VC’s are approaching this time between early stage vs late stage bets [10:20]
Vintage of Startups that will come from COVID-19 [11:20]
Ryan’s background in advising and VP of Sales : [13:30]
Why you should write out your sells process [15:05]
What does your buyer say when you are not in the room? [16:05]
How writing your sales process allows you to create experiments as a Founder [16:56]
Advice for sales reps to stand out [17:30]
How writing out your sales process helps you identify what type of rep you should hire [18:20]
How writing out your sales process as a rep prepares you for running your book as a entrepreneur [19:25]
Why finding pattern matching matters [20:30]
What it takes to become an expert [23:55]
How it applies as a sales rep [25:00]
Examples of meta questions that Ryan coaches on [28:38]
Ryan ties meta questions with a story about a big career decision and an observation by his wife. [29:42]
How Ryan created his perfect day [31:00]
Questions to answer to optimize for the best experience [34:40]
Interview questions to ask to identify fit [35:00]
A question that reveals bias and reveals what people care about – [36:00]
Message for the listeners [37:45]
Walter: Ryan, welcome to the show.
Ryan: Thank you.
Walter: Great to talk to you.
Ryan: As always.
Walter: As always. Well, Ryan, super excited to have you on as the first show. And we’ve known each other for close to what, five, six years now. And a lot of conversations that we have. It’s been that long. So excited to now record one of these. So with that kind of you know intro, I want to hear more on why did you end up starting Cero Media?
Ryan: The story’s actually really funny, I guess. But the easiest way to frame it is I had no idea what I was getting into when I said, I wanted to become keynote speaker. And so I just kept volunteering for opportunities to speak. And mostly this is around startups, how do I help startups. At the time, I was VP of sales at Lead Genius, an YC back Data Company. And I was just putting myself out there as let me see how I could be helpful. And, a lot of that it was doing sales talks. That led to a really interesting experience at 500 startups where they have the smaller accelerator programs around the world. And so they asked me to go to Kobe, Japan and do two talks, that kickoff keynote, and then close down the first week, and do a reflection experience and do like a closing keynote for that week. And I was giving that talk, things were going what I would consider well, as a speaker. I was feeling like I found my flow, I looked up and the translator looked like she was gonna kill me because I was talking too fast. I was cursing which was not acceptable. Or not advised. And I got to the end, and the guy who is running this accelerator pulled me aside on the way out, I thought this is it. This is the talk from the principle, hey, you’re never doing this, again. Your keynote sucked and stop cursing to a Japanese audience. And Max is his name, he pulled me aside. He said, Hey, that was great. Can you meet me in Uruguay and do the same talk in six weeks? And I was like, Holy smokes. All right. So I was like, great, happy to do it. I had to look up Uruguay on a map by the way, I had no idea where that was. I thought it was like it rounded Paraguay, whatever. I’ll look it up. And so I’m headed back to the airport to leave this trip from Kobe. And I’m realizing, oh, wow, what I’m doing is actually really valuable specifically to founders that are outside Silicon Valley. And that one talk led to now what’s been 20 events at accelerators around the world in 14 countries. I’ve met probably 2, 3000 founders. The largest talk I gave was a follow up to that Uruguay experience. I gave a talk to 750 people in Uruguay. So like the, I want to be a keynote speaker idea, that work that stuck. And along the way, I reconnected with a close friend from college Hannah Wicks. And Hannah has seven films that have gone on to be Netflix sized documentary hits. And I was telling her what I was doing. And we actually cross paths in Italy on my way to Istanbul for another startup talk. And so when we cross paths, she just said, hey, you know, there’s something really interesting here about why these companies are having you come out and speak in these, what we call ecosystems, right? These group of startups in Istanbul, these group of startups in Buenos Aires, these accelerators, these events. And that led to a development project where we went to four cities, filming about the city. And we even shot a pilot for more of a reality TV series that went nowhere. But it all led to a process of saying what we’re doing here is actually telling stories of founders from around the world. And we just finished our first feature documentary. And so Cero Media is the holding company that now has two media projects that you’ll see a little more coming out this week as the trailer for our first feature film called Outside the Valley, the early years. And it’s about early stage founders in Portugal, in Uruguay, in Mexico City where you’ll meet Andy and Maka, who are basically bringing e commerce. You know that e commerce is a space has had a 20 year head start, but it’s still fairly new in Mexico. And then we end that story in New Zealand just before the Coronavirus stops us from getting into our fifth city. And so that’s the first media property. The second is a docu series called Future. It’s also powered by Uruguay because actually in Uruguay, we made the connections of folks who want to tell more of their stories of the software that’s being developed in Uruguay and going all around the world including using for facial recognition in Africa to identify lions. Lions have unique whisker patterns. And so we’re finding all these amazing stories about technology and software and startups and founders. And we’re putting all that together in what’s best to describe is like one channel, you know. It hasn’t emerged as a channel yet, but the people who join this community are going to see stories from around the world. And that’s really what Cero Media is about. Did I answer your question?
