Dan Chapman – Former VP GTM at Full Story & Bento

Speaker 1 00:00:02 Welcome to the Growth Elevated Leadership podcast with Julian Castelli. Each week, we talk with senior tech leaders to explore stories and insights about the challenges involved with growing technology companies. We hope that these stories can help you become a better leader and help you navigate your own growth journey.
Speaker 2 00:00:29 Hello, this is Julian Castelli. I’m the host of the Growth Elevated Leadership podcast, where each week I talk with inspirational entrepreneurs and leaders in the tech industry. past guests have included CEOs and CXOs of great companies like Work Front, CG healthcare, Radical Systems, in Moment, Vox, Pop me, the San Francisco 40 Niners, and many more. this episode is brought to you by Growth Elevated. Growth elevated is a community of tech CEOs and founders and CXOs who are committed to working together to share best practices and learnings in an effort to become better leaders. We do this through educational events and programs like this podcast, and we also have an annual summit in beautiful Park City, Utah. So if you like skiing and you like talking tech, you like talking growth.
Speaker 2 00:01:20 check us out at Growth elevated.com. Today I am excited to have a conversation with Dan Chapman. Dan is a go to market advisor and fractional CRO, and he focuses on very early stage B2B SaaS companies. He focuses on founder led sales and that whole topic of how do you go from founder sales to scaling sales? Dan learned to sell as an executive at Google, and then he put those skills to work at Bento Box and Click dimensions. Today, Dan helps technical founders from selling their first customers to hiring the team and setting the stage for scale. His unique background across multiple go to market roles, and a hands on approach helps founders navigate the critical inflection points that often derail startups in early days. Please welcome Dan. Hey.
Speaker 3 00:02:11 Thanks, Julie. Glad to be here.
Speaker 2 00:02:13 Yeah. Glad, glad, glad to, have you here today, Dan. You know, the the topic that, you really focus on is, is, is really critical, right? Because so many people, the innovation economy is fantastic.
Speaker 2 00:02:27 We have people coming in from all kinds of areas. They come from a domain problem that they see, they want to solve. Some come from technology and then they’re faced with this challenge of sales. Right. And so having someone like you that can help move from founder lead sales to scale is critical. And I’m looking forward to talking about that. Before we do, though, give me tell us a little bit about your your background. How did you get to become an expert on early stage tech sales, and how did your background lead you to choose this as as your passion?
Speaker 3 00:02:57 Yeah, well, I’d say, my background is a little different than a lot of other folks here. in this type of role, doing this type of work. And that actually started out as a technical founder myself, as a software developer, started a small dev shop and kind of learned the hard way, how to sell by making pretty much every mistake in the book. I didn’t so much cut my teeth learning to sell as like, knock my own teeth out, running into the wall over and over again.
Speaker 3 00:03:25 and so as I kind of matured in my career and shifted my focus more towards go to market leadership roles with later stage and growth stage tech companies, I really came to appreciate just how hard it is as a founder, especially if you’re coming from a technical background, to really be successful in those early days of getting your go to market launched. And so what I wanted to do is make that process easier for other founders and kind of give back in that way.
Speaker 2 00:03:51 That’s fantastic. And so you started out with some software. You also have some experience in leadership and strategy with both the military and McKinsey. Tell us a little bit about how that and how that shaped your journey.
Speaker 3 00:04:03 Yeah. So I actually started out in software development, and then I went to undergrad and to pay for undergrad I did ROTC, so I spent five years, almost five years as an infantry officer in the US Army, including some time overseas. And, you know, couldn’t imagine two more different chapter one and chapter two kind of stages of a career, but really great experience, really formative for me, helped me understand the messier human side of organizations and just how important it is to really have a mission and drive clear intent even in, you know, high stress, rapidly changing environments.
Speaker 3 00:04:45 And I think some of that experience is actually why I gravitate towards earlier stage and what can often be, you know, the messy and chaotic world of startups.
Speaker 2 00:04:55 I got it. And then. So then after that, you you you went to McKinsey for a little while, and then you worked at Google as well.
