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Nov 21, 2023 · 28m · a16z

Doubling Down on Founder-Led Sales with Pilot's Waseem Daher

Waseem Daher · 16m spoken Seema Amble · 8m spoken
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In this episode of Andreessen Horowitz's "My First 16" podcast, Pilot co-founder and CEO Waseem Daher discusses early customer acquisition, pricing strategies, and the vital role of founder-led sales. He shares how Pilot built a tech-enabled financial services platform by focusing on early-stage technology startups and prioritizing trust over low pricing.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →

The host as informed peer 3.0 Guest teaching 4.0 Guest disagreement 0.8 The host pushing back 0.0
05100:0010:0020:001:19–6:19 · The host as informed peer 3/10 Pilot's Founding Story and MVP Strategy Seema prompts Waseem on Pilot's origin and MVP strategy, offering context on how tech-enabled services often mask back-end manual work. Waseem explains why selling software alone fails for accounting, as founders want a solved problem rather than another tool.6:19–13:10 · The host as informed peer 3/10 Identifying and Acquiring the First Customers Seema asks targeted questions about target ICP, investor incentives, and referral mechanics. Waseem details the surprising discovery that disgruntled customers were willing to switch accounting providers much more easily than core banking infrastructure.13:10–17:44 · The host as informed peer 2/10 Early Pricing Strategy and High-Trust Positioning Seema asks about pricing strategy and customer qualification in high-trust financial services. Waseem educates on why cheap pricing hurts trust, using his 'discount surgeon' analogy and outlining Pilot's 1 percent of expenses benchmark.17:44–25:13 · The host as informed peer 4/10 Founder-Led Sales and Scaling the GTM Team Seema relates Waseem's founder-led sales approach to pre-IPO CEO habits and generalist go-to-market hiring strategies. Waseem explains why delegating sales too early prevents founders from properly debugging product and messaging issues.25:13–28:46 · The host as informed peer 3/10 Founder Advice, Iteration, and Episode Conclusion Seema reinforces Waseem's points on pre-selling and market discovery. Waseem reflects on his early founder mistakes of building in isolation for a year before showing the product to customers.1:19–6:19 · Guest teaching 4/10 Pilot's Founding Story and MVP Strategy Seema prompts Waseem on Pilot's origin and MVP strategy, offering context on how tech-enabled services often mask back-end manual work. Waseem explains why selling software alone fails for accounting, as founders want a solved problem rather than another tool.6:19–13:10 · Guest teaching 4/10 Identifying and Acquiring the First Customers Seema asks targeted questions about target ICP, investor incentives, and referral mechanics. Waseem details the surprising discovery that disgruntled customers were willing to switch accounting providers much more easily than core banking infrastructure.13:10–17:44 · Guest teaching 5/10 Early Pricing Strategy and High-Trust Positioning Seema asks about pricing strategy and customer qualification in high-trust financial services. Waseem educates on why cheap pricing hurts trust, using his 'discount surgeon' analogy and outlining Pilot's 1 percent of expenses benchmark.17:44–25:13 · Guest teaching 4/10 Founder-Led Sales and Scaling the GTM Team Seema relates Waseem's founder-led sales approach to pre-IPO CEO habits and generalist go-to-market hiring strategies. Waseem explains why delegating sales too early prevents founders from properly debugging product and messaging issues.25:13–28:46 · Guest teaching 3/10 Founder Advice, Iteration, and Episode Conclusion Seema reinforces Waseem's points on pre-selling and market discovery. Waseem reflects on his early founder mistakes of building in isolation for a year before showing the product to customers.1:19–6:19 · Guest disagreement 1/10 Pilot's Founding Story and MVP Strategy Seema prompts Waseem on Pilot's origin and MVP strategy, offering context on how tech-enabled services often mask back-end manual work. Waseem explains why selling software alone fails for accounting, as founders want a solved problem rather than another tool.6:19–13:10 · Guest disagreement 1/10 Identifying and Acquiring the First Customers Seema asks targeted questions about target ICP, investor incentives, and referral mechanics. Waseem details the surprising discovery that disgruntled customers were willing to switch accounting providers much more easily than core banking infrastructure.13:10–17:44 · Guest disagreement 1/10 Early Pricing Strategy and High-Trust Positioning Seema asks about pricing strategy and customer qualification in high-trust financial services. Waseem educates on why cheap pricing hurts trust, using his 'discount surgeon' analogy and outlining Pilot's 1 percent of expenses benchmark.17:44–25:13 · Guest disagreement 1/10 Founder-Led Sales and Scaling the GTM Team Seema relates Waseem's founder-led sales approach to pre-IPO CEO habits and generalist go-to-market hiring strategies. Waseem explains why delegating sales too early prevents founders from properly debugging product and messaging issues.25:13–28:46 · Guest disagreement 0/10 Founder Advice, Iteration, and Episode Conclusion Seema reinforces Waseem's points on pre-selling and market discovery. Waseem reflects on his early founder mistakes of building in isolation for a year before showing the product to customers.1:19–6:19 · The host pushing back 0/10 Pilot's Founding Story and MVP Strategy Seema prompts Waseem on Pilot's origin and MVP strategy, offering context on how tech-enabled services often mask back-end manual work. Waseem explains why selling software alone fails for accounting, as founders want a solved problem rather than another tool.6:19–13:10 · The host pushing back 0/10 Identifying and Acquiring the First Customers Seema asks targeted questions about target ICP, investor incentives, and referral mechanics. Waseem details the surprising discovery that disgruntled customers were willing to switch accounting providers much more easily than core banking infrastructure.13:10–17:44 · The host pushing back 0/10 Early Pricing Strategy and High-Trust Positioning Seema asks about pricing strategy and customer qualification in high-trust financial services. Waseem educates on why cheap pricing hurts trust, using his 'discount surgeon' analogy and outlining Pilot's 1 percent of expenses benchmark.17:44–25:13 · The host pushing back 0/10 Founder-Led Sales and Scaling the GTM Team Seema relates Waseem's founder-led sales approach to pre-IPO CEO habits and generalist go-to-market hiring strategies. Waseem explains why delegating sales too early prevents founders from properly debugging product and messaging issues.25:13–28:46 · The host pushing back 0/10 Founder Advice, Iteration, and Episode Conclusion Seema reinforces Waseem's points on pre-selling and market discovery. Waseem reflects on his early founder mistakes of building in isolation for a year before showing the product to customers.

