Pod Insights a16z Podcast Doubling Down on Founder-Led Sales with Pilot's Waseem Daher About this episode In a new episode of My First 16, a16z partner Seema Amble talks with co-founder and CEO of Pilot Waseem Daher on how he thought about the importance of charging, how secondary signals often matter in an area like accounting, and never stepping away from doing founder-led sales.
My First 16, a new video podcast from a16z, features interviews with founders and CEOs of fintech companies about how they acquired their initial customers and the hard lessons they learned along the way.
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Transcript 0:07 Speaker 2 Hi, I'm Seema Amble, Assassin FinTech Investor at Andreas and Horwitz. The number one question I get asked by early B2B FinTech founders is how do I acquire my first set of customers? As well as how do I get my customers to trust me with their money? In my first 16, I chat with the founders of several prominent fintech companies and ask them about how they targeted their initial customers, what they did to win their business, and their hardest learned lessons. Today, my guest is my friend Wasim De Hare, a three-time founder and currently the co-founder and CEO of Pilot, which provides bookkeeping, CFO, and tax services for startups and growing businesses. Given his experience, Wasim has a wealth of knowledge about finding customers in different contexts.
0:53 Speaker 2 We'll hear from him on how he thought about pricing and the importance of charging. Hint, no one wants a discount surgeon. Also, how secondary signals often matter in an area like accounting where customers can't try before you buy, and never stepping away from doing founder-led sales. Let's jump in.
1:16 Speaker 1 Wasim, thanks so much for uh for hopping on.
1:20 Speaker 0 Thanks for having me. Great to be here.
1:21 Speaker 1 Why don't you start by laying the context of sort of the founding story of Pilot and how you guys got started?
1:28 Speaker 0 Sure. So the founding story of Pilot is interesting. It's very, very intertwined with I guess our whole journey because my co-founders of Pilot were all folks that I met at MIT in undergrad. We'd also have computer science together, and this is actually the third venture for the three of us. And one consistent theme across all three of the ventures we've been up to is they've been about solving deep personal problems. So the first startup was technology that could apply software updates without rebooting for Linux. This was a problem that my co-founder Jeff had in administering Linux systems while at MIT. Our second startup was a group chat tool, which was born out of pain. We had communicating with our team in our first startup. And then Pilot, as you noted, we do accounting, we do tax prep, we do a CFO services for high growth startups.
2:14 Speaker 0 The reason we started it is because this was such a pain for us in our previous ventures, and we had deep conviction that the problem could be solved, could be solved better, that the future did not look like what happens today, and we felt we were the ones who could build it.
2:30 Speaker 1 Awesome. Um you want to just walk us through what you thought about as like the MVP product and what you wanted to start off with going to market with.
2:40 Speaker 0 Sure. So we had a very kind of firm opinion up front, which is I think the the quote unquote normal thing a tech company would have done here is to say, look, the state of accounting is slow and unreliable and tedious and incredibly manual. We are gonna build a better software tool that will sell to entrepreneurs or will sell to accountants. And our perspective was no, we're not gonna do that because I have never ever in my entire life heard a founder or a business owner say, I can't wait to buy accounting software. Like, no, what the founder says is I really need someone to solve this problem for me. I need someone who feels like they're on my team, someone that has my back that can take care of this for me. So as a result, we're a kind of weird shaped company, right? We're a tech enabled service. From our customers' perspective, we're an accounting firm essentially.
3:28 Speaker 0 But of course, when I close my eyes and thinking about the company, I think of it as a tech company. So as we thought about what was the minimum viable product, the minimum viable product on day one was well, you need to be able to do the bookkeeping for your customers. And the good news about that though is they want it done, they don't really care how it gets done. And what you can do on day one is the same thing any accounting firm anywhere else in the world does, which is you can do the accounting by hand in QuickBooks, which is exactly what we did.
3:59 Speaker 1 Right. And I I feel like a lot of companies in your shoes, um, the the service or the the software being provided, or sort of the product being provided seems seamless and fully tech enabled to the customer. However, in the back end, you know, as people like to say, there's a lot of bubblegum and duct tape. Um so I'm curious, just if you wanted to just put a finer point on exactly what you what you were offering to their initial set of customers and then what was going on in the background, I think that'd be helpful to share.