Walter: You did.
Ryan: It felt like I gave you a long answer, but that’s what happened.
Walter: Yeah. But that’s the nice part about this, is that your poster, you know, go off and font format, so feel free to speak. It sounds like quite the adventure. And a lot of time and energy went into it. Like why are you doing this? Like, what itch is that scratching for you?
Ryan: Well, there’s a couple things, right. One is, this work. As I’ve met these founders, the work of telling their stories is an absolute love letter. The amount of grit and determination that happens for founders that are outside Silicon Valley is so impressive, because you sometimes have founders who are running a company in their second or their third language, they’re not getting advice and podcasts and the way that we consume material in our startups, or sales process or growth strategy or fundraising, you know? Think about all the challenges, right, it’s easier to raise money, when you have a similar background to the person who’s giving that money out, because there’s less object from. But if you have an accent, or you’re from somewhere else, or you look differently, or you’re a different gender than the person who’s writing the cheque, it gets harder. And there’s lots of studies that proves how hard it is to fundraise, which is one of the first basic things. Like knowing that you’re a technology company means that you’re using tech as your lever for growth and success. You know, that’s why we call it disruption, right? It’s because tech is that lever. And a lot of times to be able to use that tech to be able develop that tech, you need to raise money. Fundraising is not something that everybody around the world can just go turn on the way that if you know went to high school in Palo Alto, you probably have somebody in your social network, who’s gone the venture route, or gone the early stage and, you know, Yahoo or whatever, you know, company, depending on your generation, and they know somebody who wrote the cheque, or can write the cheque, read an angel cheque. Having angels in these communities, it’s hard too. And so for us, what we’re really excited about is just you know, the love of that founder, that person who’s going out there staking, going on the way they’re you know, they’re burning the boats, they’re going all in and to be able to kind of give that founder a voice and share that. What we’re finding is that there’s a lot of people who want to hear that story, because they’re on the fence thinking about their next thing, right? They’re thinking I’m about ready to jump in, which is funny, because that’s actually my co-founder, I met in college, doing a college project. And he went off into the startup entrepreneurial route. And, several times had invited me to join him. And I always considered it a regret for not doing that, you know, and here we are almost 20 years later, back to the well, this turned in from let’s do a short film project, just released to my audience around sales and coaching too. There’s actually a much wider audience than they want to see some stuff. You know, along the way, you get to see me, you know, fall off a scooter and, you know, meet somewhere and talk to some locals about what makes their coffee different and things like that. And that’s really the fun stuff that makes telling the stories so much fun.
Walter: Yeah, no, it’s very interesting. I think also with the COVID pandemic, and people working from home disruption from that, it’s probably going to level the field in a lot of different ways. When talking with all these international founders, what are their thoughts? And what are your observations?
