Zero to $1M: Founder-Led Sales Is the First GTM System

Machine-generated transcript from the episode video, cleaned for punctuation and names. Speaker labels are not included.

[0:05] In this episode of the GTM Vault Podcast, we sit down with Anna Levya, a dynamic early stage VC and B2B sales leader currently at Pear VC. Anna brings a unique blend of experience from both startup and enterprise environments. Join us as Anna shares her journey, her approach to developing GTM strategies, and the unique challenges and opportunities in the startup ecosystem. Without further ado, I want to get right into it. Anna, you have an impressive background in both founding startups and leading sales teams. Can you share some of the pivotal moments in your career that led you to your current role at Pear? Yeah, thanks so much, Rick, for having me, and happy to share. You'll have to bear with me a bit with giving context. I think the context that I'll share about what led me to this role will be helpful as we go through this entire interview. So as I look at my life, there are really four things that I'd say have led me to this moment and shaped who I am as an entrepreneur and as a supporter and

[1:09] adviser to entrepreneurs. First, it's being a daughter of immigrants and growing up with parents who worked multiple and attempted and ran multiple businesses, and just seeing their entrepreneurial spirit really shaped me and made me someone who was always looking for opportunity. And second is my decision to get into sales. I was the first person in my family to go to college, and I think as an immigrant kid and being the first, there was a lot of pressure to go to some of the most popular professions, which are law, medicine, or engineering. And I ended up going to my dream school, Princeton, and once there, really wasn't sure career to pursue. I thought I wanted to be a lawyer, and so did everything kind of on to get to that path. And then when I graduated, realized that my motivations for pursuing law were great. And so I started having conversations with mentors and alumni and asking them, what should I do? These are my interests, this is what I'm good at. And repeatedly, folks kept saying, you should get into sales. And it was almost offensive to me. I had, like many people, a misconception

[2:12] of what sales people do, and you think of used car salesmen, and it just, to me, from the outside, not having ever done it, not being close to tech sales, felt like unintellectual. And so I wasn't, again, was almost offended when people would say, you should get in a sales. It came up enough from enough conversations, I said, this is really merit something. And the heart of the advice was, if you're going to work in tech, you either want to be in product, or at like building the product, or selling the product. Those are the most impactful roles to have. And so I started spending time on the sales floor. I was at Box, on the revenue side, on the finance team, and I started just hanging out with salespeople, shadowing them, really trying to figure out what they did. And I realized, wow, is an exciting job. It's, you're always learning, which is aligned very well to me. I was kind of a nerd who was constantly wanting to be challenged, and sales is very much that. You're solving problems for end users. If you're really good at sales, you're really becoming a strategic partner and a problem solver, and that again aligned very well with me. And the best sales people are thoughtful, and they want to listen, and they want to

[3:14] connect and build relationships. So all of those things really did align well, and I realized all the advice I'd been given was right. And so that first decision to pivot into sales, I think, was huge, and of course has set me up on this course. And then the next big pivotal moment, I'd say, for me was deciding to go to business school. So many people, if you are familiar with sales, know that in order to go all the way up to the highest ranks of sales, you really don't need an MBA. It's one of the few professions where just getting experience from the ground up is what's required. So there's no like necessary, no need to get an MBA, and it's almost even looked down upon. It's like not a necessity. And so my decision to pursue an MBA was a bit, not controversial, but just like not contrary to common practice in the sales profession. And yet it was a really great decision for me, and I got my MBA at Stanford, and it opened up so many doors. That was actually where I first connected with Pear and learned all about their work in supporting

[4:16] entrepreneurs on college campuses. And I actually became a Pear fellow, and that's where I started working with Vanta, which was one of Pear's portfolio companies. So decision to pursue an MBA and a big step towards me being where I am today. And then finally, the last thing I'll say is a pivotal piece of setting me up to do my role today well was deciding to start a company. Leaving Stanford GSB and founding a startup, that was a huge decision. One of the challenges when you go to a program like Stanford, you have so many great opportunities ahead of you and options, and that optionality can sometimes be crippling. And taking the big risk of starting a company was huge, but has really set me up well to both understand founders as an operator, but also as a founder myself. And now at Pear, I've done all the different, if you think about the entrepreneurship landscape, I've been an operator at an early stage company and led teams at Stardust, and also founded my own company, and now working from the VC perspective. I always tell