4:27 Speaker 0 Absolutely. So we started the company basically in January 2017. And the first thing we did is we called up startup founders in our network, and the conversation went something like this. It was, hey, what are you doing for your accounting or bookkeeping in today? Oh, nothing. Well, what if we do it for you? And the answer was like, okay. And so what happened is Jeff and I are literally in QuickBooks doing the books for these companies, and then Jessica is looking over our shoulders and observing, like, wow, this piece is particularly slow. This piece is particularly air prone. Let me write the first few lines of software that will help do the most obvious, most tedious work more accurately, more reliably. And that's just like such an iterative process. So when we do it again the following month, well, we run Jessica's Python script, some stuff happens, the humans do the rest, so on and so forth.
5:17 Speaker 0 And over time, you know, the computer is doing more and more and more. And the account manager, in this case, me, is doing hopefully more of the high value, more of the white glove, more of the hands-on experience.
5:29 Speaker 1 So you you started with your MVP there. Um, and how many of how many folks were working on it? You had your three co the three of you co-founders, who else was was involved in the early days.
5:39 Speaker 0 Yeah, so we were fortunate in that basically right out of the gate, we were able to raise a pretty large seed round because it was our third venture, because we had two exits prior, et cetera, et cetera. Um, so the first two hires we made were two early engineers. So it was the three co-founders and then our two initial employees, both of whom were on the engineering side.
5:57 Speaker 1 Yeah, and that's not uncommon. I mean, I think we often hear, you know, you you've got to get the product out, and well, we'll transition to talking a little about your first customers, but gotta get the product first, focus on the founders and the early employees talking to customers uh versus you know, bringing in the go-to-market people too early when you haven't actually gotten the product that's ready to put in front of um in front of customers.
6:18 Speaker 0 Totally.
6:19 Speaker 1 Um would love to walk through a little bit around your first customer set, who you targeted, et cetera. So, you know, tell me about who you first wanted to put uh pilot in the hands of and and how you maybe defined your ICP if that's what you called it, and did you did you work with them as design partners and just a little bit about how you thought about your first customer set?
6:37 Speaker 0 Yeah, so the interesting thing about the shape of the problem we're tackling accounting, or maybe I should say the back office generally, but if we limit ourselves to accounting, well, literally every business in the world has the problem. Ranging from the tiny, you know, mom and pop operation to the precede founder to the thousand-person company to literally the Fortune 500. And so, in a sense, like the TAM or the like possible customer was everyone. And so obviously we needed to kind of scope that down considerably to have some hope of building something that had good appeal to initial customer base we could serve well. And our initial target was technology startups and in particular early stage technology startups. And the reason for that is sort of threefold. One is we knew they had the problem. We knew viscerally that they had the problem because they were us and we had the problem.
7:26 Speaker 0 So there's a lot of shortcutting you could do just to understand what it is you should build. The second is they have actually a quite hard version of the problem. And what I mean by that is the needs of the company when there are two people and it's you know pretty revenue and they're in the garage and the needs of the 300-person startup with the VP of finance and the controller and the full-time finance team are very different. And then the third and obviously like quite beneficial aspect of selecting technology startups is they were in network for us. We had good credibility there. It was just an easier on-ramp to be able to attract and retain those initial customers.
8:03 Speaker 1 Yep. And there's obviously a very wide range of startup customers, and you guys have great networks. Um, how did you pick and choose among uh the potential startup customers you could be working with? Were there a particular stage in terms of like series of funding, uh, complexity of books, or you know, how did you how did you narrow that down further?
8:24 Speaker 0 We were pretty open-minded in the sense that I think we were in the process of discovering kind of where it best fit. And we found that there were sort of two paths. There was net new, like, okay, the company is just existed, they haven't hired someone, they need a solution, like we should plug in there. But the other, and it was a little bit maybe surprising that this was uh this was an option, is folks who are basically unhappy with their current providers. And the rate of sort of latent dissatisfaction here is actually pretty high. So we have a number of switchers as well, and I think that was an interesting insight in the early days because it actually has a lot to say about the motion with which you acquire the companies. Meaning, if you have to be the first one in because you're never gonna get ripped out and replaced, that's very different than well, every year potentially you can take a crack at you know, winning the engagement, depending on whether the customer is happy with what they're doing or not doing.