Ryan: Well, fundraising is you know, they say that fundraising has not flattened off with the pandemic in the way that people thought it would back in March. People thought, Okay, this is gonna be really hard to get a cheque. The thing about the VC economics is that the money is already there. And so some early stage VCs are sitting on it, saying, hey, I’m gonna wait till startups get cheaper, you know, so my friends that do early stage, kind of pre series A cheques, cheques that are usually 100 to 200 K, less than a million dollars, those folks are kind of playing a waiting game to see who’s gonna survive this because that shows enough grit that they can then invest. The next stage up to series A and Series B, those are funds that already have money in them. The LPS have already had capital call, there’s money in those coffers. And so then it’s a question of, how do we keep our management fees alive if you’re a VC, and if you need to, then you want to keep your pipeline going, you’re taking those calls, you’re doing over zoom. And it’s easier because you know, the way you get to know the founder is a little bit different. You know, you’re able to like, you know, sense, you know, do a call, get a sense of them, be in their life, I’m sure. I mean, I’m sure you’ve seen all the zoom calls, it means that you get to see inside people’s offices and homes, things…
Ryan: And see how they manage their life, see, if they’re like, let me put you on mute. And then you hear them, you know, you can see them invisible yelling at their children to get. You can see all that stuff, you embrace that. But what I’ve also heard is that a lot of the fundraising not slowing down statement is, there’s a lot of late stage, you know, we’re going to use that money to make a bet that we already have the rest. And, I think that’s really interesting in that it still may be hard to get some of that early stuff done even though we say it’s getting easier, you can do it from all the way around the world. Zoom calls, people will know you change your background, people will know where you are. And so you can tell them that, you know, we’re running this company out of Palo Alto. Right now, you’d probably think that’s pretty silly, based on the price per square foot in Palo Alto. They’d like you to say, you know, Denver or Tulsa, you know, or somewhere else, that’s a little more cost efficient than San Francisco or the valley. So it’s interesting, it’ll be you know, I hope that what happens, you know, a lot of folks on the investment side talk about startups as vintages. You know, there’s a vintage of startups that we’re all trying to be like Groupon, they all show up at the same time, because the problems are the same.
Ryan: It’s not that everybody followed Groupon, there’s few that followed Groupon but the problems that were being solved like box and Dropbox, you know? They started a couple years apart, but they had the same origin stories where, you know, we’re in the dorm room, or we’re, you know, in our first job, and we don’t like using thumb drives or emailing stuff to ourselves, the stories are the same from about the same era. And so I’m just worried that COVID is going to show us that there’s a vintage ticket made. One of the, you know a wine producer that I absolutely love that I can barely afford, just sent out an email and said, hey, you know, our grapes, they survived the fire, but this, you know, they were too close to the heat. So we were not going to make our vintage because it’s not gonna be as good. And so why is there a vintage where some people are deciding that because of the fires in 2020, they’re not doing it? And I think there’s a lot of startups that will not survive this. And then there’s a lot of folks who are happy in their corporate jobs, they’re investing so options for companies that are doing well, there’s a lot of virtual companies that are doing well. And, then they’re going to be able to start their thing in early 2021. That’s where we’re gonna see a lot of innovative seed stage companies coming. And, they won’t necessarily launch it early 2021, that it might be to the summertime that you start to hear about their launch. But they will raise a small cheque, they’ll raise 100 200 K, or whatever they need. And that’s where interesting stuffs gonna happen.
Walter: Now, that’s going to be really interesting on what’s going to be some of the rippling effects of COVID. And thinking about also the economy, and especially within the VC world. So getting into the original reason why you started doing this is being a keynote speaker for sales, you have done three times, three companies YC Bank, zero to 100 million, when you’re now looking at all these different things, what are some things that you’re thinking about as far as go to market fit, how to grow? What are your advisement on how companies should be doing that in today’s market?
Ryan: Well, I think there’s two pockets of advice, right? There’s an advice to the founder and the startup. And, you know, thinking about it and preparing for this conversation, you know, I’ve had the fortune of seeing as a coach, I’ve seen the 50 to 150 million journey working with high growth, high potential sales leaders, the director of midmarket, head of SMB sales at companies that already have some great traction and some you know, amazing growth metrics. And I’ve also seen at the founder stage as an advisor, I was an advisor to a company called Envision back when they’re about 10 employees. They are around 2000 employees now, they work with every one of the Fortune 100. And so I’ve seen the founder trying to go and make that first sale. And then I lived it at Admiral when I was, you know, the first sales manager, I built a $22 million sales team or a $58 million sales team in 22 months, and had a chance to work with around 250 sales reps, and SDRs over the course of my four and a half, almost five years there. And so I got to see how to sell myself into that world and then what happens when the company takes off. And I’ll tell you that across