[5:20] people I'm the best rounded that I've ever been, truly having a great glimpse of how the whole ecosystem works. Significant experience in both founding and leading startups, as well as working in larger enterprises. How did these experiences shape your approach to go-to-market strategies for early stage startups? Yeah, well, I think again, being at Box pre-IPO and then joining ServiceTitan right after their Series A, and then working with Vanta in the earliest days of the company, they've just given me really great perspective. So now in my support of founders, I'm able to give them the context of, this is what a good, big, mature company looks like, and this is sort of what you're working towards in building an organization, go-to-market function. And that perspective, I think, is so valuable to our founders. It helps them feel like I know the whole arc of the journey that they're on, and I'm grateful to be able to provide that to them. And also I've seen across the companies where I've been involved, Box, ServiceTitan, and Vanta,

[6:23] I've learned that the best founders are always selling, right? It's not something that you only have to do at the early stage before you hire for sales people. But really, if you think about Aaron Levie at Box or Ara at ServiceTitan, and of course Christina at Vanta, these are people who not just do founder-led sales really well, but embrace the full journey of being a founder who leads a sales leader as a founder throughout the entire course of their company. See, you specialize in pre-seed investments. What are the key factors you look for in startups? One thing that we're always mindful of is we want our founders to be customer obsessed, and if we can see an inkling of that in founders that come and pitch to us, that always excites us, cuz that's ultimately, again, the backbone of building a successful org is delivering value. And the way you do that is to have a really good pulse of what your customers need, what the end user values, and what you offer. And so that customer obsession is huge, as well as incredible, really deep customer empathy. Again, the

[7:27] best founders that I've worked with and seen have become champions for their customers. They really want to make them successful. That's what they care about. That's what keeps them going and motivates them. And so if we can see that, inklings of that customer obsession and customer empathy, that's huge. And then the other one that I would add is just do-whatever-it-takes attitude for getting in front of customers. We are always wary of founders who are like, oh, well, just tell me how to do cold outbound, or show me some other company's playbook. We really want to see founders who understand that every company sort of writes their own playbook. Yes, taking the best practices from others and learning the fundamentals of sales, but ultimately the willingness to build your own playbook, the willingness to go out and do whatever it takes to get in front of your customer, to resonate with them. And that's something that we love to see in our founders. What are some of the biggest challenges women founders face in the tech industry, and how does Pear VC help them overcome these obstacles? Yeah, tech is tough. It's tough because I think there are expectations to just be

[8:30] working around the clock, and honestly, that's hard for anybody, any parent, not just women, but any person wanting to have a full life outside of work. And mentioned parents, for me, that's always top of mind, cuz I'm a mom of three, and I've seen that especially for women who bear the significant burden, responsibility of caretaking in the earliest days, it can be so challenging. Pear, I'm so proud to work at Pear. We bringing diverse perspectives into the tech industry and empowering women to feel like they are capable of doing what might seem impossible from the outside. So we do that by equipping our founders with a lot of hands-on involvement. That's one of the reasons that we come in and provide support around talent, growing your team, and go-to-market, figuring out the right motion for your team. But we're also really big believers in the power of community. We have studio spaces that we make available to our founders where they can work there and collaborate with one another. And so I think a big piece of, for women, is being able to see other examples of women that are doing

[9:31] it, learn from them, how are you doing it, is so critical. And so we also have a Female Founder Circle program, and that gathers women and again builds that community. We're regularly spotlighting and bringing in speakers, again, can be those examples for our founders. And even personally, I like to say that I'm known actually as someone who often brings my kids into the office for events. So Pear is known to host lots of great happy hour events or events for founders that happen after the workday, and I often choose to bring my kids to those events, cuz I don't want to, I don't like feeling like I'm either with my kids or at work. I really am passionate about blending both of those worlds, both of my worlds, and Pear is a place where that's not just tolerated but celebrated. My teammates often say, your kids are part of the Pear team, and it's little things like that that I feel like make a huge difference, and the way that Pear is chipping away at things that make it really challenging for women and for parents in general. You created Vanta's first sales playbook. Can you share some of the essential components