Speaker 3 00:05:03 That’s right. Yeah. So, you know, coming out of the military, you know, wanted to explore and kind of broaden my horizons a little bit. So did the thing that a lot of people do when they don’t know what they want to do next and went back to school, did an MBA and then joined McKinsey as a strategy consultant after that. I spent my first year as a generalist, and then in my second year, I really focused on on tech. That’s kind of what I was. I was drawn to, and then, left to go work at Google, where and I managed to kind of weasel my way into working with the corp dev team there, working with, startups that Google had acquired.
Speaker 3 00:05:42 But they were keeping as kind of standalone brands or entities. and that’s where I got to work with founders again. and so that’s really what gave me the push to go back to startups. And so I left Google and started doing that full time and spent, Did three different, roles with three different startups as a, as a go to market executive. over time was really fortunate that of those three teams, two of them exited another one. became a unicorn. and so I got to work with some very high quality teams, some great products. and got some, some amazing experiences along the way.
Speaker 2 00:06:17 That’s interesting. So when you’re at Google. You’re you’re required by Google. Do they do. I’m not sure. There’s a lot of variety, but the companies you worked with were they fairly stand alone. And were you kind of an advisor from Google and what were you helping them with?
Speaker 3 00:06:30 Yeah. That’s right. So, a lot of it was, figuring out from a go to market strategy perspective how to leverage the big distribution advantage that that Google could provide, because a lot of these startups had relatively nascent, you know, revenues, or, you know, distribution, especially relative to, you know, the massive sales organizations that the ads team or that YouTube had.
Speaker 3 00:06:53 So it’s like, how do we get plugged into those organizations? And then, you know, all the way down to some of the basics around, like, just how do we think about go to market, how do we think about, measuring what’s working and what’s not, those types of things.
Speaker 2 00:07:06 Oh, that’s sounds like a great, great experience. And so what what pushed you to kind of say, all right, now I want to go out and do this as an advisor.
Speaker 3 00:07:15 Yeah. So after my last full time role, I worked at the public company that acquired the last startup where I was CEO and head of sales. and I really enjoyed that experience. I kind of had the itch to go back to to earlier stage. And, you know, I spent some time reflecting and, and a lot of the lessons that I learned from kind of growth stage like series A, series B, series C, I realized some of those had, you know, those problems that we were working on.
Speaker 3 00:07:45 We could have made it easier on ourselves by starting earlier and setting the stage correctly from the beginning, as opposed to having to go back and kind of fix some of that stuff while we were scaling. and so I just kept getting pulled earlier and earlier, with the, the work that I was doing with clients. And I wanted to try going out on my own and, you know, seeing if I could create value in, by myself. So just took the leap, took the chance and, haven’t looked back.
Speaker 2 00:08:12 Well, fantastic. Let’s talk about some of the things you do with early stage founders. You know, one of the concepts you talked to me about was selling to learn versus selling to scale. What does that mean? And what what stage is that?
Speaker 3 00:08:27 Yeah. So a lot of founders, when they’re they come to me, they’re looking for help setting, a scalable foundation for go to market. And while I think that’s an admirable goal, oftentimes those founders, when I dig in, are actually in a different stage.
Speaker 3 00:08:43 They’re not ready to scale yet. They need to really refine they’re messaging their positioning, and even sometimes what the product does for their prospective customers. and in some of the, some cases, we’ve got customers who really don’t have much beyond a few design partners. And so they need to go and validate that what they are building will sell. and so I think of that as when you’re in the founder led sales mode, you should be really thinking about your objective is not creating scalable processes and playbooks, but rather learning and using that chance to optimize the fit between what you’re building and what the market needs.
Speaker 2 00:09:23 So we’re talking you know, we’re talking about product market fit. That is one of the most used and least understood, terms in early stage startups. What’s your definition for product market fit?
Speaker 3 00:09:37 Yeah. So I think there’s a couple components. and there’s a lot of people who’ve written much more detailed, you know, a perspectives on product market fit. And so I’m not going to try to, you know, rewrite all that.