the board, there are some very fundamental things that just have to exist for companies to get it right. That is, knowing what you’re doing, knowing how you sell. And so anybody listening to this who doesn’t have a written out sales process, stop right now and write out your sales process. And then take a different color pen and go right underneath it, what the buyer is doing in every one of those steps. So when you get to the third step and you know, like, let’s say your sales process, step three is doing a demo for your buyer, and that buyer is boss, let’s say, I expect there to be two or three people on the call, I’m going to demo the software, here’s what. On the third step might be internally, they’ve got to go ask their boss, Hey, can you join this call? What is that conversation look like when you’re not in the room? When your buyer is turned around and saying to somebody else, hey, it’s really important that you sit on this demo, because I need to buy this event management software for the event that we’re doing in March. Okay, what’s going on at that stage? What’s that conversation look like? I don’t really want to do this. Or great. Can you expose me to all these? I want to actually I want to hear from three vendors. Like what is that boss ask for? And then if it is, I want to hear from three vendors. Your sales process might be doing a demo, and then the next week, you’re asking for the order. Well, that’s great that you think you’re asking for the order on the next week. But there’s process might be to interview two other companies with the same questions that you gave them. As you showed your demo, they took notes. And they said, All right, and they ask all your competitors to rebuttal. What do you do about this feature? What do you do about security and the things that you think are the best points of your sales process. And so by writing your process out means two things, one, you’ve written it out so you can be intentional. Three things really two, you’ve written it out so you can think about what your buyer is doing. And three, you’ve written it out so there’s a line in the sand for your experiment. If the last five conversations you had all of them went to demo, and foreman went dark, well, either you have a 20% conversion rate from demo to the next stage, it might be negotiation, or that major drop off has shown you that your message is not working four out of five times. Which is it? I don’t know. But you’re not going to know either unless you’re documenting or writing some of this stuff down. Right. So I think that’s advice one, and that goes both ways. That’s both the founder who’s starting to sell for the first time, they’re going to use that same process to identify what sales rep they should hire. They do the same process we just talked about. And they discover that, you know, the demo is not that important. Because the demos are fairly easy. And then it’s a matter of waiting for time. And they know they’re going to win against the competitors. And it’s the story that I just made up. Well, great. Now they know that they don’t have to hire somebody who’s really adept at giving demos. If the reverse is true, they’re losing four out of five demos. They need to hire somebody who’s got more credibility, they might save up and spend more money on hiring a sales rep account executive or somebody who’s slightly more senior, who has experience doing that type of sales process. This morning, I started my day talking to a, you know, brilliant sales leader who has previous experience selling billion dollar deals. Walter, how many people do you know that can say that they sold something for over 100 million?
Walter: I would say right now…,
Ryan: Do you know anybody?
Walter: No body. Not the top of my head.
Ryan: Right? So same here, right? So this dude worked on a billion dollar deal, it was a three year deal selling something to the government. And I won’t get into specifics, but you know, he’s basically it was a piece of hardware that helps for monitoring logistics.
Ryan: You know, you need to ship some containers around, you need to monitor them, who’s got a bunch of containers moving around? Well the government has one of the biggest logistics operations, you know, the US government does.
Ryan: And so, you need to track all those containers. Let’s just, you know, keep it like that. And so anyway, but you know, okay, these are really big engagements. This is somebody who have you said, hey, how do I optimize my sales process? And what you’re selling is maybe an ad on Yelp, 300 bucks to a single decision maker one call close, you know, they’re just, it’s just a different world, right? And so if you’re somebody who doesn’t have a sales process right now, other than what’s in your CRM, if you write it yourself, and you make some of those assumptions, then you can also see what type of rep you are. I’m really comfortable at a 30 day sales cycle anything past 30 days, I usually lose. Is that because of me as a rep, is it because the product I’m selling? Well, let’s have that same data, and any sales rep who’s brought that kind of data in to me, and when I was a hiring manager, always is going to get more consideration for that job than anybody else. Because they’re showing me that they’ve got the skill of being able to do the job and the skill of being able to think about the job they’re doing. The founders usually have that because they’re constantly thinking about what they’re doing. They have these Meta conversations in their head that in some cases are just haunting. And it’s tough. It’s tough. They’ve got the hardest job in the room. But then you come down to you hear a sales rep who can do the same thing. Okay, man, you’re running your book as an entrepreneur. That’s really cool. That’s really interesting to me.
Walter: So they’re able to outline the selling journey, match it to the buyer journey and do experiments along the way. Outside of doing that, is there anything that you think that people are doing wrong today, they also should be focusing on?