[10:34] of the successful sales playbook for early stage startups? Yes, so again, just repeating what I'd said a bit ago, I really feel that it's important for founders to have the right perspective and understand that using some other company's playbook is not the best strategy. We want to see founders that come in and understand, yes, there's best practices, things to be learned from other motions and from other companies' journeys, but ultimately creating a sales playbook is a very, should be a very iterative and company specific process. So I think that's the first thing that I'll say. And the backbone of any good sales playbook is a successful run with founder-led sales. And I think that's what, definitely when I had at Vanta in working with Christina, she was already, again, customer obsessed. She was already doing so much of the core important stuff of sales, is listening well, taking the language that her customers were telling her and sharing that back with them with her market messaging that way. And so doing founder-led sales really well is the first piece of really unlocking a

[11:37] good sales playbook. And then from there, you're really codifying all of what you're already practicing, so putting in the playbook. And the way to think about a playbook is, this is an asset that your first sales hires are going to use to learn how to sell, right, and learn how to take what the founder has done and amplify that. And so putting together a history of the company, I love seeing that, and team values in the playbook, just so the reps know this is the heart of what we do, this is why we do what we do. Including a summary of the market need. At this point, when you're writing a playbook, you already have a sense for what resonates with your market and what is most top of mind for them. Any explanation of technical terms or guidance on how to demo, almost like teaching your first sales reps, again, how to follow the same model that the founder has found success with. And then of course an overview of ICP and competitors, or notable customers that they should mention on their calls, and it can be really good. And then any guidance on lead gen, how to source, where to source meetings, how to qualify, lead is a good lead or a bad lead, and what

[12:40] are the stages of your sales process, really documenting that very well, and then describing how you move, how people graduate from one stage to the next. And then of course having objection handling guidance, so language around, what do you say when someone objects with this, or how do you talk about pricing and how do you bring that up. Those are all kind of core parts of any sales playbook, I'd say. But again, the backbone of the playbook is ultimately a successful run founder-led sales, and a founder who has done, gotten in the trenches and has really gotten comfortable with running their sales process themselves. How do you see the role of technology and innovation evolving the context of GTM strategies for startups? Yeah, we're living through such an exciting time, and it's honestly one of the reasons why I'm thrilled to be at Pear in this particular moment in history. With AI, I think AI is just going to transform so much of what go-to-market motions look like. I'm particularly excited about tools that can provide more intelligence and just insights via

[13:43] connected systems. I think right now a lot of the work that happens in go-to-market still can feel siloed, like I have this tool for this and this tool for that, but the ability to bridge those systems and work more effectively is really exciting. I'm a big believer in empowering sales people to be better at what they do, and I think I'm less in the camp of AI is going to completely replace the sales profession. I definitely don't feel that. But AI, I think, is really going to supercharge capabilities on the go-to-market side, and it's really exciting. It's a great time. A leader and mentor, what advice would you give aspiring founders looking to advance their careers in tech? The first one is going to maybe sound cheesy coming from me, but it really is to embrace sales. I think a lot of people feel, a founders feel like sales is a necessary evil, in a way, like, okay, I'll do it for however little time I need to, but then as soon as I can hire someone, I want to hire someone so I don't have to do it. I think really shifting that mindset is so critical, understanding that sales is something that you're always going to be

[14:44] doing, whether it's you're selling your, even if you're not a founder, but you're selling your own work or your own candidacy for a promotion, right? That's, in a way, a sale. When you're hiring someone, selling the opportunity, right, recruiting someone is a form of a sale. Of course, anytime you're raising capital, you're selling the idea, you're selling the opportunity to VCs. And so I think honestly the best advice that I could give any founders or anyone early in their career is to just embrace the sales mindset, to understand that communicating and convincing someone of something, of a viewpoint that you have, is such a critical core skill that is not something that's optional for a career. What are some of the most effective customer strategies you've implemented or seen in early stage startups? Yeah, I think, I mean, the overarching theme I'd say in the most successful customer acquisition strategies is just effective ways to get in front of your customer, right? How, effective ways to build that relationship, effective ways to have an