Speaker 3 00:09:51 but I think the selling to learn phase is really about proving traction and, consistency, meaning that you’re actually able to sell your product and that that your customers, your early customers are using it and seeing value in the same way. That’s the selling to learn phase. And then I think to get to product market fit, you really also need to start to get into the selling to scale phase, which is that you need to prove that somebody that’s not the founder can sell this and that. You can actually you have some positive unit economics, meaning that the expected kind of post-acquisition value of a customer is greater than what it cost you to go and acquire a customer. and then the last piece of this is momentum, which is, you know, I’ve seen people talk about, you know, this is measuring like your inbound demand or the number of active deals that you’re working, but something like that, just depending on your go to market motion, needs to be compounding and accelerating over time to really feel like you have good product market fit.
Speaker 2 00:10:56 Terrific. So you’re you’re selling the learn. You’re you’re you’re figuring out what the problem you’re solving is. Do you have like a template for, for founders that you use to kind of like you find that they’re not organized enough and documenting what they’re learning. And how do you help them really crystallize that first stage?
Speaker 4 00:11:15 Yeah, it’s a good point.
Speaker 3 00:11:16 And and the key in what you just said is really writing things down and documenting it and then iterating over time. And, often founders are so busy, they wear many hats. And even if you’re in a team of 2 or 3 co-founders, often whoever is responsible for taking the product to market and doing selling is that’s not the only thing they’re responsible for. But I think, you know, of the activities that you can do, as a founder, writing down your process and building your own. You know, whether it’s like a one pager or a script, if you want. Some of that feels a little bit like too heavy. But, you know, doing the basics on that and then making sure you are reviewing your own calls and learning from them, each one like you is a is an opportunity.
Speaker 3 00:12:05 Don’t waste it. make sure you’re testing something out that’s very deliberate. And then when you find traction, make sure you’re repeating those things that work and discarding the things that don’t. Trying something else that’s new. That process, I’ve seen really help founders accelerate, especially with those first, you know, 10 to 20, conversations that they have with with new prospective customers. Those are really precious. And so you need to make sure you’re extracting as much value as possible out of that. so yes, I have some templates. but a lot of it is honestly just the forcing function of having a, you know, regular cadence with founders to go through this process and make sure that we are deliberate, about learning from from each and every conversation we have with prospective customers.
Speaker 2 00:12:50 Got it. Okay. So you’re working with founders. They’ve gotten their few initial sales. And, you know, they they’ve documented it based on some of the help that you’ve provided. So how do they make that bridge to non founder sales.
Speaker 2 00:13:05 That that’s a big one. And it’s really hard. But new people come in right. Because I think you and I talked previously as a founder you have this magic superpower right. You know the problem. You were passionate enough about the problem to start this business. You’ve you’ve built the product. You’re probably in love with the product, which has pros and cons. You’ve talked to customers, you can tell stories, but then you bring someone in who’s just knew. My goodness, that’s a that’s a giant chasm, right?
Speaker 3 00:13:32 Yeah, absolutely. And before I answer your question, there’s one other thing to that. That’s a bit of the founder sells magic, which is you can actually change the product, which hopefully.
Speaker 5 00:13:43 Hopefully, you know, so you have that that’s.
Speaker 2 00:13:45 Additional superpower.
Speaker 3 00:13:48 Yeah. Now if you’re if your first salespeople are also promising things and adding to your roadmap, maybe you actually haven’t solved for that one key part of the selling to learn, which is consistency. and so, you know, I’d say one, I think founders often bias towards wanting to bring somebody in, either as a full time sales person, or even sometimes as a, as an early sales leader.
Speaker 3 00:14:13 to early, I would say this selling to learn stages is really precious time. And being fully in control of the go to market is something that will only happen once. And so I would say make sure you really nail the criteria around selling to learn, which is that you’re actually getting people to pay for your product, not design partners, not, you know, 90% reduced rate below what you hope to be able to sell the product for. But like you’re actually selling your product and that you’re seeing consistency in both who you’re selling to. So like, what are my customers look like? You know, do I do I act? Can I take my early customer set and create an ICP from it pretty clearly as well as are they all using it the same way? One of the other things that’s.