Ryan: Well, finding patterns. So as humans, we always want to find patterns. You buy a white car, I bought a white Subaru when my first car it was actually the Subaru Legacy wagon. And the outback trim, I don’t know when the outback came out. It was a 97 legacy wagon, it was white, and it had just a gray paint job that made it the outback. It had gray paint, heated seats, and a weather radio. That’s what made it Outback. Since then, I think Subaru has gotten a little fancier about their Outback. So they’ve done some things in the trim. As soon as I bought that car, every other car I saw in the town I was living in was white. You drive a white car, you pattern matching, you see white cars. You go to Stanford, you see a bunch of other people who also went to Stanford, you’re an investor, you’re going to invest in people that you know, that went to Stanford, because that’s what you know, is pattern match. Now, there’s a lot of problems with that. But there’s also a lot of good that comes from being able to naturally match those patterns. And so the question that I have for a sales rep who’s trying to, you know, trying to get ahead, and you know, and founders too, but I think founders are going to do this naturally. But salespeople need to do that same pattern matching of the last five deals I want, what do they have in common? Can you tell the background that my zoom school is not going that? Well, it must be recess time or lunch because they are going nuts upstairs right now. So I hope it’s not killing your audio.
Walter: It’ll be fine.
Ryan: But, you know, they’re having fun, at least, you know, I hope they look at this is the year of their life that they got…
Walter: Online school.
Ryan: Yeah, absolutely. So let’s talk a little more about this pattern matching thing. So I want to give a quick shout out to old friend long time ago worked with this woman named Megan. And she made an effort at Admiral to sell all of the high fashion companies in London. And she was really into things like handbags, the stuff I don’t know a lot about, but she made it a point to talk to all of these independent designers who had ecommerce stores. And she had a very tight aperture tight view of this is what it means to be a fashion e commerce in the UK right now. And that was Intel we really needed. Somebody else at the same time also early on the Admiral team is a man named Ben Willy, and Ben was doing the same thing, but he was selling to a dead end market for us, but he was learning a ton about selling it into India. And so he had talked to you know, maybe 200 potential advertisers in India and gotten some of them too close. But he had developed enough of a pattern to understand the market India that he was getting called in from the CFO. And that job turned into a product management job. Now he’s a founder, he’s running a company called Recess which is a really cool breakout beverage from the last two years. It’s a CBD sparkling water type beverage. But because of this pattern matching he will be able to say okay, well, I tried the same thing 10 times, this is what I had in common. And sales reps who are looking for leadership opportunities, need to think about a way to do that where they become the expert in this market. You know, a lot of people are familiar with the advice that you know, takes 10,000 hours to be an expert. It comes from a research study that Malcolm Gladwell wrote about in the book Outliers.
Ryan: Well, I had a professor in school, Colin Campbell, who was one of my favorite professors. And he actually he gave us an assignment over break. He said, if you go home with a break, and you read every book that Edward Abbey wrote, Edward Abbey was a western US, writer, you know, probably 50s and 60s, I want to say. And if you read every one of Edward Abbey’s books, he wrote nine books, let’s say you only read eight of them. But you got an eight week break between Thanksgiving and New Year’s because we have this really long winter breaks at the college. And so if you went and read all of his books, you’d come back and you’d be the Edward Abbey expert for about 100 miles, except maybe there’s a professor who wrote his dissertation or her dissertation on Edward Abby. In which case you should probably choose another author. But his point was, it doesn’t take much to become an expert. Okay, now let’s go back to the sales rep advice. A sales rep selling hotel management software to the GM of a hotel, who hasn’t more than three weeks on the job, has looked at provisioning, guest experience software more times than any GM who works in any hotel. They’ve become the expert because they have seen this decision being made. Let’s call it eight times a week. You know, I’ve been market product that’s probably less than 10 grand, they’ve probably see this a few times a week, at least, right? Like, let’s get, let’s say eight or 10 times a week, right? So three weeks in, you’ve talked to 30 people who are at that same crux of decision on what they’re doing for guest experience software. And now you talk to a GM and you go, please, sir, can you consider the demo like you’re begging for it? Because you’re a new rep, you probably haven’t seen that first cheque yet. But truthfully, you’ve got enough of a pattern to be able to say, this is the trend. GMs on the cutting edge are doing this, GMs that are laggards that are waiting are doing this, they’re all looking at this and thinking, Okay, it’s too expensive, or it’s too desperate to that. You’re actually more of an expert as a sales rep than almost anybody else in the field. Yeah, sure. There are some people who are really true experts that built the technology wrote about it grad school, and now they’re running software companies. So yeah, you probably not