[15:47] audience with them. And so one that comes to mind is at ServiceTitan, and I think we did this so well, we really prioritized going to conferences, and our early go-to-market was completely fueled and filled by those in-person experiences that we had with our customers. And I just can't overemphasize the importance of that in-person relationship building. So I would say finding a way to get in front of your customers face to face is crucial, especially early on. Another one that I think is counterintuitive for a lot of people is to start really narrow. I think especially for founders who have raised capital, they've gone from selling this really big vision, like we're going to take over the world, and this is how large our market is, and we can be so big, to then pivoting to actually focusing very narrowly on one particular part of the market, one particular use case. And the idea there is that if you can narrow and build a lot of great customer referral and make those people

[16:50] really happy, that that will balloon into allowing you to take more of the ecosystem. But I think a lot of people find it hard to really focus and hone in, but I think that's a critical go-to-market strategy that shouldn't be missed, especially in the early days. And then the other one that I'd say is social selling and building a thought leadership, really getting out there and showing your unique perspective, sharing your unique vantage point. And I think that can be so huge for founders, especially in the early stages of building that trust and helping people see that you really have a unique new insight into whatever problem it is that you're solving. Startups setting the pricing model? Yeah, this question is actually one that comes up all the time. As you can imagine, our founders are really early. Pear invests at the pre-seed and seed stage, so we're writing the earliest checks, and it's often like, okay, now I have a product, how do I even think about pricing it? We, and

[17:53] I have to make a plug here, we actually have an upcoming session on our series Winning Wednesdays where we're going to talk all about this with Mike Molinet, who was a co-founder at Branch and is now running Thea, and co-founded Thea. They've gone through six pricing iterations over the last year, and so he's going to join to talk through what considerations founders need to think through as they land on pricing. The advice that I'd give is it's an iterative exercise. As you can, even with that example I just gave of Mike, he's gone through six iterations in one year. And so I think in the early days, you're really start wrestling with it and feeling it out. But some important guidance that I provide to our founders is you don't want to start undersell yourself, like start too low with your pricing, because it's harder to go high, like raise the price, than it is to lower it. And you can always use discounting strategically to land somewhere feels right for your user. But if you don't set the price high enough early on, you kind of undercut your ability to figure out what the ceiling is for your customers' willingness to pay. So I think one big

[18:55] piece of advice I give our founders is don't go too cheap too fast. Try to figure out what that ceiling is for your customers' willingness to pay. The other big thing that I have been talking to our founders about recently is thinking more creatively around structure for pricing. For decades now, we've all gotten really accustomed to the per user per month pricing, and I think we forget that historically, Salesforce really is the company that made that pricing model popular. Before that, it was just flat fees for on-prem services and solutions. And so if you think about the tech revolution that Salesforce led in that new pricing model, I think we're living through a similar time now where pricing is going to change. Because if you think about AI and how AI is going to make everyone more productive, a per user per month model, if there's less people, it's sort of like it will cannibalize itself over time, right, if you're truly driving more efficiency. And so, and it'll cap your growth in the future. So I've been

[19:57] encouraging our founders to think again creatively around value based pricing or output based pricing, aligning pricing with whatever is driving your customers' willingness to pay. Again, really exciting times to be navigating those questions, because I think we're living through an exciting revolution in how we price software. What are the components of an effective sales process for early stage startups, and how can they optimize these processes as they scale? Important early sales processes, we call it sales hygiene, is making sure that you are tracking data, being mindful of data from very early on, like having a strong sense of, from this many meetings, this is how they converted into a demo or a trial. Really having a good pulse on how you are moving people through the process, the buying process, is really critical. Part of that is also establishing clear stages and defining them, understanding your own objectives and what you're trying to get or provide your customer through each stage. And a big piece of that early on can be super simple, as simple as just recording

[20:59] conversations and taking copious notes. I think a lot of our founders, it's sort of, again, not intuitive to them to do that, but it's really important to be able to document well so that you can then extrapolate and revisit and think through how your sales process is changing, or where you have opportunities to make it more efficient, more impactful for the end user. So really, and being mindful to document and track is really critical. And then I think also a really important part of the process for early stage founders is also being intentional, so driving with not feeling so much like the customer is the one that dictates what the next step is and the next step is, but really trying to figure out, help your customer learn how to best engage with your product and how to best get to a point of decision around a purchase. And so really being intentional and taking, driving more of that conversation, I think, is critical for a sales process in early stage companies. Sorry, just to answer how you scale that. Once you grow beyond founder-led sales and you have, after you've