Speaker 5 00:14:59 Selling it.
Speaker 2 00:15:01 To a consistent customer who’s using it the consistent way and probably, you know, getting getting consistent value that you can build upon. So those those four of the pillars. That’s right.
Speaker 5 00:15:12 Yeah.
Speaker 3 00:15:13 And and I think the, the other piece like that we often see in early founder led selling is there’s especially for technical founders who come who really know the problem well. They’re often adding in whether it’s like an explicitly a line item. They’re adding in services to right to make the product work. And it goes sometimes beyond onboarding. But, you know, continuing to to maintain the product, or to help build other processes to make sure that product plugs in. And that’s in particular for like mid, upper mid market and enterprise sales. but and that’s okay. I think you just want to really make sure that you’re not having to pivot too heavily in what each customer’s implementation of your product looks like, too. and it’s fine at the beginning. Explorer.
Speaker 5 00:16:00 Sure. But yeah, like, you want to pick the one that seems to be having a.
Speaker 2 00:16:03 Services enabled product. again, it’s a it’s a superpower, but also could be a challenge in terms of having tight product that’s repeatable. Right.
Speaker 2 00:16:11 And you know, when you talk about lifetime value in scale, that’s probably where you start seeing the impact of some of that customization versus you consistency, which I know is one of your tenets there.
Speaker 5 00:16:22 Yeah, absolutely.
Speaker 2 00:16:24 Okay. So you’ve done that. You’ve worked with the founder. They’ve done the discovery. They’ve done the learning. And now is that scary point. Like, I have to do something beyond myself. I have to scale. And, I think I wrote a blog way back when, you know, based on, you know, one of my founder experiences like, don’t we just need to hire salespeople? We just go hire salespeople or what’s the next step?
Speaker 5 00:16:48 Yeah.
Speaker 3 00:16:50 I mean, I think that that can be right. I’ve seen, you know, I think people consider one of three paths. Usually they’re either looking to bring on an SDR because the primary problem is actually about lead generation. And the founder still wants to run those early conversations. But what they need help with is, is creating demand.
Speaker 3 00:17:08 And that can be successful, especially if it’s a very technical product. And it would take a while to hand off, to somebody that can run a full sale cycle and close. the second is they want to bring in 1 or 2. I think it’s really common and popular nowadays to bring in two A’s. I think the idea there being that if you hire two at the same time, you can validate if it’s not working well, whether you know, it’s more about the person and the fit for the background that that person has and the role and the need. or whether it’s just not ready to be handed off yet. and then the third option is bringing in somebody who will be, a sales leader, or, you know, go to market leader that, you know, usually has seen this before and is ready to go back and do another lap starting at zero. But but takes more of an IC role at the beginning. I think that that is the third one is it’s really rare to find somebody who has truly done 0 to 10 million or something like that, and wants to take another lap.
Speaker 3 00:18:09 I think the most I’ve ever seen somebody do is two times. Yeah. it’s.
Speaker 5 00:18:13 Pretty exhausting, right?
Speaker 3 00:18:15 It’s extremely exhausting.
Speaker 5 00:18:17 Let’s go back.
Speaker 2 00:18:18 And, you know, I was saying that the hiring salespeople almost ingest because, like, I learned the hard way that, you know, maybe it’s not the last thing you should do, but someone, you know, a good sales expert said that’s the last thing you should do. And his point was, you hire salespeople and you haven’t documented all the things you’ve learned And put them into a positioning framework and maybe have a sales deck and all the things that you talked about earlier. If you haven’t taken those and turn them into something that you can train someone with. It’s really going to be difficult for those salespeople because they’re not just coming in and selling to their friends, right?
Speaker 3 00:18:49 That’s right. Yeah. I mean, I think, what we talked about earlier, which was the even when you are in that selling to learn phase and you’re iterating and experimenting and you’re changing what you do from call to call, you’re talking about writing it down and building a playbook.