speaking balance: gold is the host, purple is the guest (3 minute bins)

0:00 · the host 0% · guest 100%0:00 · the host 0% · guest 100%3:00 · the host 0% · guest 100%3:00 · the host 0% · guest 100%6:00 · the host 0% · guest 100%6:00 · the host 0% · guest 100%9:00 · the host 0% · guest 100%9:00 · the host 0% · guest 100%12:00 · the host 0% · guest 100%12:00 · the host 0% · guest 100%15:00 · the host 0% · guest 100%15:00 · the host 0% · guest 100%18:00 · the host 0% · guest 100%18:00 · the host 0% · guest 100%21:00 · the host 0% · guest 100%21:00 · the host 0% · guest 100%24:00 · the host 0% · guest 100%24:00 · the host 0% · guest 100%27:00 · the host 0% · guest 100%27:00 · the host 0% · guest 100%
Sharpest disagreement ▶ 13:31 Rejecting Cheaper Pricing Positioning

Waseem counters the common assumption that tech-enabled services should lead with lower prices, clarifying that customers care far more about quality in high-trust categories.

 Hardest push from the host ▶ 3:59 Probing Behind the Tech Facade

Seema presses Waseem to clarify what manual 'duct tape and bubble gum' processes were actually running on the back end of their initial product.

 Biggest teaching moment ▶ 14:30 The Discount Surgeon Principle

Waseem reframes pricing psychology for high-trust services, explaining that founders do not want a 'discount surgeon' when it comes to their core financial reporting.