going to like win a fight with a CTO, right? But if your buyer is not the CTO, or CTO is the buyer, but they’re buying something specific, you actually know a lot that you may or may not give yourself credit for. Right? So let’s go back to Megan. Right. Megan is selling into e commerce fashion brands in the UK. This is probably the year 2012. And she’s absolutely crushing it. And any one of those clients who would say to her, Hey, what is everybody else doing? She’s got a really strong opinion on what the best ecommerce fashion brands in 2012 are doing to get their handbags to the world from one specific market. She knows how they’re advertising, she knows what their other strategies are. And because she also likes that space, you can talk about what the designs are like and what makes them cool, what type of leathers are using etc. I don’t know that space you know, I don’t know anything about it. But if that’s the space that you’re passionate about, then Wow. So for anybody listening who’s on the sales rep side, as opposed to the founder side on the market, if you’re on the sales rep side, let’s go make sure you sell something in an area where you prospect by default. If you read guns and ammo magazine, you should probably go work for Sigur Glock. If you like to sit around and read, you know, Mother Jones, and you like to think about like how communities are managed and what cool opportunities are on local middle school and you’ve got on the PTA because you care so much about education, well, let’s go sell for K 12. And actually make that sales process better or I don’t know maybe, you know, companies like zoom or other people who have kind of had to pivot towards education during the pandemic, they’ve got a need for somebody who’s going to default and think about that space. You know, the guns and ammo reference is from a friend that I knew who was absolutely passionate about this space, and couldn’t figure out where to use his skill set. You know, regardless of how you feel about people who have that hobby, you know, he went and sold on behalf of a manufacturer into police departments, and is now every day is his perfect day. He absolutely loves his job, he loves the conversations he has the same way that you know, in 2012, somebody who’s selling you know, the handbag market in the UK is probably pretty thrilled about the type of fashion that’s coming out of the UK at that time. You know, it’s just a matter of finding those things, and then the pattern is going to match on its own. Just don’t forget, you’re an expert.
Walter: So what are those medic questions that a rep, a founder, even yourself, right, you went through and had as many questions? What are some of those for you?
Ryan: For me, I go back to when I talk to folks who are making a transition in their career. I asked them what they like about their day, what their best day had, what their worst day had. You know, I was recently in a coaching call with a director of sales at a big, you know, tech company that all of us know about. And we were talking through the things that make the day really good. You know, and some of his things were knowing that the meeting connects the purpose, and specifically where the purpose has to do with the team career management conversations. Okay, well, once you know that you like career management conversations, you can start to prioritize that on a grid. One of the product managers I worked with years ago, left to became a VC. They did what every young sales leader wants to have happen in a situation like that. He got his VC, wrote a cheque into a company turned around and called me and said, hey, these guys need a head of sales. You want your big break your shot? I said absolutely. So I went over I did a couple interviews. I got really excited about the company. And if you know me well, and you’ve heard my stories or listen to me on other podcasts, you know that I can’t go full hour without talking about my wife Jenny, who helped me make a lot of my career choices. So I come home from that meeting, the founder’s name is this guy named Alex. And he was building a really cool like analytics software over the gaming space. He had been a rising star engineer at EA or one of the other big game houses. And so he had built this cool analytics tool, and he had somebody go sell it. And so I came home. And I said, Jenny, this is what the job looks like. The job description, it’s a head of sales job with no sales people that work there. So my job is to go close the first 20 customers, try to get to a million dollars AR and then build the team. Now those are kind of magic numbers in software startups, right, especially at SAS. You get to a million bucks, and then you can start to build the team, because that’s really probably when the founder is going to raise series A, that use of proceeds from that four or five, maybe $10 million round is going to go into, you know, spend a million dollars on hiring a sales team. That’s not that crazy, you know, 10 people 100 k basis or whatever. And you’re off to the races with a million, 2 million dollar sales team from that race. And I lay this all out, she goes that sounds great. Except you don’t like to sell. You like to manage, you like career development, you like people. And how are you going to be able to get through this next year where you’re doing nothing but selling in a vacuum without a lot of people around with a busy CEO who can only come to some of your calls. And her point was like, you might not make it out of that kind of like that initial phase. I didn’t end up pursuing it. And I realized that it wasn’t a good fit. You know, that was the biggest reason, there are a couple of things that were quite right about that opportunity. But it changed