Speaker 3 00:19:06 But that’s not the stage where you should be handing it off. When you can reuse the same playbook and you’re not having to change it every time. That’s when I think that’s a requirement for sure.
Speaker 5 00:19:17 Yeah, because now.
Speaker 2 00:19:18 You have something you can train someone with, right? That’s right. I suspect you’ve seen several examples of salespeople coming in and not having that training and surprise there. You know, not only are they not the founder, but they haven’t had the training and therefore they don’t get the benefit of that cell to learn cycle.
Speaker 3 00:19:36 That’s right. And look in a you know, in a pinch you can it is much more time intensive as a founder, but you can run those conversations and those processes side by side with your first aid, but then you’re just putting the burden of the work on them to create the playbook. I’ve seen it, you know, work better when it’s the founder doing that work with, you know, an advisor or somebody else that knows what playbook building looks like.
Speaker 3 00:20:02 and then the your first day, he walks into something with a much better chance of being able to successfully ramp, especially in those first, you know, 30 to 60 days where it’s critical to.
Speaker 5 00:20:12 Get a key.
Speaker 2 00:20:13 Element of of, you know, you’re offering do you help them build that, that, that toolkit, that, that playbook and what what are the chapters in that playbook?
Speaker 4 00:20:22 Yeah.
Speaker 3 00:20:23 So I mean, the really it depends on the selling process. For more transactional sales, you might need kind of like a one call closed script where you walk through everything from qualification and doing a mini demo of the product to position, you know, presenting pricing and then closing for, you know, enterprise sales cycles. It’s obviously much more drawn out. And you’ve got to have actually a series of playbooks around. Here’s how we run qualification and discovery calls. Here’s how we run demo and scoping calls. You know, here’s how we run our validation events. And then, you know, here’s how we run through the procurement process, legal and, you know, compliance and all those types of things.
Speaker 3 00:21:05 So it really does need to be fit to the market.
Speaker 2 00:21:09 The latter is an enterprise sales motion. The former is is much more of a, you know, SMB or that’s right. Higher, higher volume sales process. But you know, but but if you’re not a, a trained sales professional, you probably don’t have those playbooks lying around that you can just roll out.
Speaker 3 00:21:26 You know, and in fact, like there’s often you may be forgetting to do things like, hey, I’m running a sales, hoping to run a sales cycle, and eventually sell this product for hundreds of thousands of dollars. I need to have a, validation event or, you know, I need to to learn how to do a proof of concept, like some of those things. you know, just a founder may not be aware that that’s that’s generally how those that type of customer buys. So, yeah, a lot of these are just based off of best practice. And then we go from very early like first principles of, you know, how does this product need to be sold.
Speaker 3 00:22:03 And then we’re testing those over time and they’re kind of evolving. and then yeah, eventually your, your, your early sales people and your early sales later they’re going to create a different version of the playbook that doesn’t allow for founder magic. That’s a lot more detailed. that has, you know, some of the materials from your marketing, what your marketing team will eventually create around case studies in those types of things.
Speaker 5 00:22:25 Right.
Speaker 2 00:22:25 What are your thoughts on when to hire the sales leader?
Speaker 3 00:22:29 So I, I think it needs to be when you have pretty significant traction and multiple salespeople that are hitting and hopefully exceeding quota and ramping quickly. one of the challenges with hiring really good, like a VP of sales or VP of growth, as a startup, is that you’re asking somebody to take a pretty significant risk with their career. they tend to come from, you know, they tend to have done well and gotten with a company to series B, series C or beyond. And so the ones that you want are going to really rigorously do their diligence around the momentum that the company already has.
Speaker 3 00:23:10 and so you want to make sure that you have that like it’s I’ve worked with clients where we went out too early and just the caliber of candidates that responded to, you know, our posting was very different, even just three months later, because of how much more momentum we’ve been able to build and the, you know, the proof that we were succeeding in the market, and retaining customers and expanding customers, that type of thing. as well as just, you know, what’s your, your what’s your, you know, size of your company as a starting point, most of these, high quality VP’s are going to want to walk into a team of at least four A’s, all of whom are doing well, so that they can just build on something that’s successful.