 The host holds their own ▶ 22:00 Validating the Sales Generalist Model

Seema demonstrates her investment experience by comparing Waseem's hiring choices to high-performing generalist sales reps across her active portfolio.
the scores for every segment, with the reasoning behind each
ChapterTopicThe host as informed peerGuest teachingGuest disagreementThe host pushing backWhy
Pilot's Founding Story and MVP Strategy 3410 Seema prompts Waseem on Pilot's origin and MVP strategy, offering context on how tech-enabled services often mask back-end manual work. Waseem explains why selling software alone fails for accounting, as founders want a solved problem rather than another tool.
Identifying and Acquiring the First Customers 3410 Seema asks targeted questions about target ICP, investor incentives, and referral mechanics. Waseem details the surprising discovery that disgruntled customers were willing to switch accounting providers much more easily than core banking infrastructure.
Early Pricing Strategy and High-Trust Positioning 2510 Seema asks about pricing strategy and customer qualification in high-trust financial services. Waseem educates on why cheap pricing hurts trust, using his 'discount surgeon' analogy and outlining Pilot's 1 percent of expenses benchmark.
Founder-Led Sales and Scaling the GTM Team 4410 Seema relates Waseem's founder-led sales approach to pre-IPO CEO habits and generalist go-to-market hiring strategies. Waseem explains why delegating sales too early prevents founders from properly debugging product and messaging issues.
Founder Advice, Iteration, and Episode Conclusion 3300 Seema reinforces Waseem's points on pre-selling and market discovery. Waseem reflects on his early founder mistakes of building in isolation for a year before showing the product to customers.

Statements from this episode (11)

Insight
Daher: Founders want accounting problems solved, not just accounting software
“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, some…”
Waseem Daher Nov 21, 2023 ▶ 3:03
Insight
Daher: Core financial systems are too onerous for companies to easily replace
“Like you're probably not going to rip out. Your payroll system or your corp card or your bank account. It's just, or you're like, you know, your credit card processing system. It's just so onerous once those are in to remove them.”
Waseem Daher Nov 21, 2023 ▶ 9:20
Disclosure
Daher: Pilot gamified seed investor referrals using monthly update leaderboards
“We used to do a thing in our monthly updates, back then we did 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…”
Waseem Daher Nov 21, 2023 ▶ 12:51
Assertion Not checkable as stated
Daher: Pilot increased its average selling price 10x since launch
“And now admittedly, like we've 10 X 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”
Waseem Daher Nov 21, 2023 ▶ 13:43
Insight
Daher: In high-trust services, customers value quality over lower prices
“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.”
Waseem Daher Nov 21, 2023 ▶ 14:30
Insight
Daher: Companies should spend 1% of total expenses on accounting
“Like our rule of thumb is basically you ought to be spending something like. One percent of your total expenses on the accounting.”
Waseem Daher Nov 21, 2023 ▶ 17:00
Opinion
Daher: Moving away from founder-led sales too early is a mistake
“I think people try to leave the founder-led sales regime too early, and I think it's a big mistake.”
Waseem Daher Nov 21, 2023 ▶ 18:10
Assertion Not checkable as stated
Daher: Pilot reached $250k ARR and 60 customers before hiring sales
“Around September, 2017. So, you know, nine, 10 months of the company, we had about 60 customers. We were probably already doing about 250 K of ARR. We made our first hire on the sales side”
Waseem Daher Nov 21, 2023 ▶ 18:24
Assertion Not checkable as stated
Daher: Pilot reached 240 customers before hiring its second sales rep
“And then our second hire wasn't until almost a year after that. It was until August, 2018. We had 240 customers.”
Waseem Daher Nov 21, 2023 ▶ 18:44
Insight
Daher: Pitch decks and products reach perfection through customer interaction, not internal polishing
“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…”
Waseem Daher Nov 21, 2023 ▶ 25:20
Insight
Daher: First customer interactions should focus on market discovery, not closing sales
“The first thing you're going to do is not like get the sale. The first thing you're going to do is like that market discovery and you can do that With nothing but like a little sketch on a napkin or whatever.”
Waseem Daher Nov 21, 2023 ▶ 26:27
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