[22:03] built some early, your early team, the way you expand that early sales hygiene is just you operationalize it, right? And that's where it comes to bringing in software that will support with that. But early on, again, I would say it's the same fundamentals of sales hygiene. It's just a matter of how you track. And early on, it's easy to be scrappy and you don't need a lot of tooling, but then as you grow, tooling can really help. How important are customer introductions in early stages of a startup, and what strategies do you recommend for leveraging these introductions? Yeah, I think I have sort of a hot take on this. We, at Pear, we intentionally want to, we're mindful of teaching our founders how to fish and not just feeding, giving them fish, right, that we've fished. And so we want, of course, customer introductions are critical, right, and leveraging your network is a really important part, especially in the early days. But we want our founders to be really mindful of getting to the truth, or getting to actual users that have the pain. So for example, making an introduction to a company and having a

[23:06] first meeting with them can feel like, they were willing to meet with me, they excited about my product, but it can also almost be a fake signal, right, and they were just doing it to keep the relationship warm, or to do their friend a favor, or something like that. And so you have to be really careful in the early days, suss out where there's real customer interest and pain and curiosity, and where someone's just doing you a favor. And I think that's the danger when you make customer introductions, of like not being able to parse that out. And so in the early days especially, again, a warm meeting can be valuable as a learning opportunity, but getting someone to answer a cold outbound is a real signal, right, that there is something there that resonated with them. And so parsing through what is a favor and what is actual signal, I think, is really important, and founders need to be honest with themselves as they look at and navigate customer intros. But the most important thing, I think, is in taking these customer introductions is to learn and to be willing and open for them to redirect you. I think a lot of times what can be, again, the customer readers can be a

[24:07] little bit misguiding is that go to a call and you want to just pitch them on what you've already built, or like what you're thinking about. I have a really good idea and you want to tell them, share your good idea. But you have to approach those calls with a willingness to be redirected, a willingness for them to say, actually, that's not exciting, and what's actually a big pain and need is this. And so having that aperture and that willingness to, that's how I would approach those calls, is a sense of like, I'm not there to school them. Like, I want them to have an opportunity to school me and to tell me if I'm missing something here, or if I need to rethink this. I think that's especially important for warm introductions in the early days. On a final note, I want to ask you about building strong GTM motions. What are some of the core components here, and how can startups ensure they build these effectively from the ground up? Yeah, again, I think the core component, if you want to have a motion that really works, is iterating, a willingness to test, make a hypothesis and then test it, and really allow the data to guide you. It's really important to be customer obsessed as well, and I can't overemphasize this, but

[25:10] just letting your customer empathy, your customer curiosity, wanting to really truly be a champion for your customer, wanting to help your customer be the hero of the story, that's so important to actually landing a strong go-to-market motion. And the way I would even think about, do I have a strong go-to-market motion, is you want to, do you have both push and pull in that motion? And push is when you're trying to reach out to someone and you're trying to get them on a call. Pull is when they're coming in down, right, and they're saying, hey, this is interesting, this is something that I need. A great go-to-market motion has both of those present, right, where there's both this outbound and you're trying to share and educate folks around your product, and then pull, where there's sort of this natural, like inevitable, like almost desperation, like we need this, we need yesterday. And so you really want to try to land on both that push and pull. But I think the most important components of a strong go-to-market motion are really the backbone of them is both that customer obsession and then the data, and the focus on letting your data guide you

[26:15] in your next steps. And then also one thing that I always tell our founders is starting your go-to-market in a strategic way to where every sale makes the next sale easier, right? And thinking through, is the work I'm doing today setting up a good precedent for tomorrow, and am I building momentum in the things that I'm doing today? I think especially early on, you want to try to position yourself in a way where you're really building that momentum. Does it for this episode of the GTM Vault Podcast, and Anna Levya, thanks so much for joining us. It's been