Speaker 2 00:23:53 Awesome, awesome. That that makes that makes good sense. Terrific. So. So tell me where people can find you.
Speaker 3 00:24:05 well, feel free to visit my website, Dan Chapman. Com I’ve got a link there where you can book time with me, if that’s, something you’d like to chat about in more detail.
Speaker 3 00:24:16 I’m also just Dan at Dan chapman.com. If you want to shoot me an email and you can find me on LinkedIn, I’d be happy to connect. I need to be better about, about sharing some of these thoughts a little bit more consistently, consistently. but I’m planning to to start doing that soon. So look for for more content for me coming to.
Speaker 5 00:24:34 Well that’s.
Speaker 2 00:24:34 Terrific. And, anyone you want to shout out that the, that helped you, helped you, get to where you are now?
Speaker 3 00:24:42 Yeah, absolutely. I mean, there’s too many to name individually, but, to all the founders and investors who believed in me when I was just starting out and getting back into startups, you know, coming out of big tech, Google and all that. to the teams I’ve been honored to lead who make the job just so rewarding. and the, you know, the founders who trust me now as an advisor and a fractional CRO, I’m truly grateful for the chance to get to help people out along the journey.
Speaker 2 00:25:10 Hey, another another thing we like to do is share some, you know, obviously people can come talk to you specifically, but I know you’ve got some. You like your your reader and you’ve got some books that you think are really valuable on this topic. What would you recommend if people want to start out by just reading reading up on the topic.
Speaker 3 00:25:25 Yeah. I mean, look, if you’re starting from zero, there’s a lot of good, like classic sales books. I’ll talk about one that is relatively newer and that I’ve really enjoyed. And, you know, kind of like put some of the principles to use with my clients, which is the jolt effect. It’s a, really about, it’s a follow up to kind of the challenger sale. and it’s a great newer one. If you’re struggling to get buyers to commit to changing and understanding what it takes. like if you’ve got prospects who understand that what their, you know, their current approach isn’t working, they understand the value that’s on the table, but they’re there’s something that’s holding them back,
Speaker 5 00:26:06 Or taking the plunge stick.
Speaker 2 00:26:09 Which is get things moving. That’s a good, good word for it.
Speaker 5 00:26:14 Yeah, it’s a great book.
Speaker 3 00:26:15 And, you know, we don’t have time to go into all the principles. but, you know, I’ve spent some time with my teams kind of going over some of those. And it’s a very practical book. It’s not just theoretical like you can put those lessons to use right away. I’m also a big fan of not just sales books, but kind of broader business, reads. And I really liked, The Outsiders, which is about, you know, it’s like a series of stories about unconventional CEOs and how they approached, you know, their business and created, outlier type results. a classic book on strategy, is good strategy, bad strategy. And then there’s one, called the Success Equation, which is it’s a bit of a humbling read because it’s, it talks about understanding the impact that luck and randomness have had on have on success and, and even, you know, how to quantify that.
Speaker 3 00:27:12 And I think it’s something that, frankly, those of us in the world of venture, you know, should keep in mind, when we when we think about what we’ve done in the past, and maybe that, you know, it’s not just about us being great, but a little bit of luck involved too.
Speaker 2 00:27:25 Of course there is. That sounds great. I’m going to I’m going to write those down and check them out. Dan, this has been great. Great great topic. I wish you best of luck. And I’m sure that your your clients are happy to work with you and really dive into this. There’s nothing more important than early sales, early stage sales, traction. And I love your focus on it and look forward to continuing our conversation. Thanks for joining us this morning.
Speaker 3 00:27:49 Yeah. Thanks, Julian.
Speaker 1 00:27:54 Thank you for listening to the Growth Elevated Leadership podcast. If you enjoyed this episode, would you please follow us and subscribe on your favorite podcast player and we’d be grateful if you recommend it to a friend.
Speaker 1 00:28:05 If you’d like more resources on how to become a better leader in business, we invite you to visit us at Growth elevated.com. We’ll be back next week with more insight from another great tech leader. Thank you.