9:19 Speaker 0 Like you're probably not gonna rip out your payroll system or your corp card or your bank account. It's just or your like, you know, your credit card processing system is just so onerous once those are in to remove them. But what we found is actually folks were very willing to switch from their existing accounting solution over to us in a way that frankly was a little bit surprising in the early days.
9:41 Speaker 1 Got it. So you had these two camps, it sounds like the the the net new and then the disgruntled. Um how did you think about going, you know, yeah, resin, you know, getting that message out in the market saying, Are you you know, it was it saying like, are you disgruntled, don't want to, you know, don't want to spend so much time thinking about uh bookkeeping. Um in accounting, or you know, how did you think about that early messaging in the market?
10:04 Speaker 0 In the early days, what we really positioned ourselves as like, well, we are the tech enabled, we're the modern, we're the like forward thinking like four startups by startups option, we really get what you're about because we ourselves are a startup, and like look at our founder startup track records. Like that was really sort of the narrative that we advanced in our customer base, which was accurate, by the way. And I think that's what made it possible for them to trust us as a new company, which is like, okay, look, this is a seasoned team, they know what they're doing, they've had this problem themselves. Like, sure, I'll give it a shot.
10:40 Speaker 1 And is there somewhere where you shared that story, or was it more word of mouth? Um, you know, what when when you say sharing the message, what did what did that mean? Because you know, a lot of times companies are using case studies, et cetera.
10:51 Speaker 0 But
10:51 Speaker 1 again, you guys have a great network, so I'm curious how much of it was just word of mouth.
10:54 Speaker 0 Extremely word of mouth driven, and then we leaned very hard on our investors as well, because that's sort of a natural distribution channel for us, which is like, okay, you have other companies in your portfolio. A hundred percent of those companies have this problem. Like, can you make some interest for us? Um, and then there's also some natural like timing stuff, like, okay, the end of the year happens, like you have to think about taxes, there's some natural like times maybe that people are more in market than others, and then we just ask our customers very regularly, look, if you're happy with what we're doing, are there other people you think we should talk to?
11:29 Speaker 1 Got it. And so did you have a formal referral program, or was it just uh just like courtesy of like, okay, we like this and and and please refer us to other folks in your in your your network.
11:41 Speaker 0 For a long time, it was literally I just would personally email you and I'd say, hey CEMA, I hope you've been having having a good experience with pilot. If you have any feedback from me, please let me know. Listen, if you're happy, we'd love an intro to anyone else in your network who's thinking about this. Got
11:55 Speaker 1 it.
11:56 Speaker 0 And then of course, eventually we introduced like our furrow program that actually monetizes that in some way. But for longer than you would think, it we were really kind of resting on the caliber, just like that the experience was good. And in particular, the experience just felt a lot better than maybe what you were used to, you know, what you were used to getting from another provider.
12:16 Speaker 1 Got it. Um, and then on the investor side, anything that you did to uh nudge the investors, obviously, like you know, sitting in the investor side, we wish we always wish we had the numbers faster and sooner, right? So um there's an aligned incentive, I would think, and that often drives the the refer to to to act faster. Um but I'm curious if there was anything you had to do on the investor side to nudge them to act.
12:39 Speaker 0 Yeah, we had a bunch of investors in our seed round, like a bunch of like quite prominent angels, folks that honestly I would have paid money to get advice from, so it was nice to get both money and advice. Uh and we used to do a thing in our monthly updates back then we did in monthly investor updates where we basically had a referral leaderboard. We're like, thanks to these people for sending you know XYZ referrals this month. So we like tried to gamify it a little bit, uh, which I think for some of our investors definitely did light the fire under them a little bit.
13:07 Speaker 1 Um, you know, a common question that comes up is did you charge and uh the early customers um and especially in the context of a financial transaction when you want to win that trust, you're often willing to make more of a sacrifice, right? On the payment side. Um so I'm curious how you guys thought about pricing early on and how much time you spent on it, and now reflecting on it, what you what you think about that.