the way that I looked at other jobs. And so I focus my effort on how to go create my perfect day at the job I had, which was, you know, the first sales manager that Ron that I built out that the number one big market team and later SDR and sales operations before we call it, I built that team up and then spun it off to the VP of ops. And I had a great time doing that for at least another maybe a year and a half after that first fork in the road, before starting to interview for VP of Sales jobs, knowing that I needed to be in a sales management. So I only looked at companies that already had at least five employees and sales, because then I could also evaluate the opportunity based on will my secret sauce, my special like, my magic skill is training. You know I started my career as an educator, I love to train, I love to talk, I love to mentor, love to coach. And because that’s my special skill, I need to find a role where there’s a team who needs that, where it’s one of my closest friends, the guy got me into sales was actually somebody who, you know, I don’t think is somebody who, yeah, he’s managed teams. But I think his skill is being able to sell anything, you know, these guys, right? You’ve got products like this, who could sell anything. I always make the number and sell anything. Well, you know, that person is going to evaluate that first time VP of sales in A series a pre-series a company a lot differently. They’re going to say, Oh, well actually, let me not go somewhere with a team, let me go somewhere where I don’t have to worry about whether or not Jimmy or Jeanine is taking time off today. Or I don’t have to worry about anything more than maybe one or two SDRs who are going to keep my pipeline full. And instead I can worry about who I’m going to close. And I’m going to go do that first million dollar deal. Or I’m going to do that first breakout enterprise deal, or I’m going to go like the friend I was telling you about who’s done billion dollar deals like, okay, somebody who’s worked on a billion dollar, multiyear deal, who understands what it takes to move out of the, you know, senior buyer is responsible for 100 million bucks to get to that person to go 10x that. Like you’re bringing all senior leaders into an operation.
Ryan: On an investment like that. And so that’s an org change project. That’s project management. Right? And I used to think like, why would you get an MBA and then go into sales? That doesn’t make sense. Sales are for people that don’t have graduate degrees? Well, sure enough, and then you start to see sales, it means a lot of different things to a lot of different people know.
Walter: And that’s, I think, what’s really interesting about sales. It’s not black or white, it’s like Shades of Grey. Well, I think it’s really interesting, if you think about this conversation is, in the beginning was as a founder, who are you going to hire and think about what they can do for your organization, like, what is it you’re selling? And then in reverse, asking yourself what are those questions and being able to ask those type of questions of what is your greatest day? Like, what does your best day of work look like, right? And you know, complementing those solutions.
Ryan: If you can answer that stuff for yourself, I think you’re going to be able to optimize for the right experience. And then if you’re interviewing somebody, how do you answer that in an interview? If you ask somebody what their perfect day is, they’re gonna say everything they read about on the job description.
Ryan: But if instead you can figure out what they liked or didn’t like about their last job. You know, I was just talking to a VC who asked me about one of my early experiences and he asked why that the company I was telling about wasn’t completely successful. And then I realized he was interviewing me, because he wanted to hear what my assessment was on the opportunity to find out if I was consistent with the way he thinks about his opportunities before he has me mentor and develop companies in his portfolio. And I realized, oh, that’s a really interesting way to say it. you know in that role, my mentor was Suresh Khanna, who is the director of sales for Google’s North America team before he took Adderall from about probably about eight or 10 million to 300 million or whatever the, you know, their published number was. I won’t speak out of school on that. But they were doing $750,000 a day, the day I left, right. So Suresh you know, really grew that team. Well, what was interesting about working for Suresh is he had this way of asking people he had been in kind of private. Well, I think you’d probably call it more like investment banking. But he does some BD stuff, and some investment banking stuff. And so he had talked to people about a lot of different types of businesses. And so he’d asked a sales rep, who maybe were at Morake for six months and say, tell me about how Morake makes money. Super open at it. Tell me about how they make money to hear what was interesting to the person that you start to get, you know, perfect day is one way to ask it. But asking how that company makes money is also going to reveal my bias of the things that are important to me. Oh, we make money by selling the shopping malls. Okay, well, then that means you’re in one segment, you know, or you understand a problem, we make money by selling to this IT problem. Or we make money because we like recurring subscriptions. Well, okay, then I know you’re interested in SAS, you’re interested in the way the SAS business model works. Which makes sense if you’re talking to somebody in Morake, great. He asked that question as somebody who sold solar panels, who was part of like a three part channel distribution chain.