13:31 Speaker 0 Yeah, we absolutely charge on day one. I think it's super important too, because it is the clearest signal that you are actually solving a real problem that folks have. And now, admittedly, like we've 10x to the ASP, you know, since then. And there's a lot, of course, that we do now that we didn't previously do, but very clearly we did not pick the correct price point necessarily, or perhaps we didn't have the brand that allowed us to command the price point we can command now, or you know, we couldn't deliver the work at the quality that we can deliver it now. I think it is important to charge. Um I think in the early, earliest days, the pitch was something like, look, people plus software working together, tech enabled, it's gonna be faster and cheaper and better. And like I think a big part of the narrative was technology allows us to make this cheaper.
14:20 Speaker 0 And we've pivoted pretty hard away from that because it it's actually not what the customer wants, particularly in this kind of high trust scenario. Like folks are willing to pay more if it's better. Like they care a lot more about it being better than they do about it being cheaper. And if you're better and comparably priced, that's actually I would rather pick that option than the cheaper and less good option. Or maybe the like cute way I like to say this is you know, people are not looking for the discount surgeon. They like this is an area where you're willing to spend a little bit to make sure it's right.
14:55 Speaker 1 Yep. And does that mean, you know, you guys ended up there were people who were not good fits as early customers, or even now, and you know, it's a common thing for um, you know, some of the best founders to be really judicious about who they target as their first customers, uh, and even you know, as time goes on, fire customers. So I'm curious um if uh that meant that there were customers that you were like, thanks, you know, we we love that you're interested, but no thanks, it's not gonna be a good fit.
15:20 Speaker 0 Yeah, one class of customer that we still turn away today, and a lot of the sales process at the moment is really about making sure that we're gonna be able to do a good job for you. Like you come to us, you're like, we we need accounting, we know we need accounting, you seem good, like let's do it. You're actually willing to buy in some cases where we're not a very good fit for you. And it's actually interesting and difficult to kind of train the team to say, well, no, even though you want to and you you're you know, you're willing, you shouldn't, because we won't serve you well. And in particular, the places, one example today, it's like there's a whole class of kind of very small business, like solopreneur type operations, where realistically they do not have the budget for any external accounting firm. And now my hope is at some point, you know, we will have advanced enough on the technology side, we will we will have been able to drive down the prices sufficiently that we can feel the high quality offering for those customers.
16:16 Speaker 0 But today it's a if that's kind of the bucket you're in, the reality is we're just not a very good fit for you, and we tell you that.
16:23 Speaker 1 And yeah, if you don't mind me asking, how how do you tell folks that aren't a good fit? Like, thanks but no thanks.
16:31 Speaker 0 Well, I mean, part of you're able to do some of that via pricing, which is your price point, is just there's no intersection between your minimum price and the maximum price they want to pay. And the second is we're very we're very blunt with customers. We say, listen, we've found that we work best for companies, you know, that spend at least 30k a month or whatever it is, or that have revenue of a certain amount. And if your revenue is under that amount, you're probably just like you probably should not select us. Like our rule of thumb is basically you ought to be spending something like one percent of your total expenses on the accounting. And that kind of like passes the smell test too. Like to exaggerate it. If I were like, you should spend 10% of your expenses tracking that other 90%, like that feels wrong.
17:19 Speaker 0 Like it should not be the case that you're spending a material amount of your money tracking the rest of the money. So we've found that like one 1.5%, like that's good and healthy. If instead that number is 10% or 20% or whatever, it's like, well, there's just not a good decision for you, the business owner.
17:37 Speaker 1 Okay, well, so we've talked a bunch about like the you know, first customers who you targeted pricing. We'd love to talk a little bit about you know, team, you know, given that the team was really technical starting. Like, how did you think about founder-led sales and how long you wanted to do that when you brought your first um go-to-market hire in?
17:57 Speaker 0 I'm like the world's biggest proponent of founder-led sales. I think it's like the best thing ever. I still do a bunch of sales stuff myself personally now in year, whatever, six or seven of the company. Um, so I think people try to leave the founder-led sales regime too early. And I think it's a big mistake. For us, I was the pilot sales team for the first year, and then about a year. And then basically, like around September 2017, so you know, nine, 10 months of the company, we had about 60 customers. We were probably already doing about 250k of ARR. We made our first hire on the sales side, and I was still like quite quite hands-on, quite directly involved. And then our second hire wasn't until almost a year after that.
18:46 Speaker 0 It was until August 2018, we had 240 customers. We said, okay, fine, we now have built enough of a scalable, repeatable process that it makes sense to try to build a professional team around this.
18:59 Speaker 1 Got it. Yeah. Well, well past the first 15. You uh Certainly. You had uh you until you waited until hiring a government person.
19:07 Speaker 0 And the reason for that is just like when it there are so many reasons. One is obviously it informs like how you think about the product roadmap, there's all sorts of feedback you get from talking to customers, helps you think about the messaging, because you're the sales team, you're the marketing team, you're the customer success team. Like you need all of these inputs from the customer. And then also if it doesn't work and you've hired someone else to be the sales rep, when it doesn't work, you don't actually know whether it's because something is like off with the product or whatever, or maybe you hired the wrong sales rep, or maybe you gave the sales rep the wrong like message. Like when you disintermediate yourself from that feedback, it just makes it harder to debug when things don't work.
19:52 Speaker 0 And then also makes it harder to improve because you're not learning as rapidly. So I think folks, like founders should absolutely like insert. themselves into that stream of knowledge because that's how you make the company stronger.
20:05 Speaker 1 Yeah. No, and it's funny, I mean, I was talking to someone who's at a pre-IPO stage as a CEO, and it's he takes customer calls every week. Um, and I'm sure it sounds like you are as well, but getting that voice of the customer directly um just influences so much right across product, your processes, etc. And like really getting that tangible feedback is um is is it can't it just can't be replaced.
20:29 Speaker 0 Totally.
20:30 Speaker 1 Um got it. And the and when you hire that first go-to-market person, any particular profile you looked for to kind of compliment your background, um, or you know, were you open to different different backgrounds?
20:42 Speaker 0 Yeah, so this was interesting because I had also done a bunch of the sales and marketing at our previous startups. So I felt like I like knew how to do it, or I knew how to do it as well as a technical founder could. And so what I was really looking for was just a smart talented generalist who wanted to get into sales. Because I there was still a lot we were still learning about who we were selling to and how we were selling to them and kind of what they needed and exactly who we're gonna target. Like it it didn't feel like the time to bring in, oh, this is a talented AE who is sold, you know, who like consistently exceeded their quota quarter over a quarter at Salesforce or whatever. Um I think we were still kind of feeling like scrappier earlier.
21:28 Speaker 0 And so that first hire was um the smart talented generalist, this woman named Kate, who was awesome. And she and I just worked super super closely together. Like on all the deals from that point on. And it wasn't until a year later until that August 2018, um, when we hired our next rap guy named Ryan, who's actually still at Pilot, which is awesome. Um, and he came from a more traditional AE background. He had had an AE role, he had had AE roles previously, like but I think we were ready for that at that time.
22:00 Speaker 1 Yeah, no, and it's it's actually a not uncommon. Yeah, I have a company right now where the founder is still doing sales and has brought in uh a generalist who's just really high uh you know, high output, high urgency, high energy, um, who compliments the founder in the sales process. And even though they don't have a formal sales background, uh, they're able to do, you know, help build out the pipeline, just think through the feedback and really process a lot of it in a way that you know, maybe a traditional salesperson who's more focused on the craft of just sales isn't able to do. Yeah, I guess last area we've we've talked about your initial customers, scaling up, team, etc. Um, would love to just touch on advice or things you've done differently, and and you've got the the privileged position of having gone through this journey multiple times.
22:47 Speaker 1 Um, would love to hear, you know, any advice you have just in terms of what you might have done differently, um, or what you know founders should be spending time on early in the early days um that uh maybe wasn't obvious when you you first went through it.