Ryan: And went off the rails like this poor guy. He was like, can I get a marker and he went to the whiteboard and tried to explain it. And then he came back a week later to do it right because he’d been thinking about it all week, he ended up getting the job and he was great. I loved working with him. But it took him a while to get out of that hole. Because he was in a really complicated business, and opposed to saying, hey, look, I don’t know, but this is the thing that I do really well.
Ryan: That probably would have been a better answer for him.
Walter: Right. No, absolutely. Well, last question Ryan, what’s a message that you want to leave with people who are listening to this?
Ryan: I think it’s really easy especially right now to feel like other things, people, events control you. And I just don’t believe that’s true. And I don’t think it’s one of those booths trappy everybody can do anything they want. There’s a lot of limitations. There’s a lot of bias in this world, there’s a lot of things that are really hard to accomplish based on how the deck has been stacked against you or stacked for you. But I will say that if you approach your challenges with an openness to outcome, and knowing, hey, if I go do this experiment, this is the thing that comes out of it. Or if I go try this startup, even if it doesn’t work here, the things I’m going to learn, or in the case of the sales rep who goes out to that new job, it may not be an equity win. But you’re excited they offered you equity, but instead think about okay, what am I going to learn from this experience in a year? Right in the store, I didn’t tell you, which is what I usually tell about Jenny is that when I got to Admiral, Google just released remarketing. Probably two weeks after I got to Admiral and so I came home and said, hey, to this girl I just moved in with I can’t pay rent. And by the way, Google released the same product of this startup that I just joined. So I’m effed. Financially, I can’t do anything. Her answer was, if you’re going to learn something, you should stay there for at least six months, and I’ll pay rent. Because she knew the value of learning, we both had this experience as educators. And so she knew that that was valuable. She knew that was something that was valuable to me. And I was fired up about what I was learning about the ad tech ecosystems, right? So I was like, well, okay, that makes sense. And then, you know, of course, you know, I’m not gonna let her out of my life, or ever move out. So I stayed. You know, it’s been over 10 years now, but that experience was pretty amazing. But it also changed my calibration and my compass to be what am I gonna learn from this experience? I’m not looking at; am I going to make my number this year? And how much do I make? You know, a lot of junior salespeople they get their plan or their offer letter and that comes to the comp plan or they’ve talked to another rep there and they start trying to figure out the great sales reps do this all the time. But start to figure out, okay, here’s what if I do X, Y and Z, here’s what I’ll make. As a VP of Sales I evaluated an opportunity based on if I can show up in four x where the company is today, in the next 18 months, as a baseline worst case scenario, if I think I can get into four x in 18 months, that I know that I’m still on the trajectory. I’ve been there more than a year and a half, I’ve been able to ramp up by the first six months, I was able to actually do the job for a year, learn a lot from that, I’ll get a lot of experience, it won’t be a blemish on the resume even though a bunch of VPS of sales get fired every year for doing their jobs with companies that aren’t ready. Can I go out and do that and have you know, four x growth? More than that is great. That’s the cherry on top. Everybody thinks you’re the most amazing thing since sliced bread. But if I think I can, Okay, can I go and four x. If I can do that in a way where I know I’m going to learn the thing I wanted to learn, like how a company goes from series A to Series B, how the fundraising happens. If I can use this as an opportunity to get into rooms I wasn’t able to get into before, whether that board meetings, or whether that’s who you’re interviewing and who you’re hiring, who you’re managing, getting to a place where you’re at a team big enough you can actually hire people smarter than you, which is really hard to do if you’re a startup of two or four people but it gets a little easier once the company gets bigger people see that you’ve got some success. And the people who used to be your bosses are coming to you looking for jobs, that’s an amazing thing. There’s a lot to learn from that. And so I think that all of us are in an opportunity where that kind of learning is in reach. But we have to be open to seeking it out.
Walter: Amazing. Ryan, as always, it’s a great conversation. Thank you so much.
Ryan: Thanks for having me.
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