23:01 Speaker 0 Yeah, I think uh it's not that this is obvious not obvious, I think it is pretty obvious, but it's uncomfortable, which is look, you gotta go get customers. And the reason is because that's the only thing that that really validates whether you're making something people want. Because ultimately you're in the business of am I making something that people want that they are willing to pay for? And the only way to determine that is to try and see by talking to people whether in fact you have done something that they want that they are willing to pay for. And so the piece of advice is look, you have to just put yourself out there and it's awkward and it's uncomfortable, and people say no, and it hurts your feelings and like, but it's necessary.
23:44 Speaker 1 Yeah, and it sounds like, but it sounds like the the still the process of doing that cold outreach, you know, whether it's the computer club or you know, uh account accountant Facebook groups, which we often see, or dental Facebook groups in the way that people sell sell to dentists, surprisingly. Um, you know, it's that it is getting that wherever you have the in, sort of nav going from there and kind of seeing where you can where you can navigate.
24:06 Speaker 0 Totally. And the thing to remember is like in general, not always, but in general, people want to help you. Like you're a startup, like people like startups and saying and like not trying to hide it, like, hey, you know, I'm a startup founder, we're doing this new thing, like I would really appreciate it if you could just spend 15 minutes talking to me about whether we have like people want to help you out, is what I sort of found generally.
24:29 Speaker 1 Yeah. And it's interesting. A lot of our companies often find that those initial customer discovery calls, you come back and they actually those people, because they're open to having these conversations, are also the people who want to try new software or like help you because they're and they're curious, right? And so um, you know, that that conversation doesn't just end at that point, it's often a longer relationship, or at least you can find a few um a few great leads from that first set. Um, and so it, you know, it's a gift that keeps on giving over time.
24:58 Speaker 0 100%. I think like we approached these early conversations genuinely not trying to sell anyone anything, but we found that some subset of those folks were in fact great initial customers.
25:10 Speaker 1 Awesome. Anything you would just say looking back, like don't spend time on this in your initial customer development. Uh it's it's not a good use of time.
25:20 Speaker 0 I I think people can get very hung up on like having the thing be perfect, whatever the thing is. Like the product does not need to be perfect, the deck does not need to be perfect, the collateral does not need to be perfect. Like you just have to get things to good enough because the way that they're gonna get to perfect is by like interacting with the real world, not by your continuing to polish it like in your office. And so I think that's probably just like uh I think you gotta put yourself out there earlier than you otherwise would. And there's a temptation, there's an embarrassment that causes you not to do that, and I think it's ultimately harmful.
25:53 Speaker 1 Yeah. And and was there a way that you guys kept yourselves honest to make sure that you you shipped and you got it out fast enough, or was it uh is it is it hard to do?
26:04 Speaker 0 It's hard to do, and I think in the first in the first company, we like spent a year writing code before we like talk to anyone, if I recall. I mean, this was like you know, 15 years ago at this point. Um so it is a very it's very easy to kind of like fall into that trap. Well, oh, we really need this feature before we can whatever. And maybe, like, maybe you do need the feature before it's a usable product that you can actually sell. But the first thing you're gonna do is not like get the sale. The first thing you're gonna do is like that market discovery, and you can do that with nothing but like a little sketch on a napkin or whatever.
26:37 Speaker 1 Yeah, no, and I I feel like a lot of times founders forget that they this especially if you're more of a technical founder, you can you can pre-sell or whatever that means, you know, that can mean a lot of different things, but you can have those conversations, you can get a pretty good shape of what the product might be before actually having a product to put in front of people. Um, and and as scary as it is to sometimes have that conversation or even sort of fudge where you are in that journey, um, it it uh it can also save you a lot of time in terms of developing the insights.
27:06 Speaker 0 Absolutely.
27:07 Speaker 1 Awesome. Well, yeah, thanks so much for joining me. And and this is uh fascinating to hear the story.
27:12 Speaker 0 Thanks for having me.
27:14 Speaker 2 I'd like to close by thanking my guests for sharing their insights on finding early customers and building strong businesses. You can hear the rest of my first 16 by going to A16Z.com backslash podcasts, and be sure to go to A16z.com backslash fintech for the latest industry-related content. There you can also subscribe to our monthly FinTech newsletter. Thanks for tuning in.
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