Pilot has transformed how startups and SMBs handle their financial back office operations, combining technology with human expertise to deliver end-to-end accounting and tax services. As a tech-enabled services company serving thousands of businesses, Pilot represents a new category of back office automation that goes beyond traditional software solutions. In this episode of Category Visionaries, I sat down with Waseem Daher, Founder and Executive Chair of Pilot, to explore how the company built a trusted brand in a high-trust industry and scaled through strategic GTM decisions. Topics Discussed: Pilot's $400K domain purchase decision and its impact on brand credibility The evolution from startup-focused to full SMB market expansion Building a tech-enabled services model in an era obsessed with pure software Creating highly targeted, industry-specific marketing campaigns Scaling customer acquisition beyond founder networks through quality and word-of-mouth The strategic decision to stay in the weeds with customer interactions GTM Lessons For B2B Founders: Plan for success with brand investments: Pilot spent $400K of their seed funding on the pilot.com domain, representing about a third of their raised capital. Daher explained their rationale: "You kind of need to plan for success, meaning in the case that the company is doing super well in a decade, you'll be super happy to be owning your brand." For high-trust service businesses, credibility signals like premium domains become essential sales assets. B2B founders should consider that brand investments may not show immediate ROI but compound over time, especially in industries where trust is paramount. Focus on secondary trust signals for complex purchases: When customers can't easily evaluate service quality, they rely heavily on secondary signals. Daher drew parallels to choosing a doctor: "It's like well, is the office clean? Is it convenient to me, like do they wear a white coat? Do my friends say they're good?" For B2B services that require deep trust, founders should invest in every touchpoint that signals credibility and professionalism, from domain names to office presentation to customer testimonials. Use the hardest customer segment to build generalized solutions: Pilot deliberately targeted startups first, not because they were the best fit, but because they represented the most challenging version of the problem. Daher noted: "The startup ranges from literally we support people that are like the day after they have incorporated...and we support companies with many hundreds of people with a VP of finance and a controller." By solving for the extremes, they built a platform that could serve any customer in their target market. B2B founders should consider starting with the most demanding segment to stress-test their solution's flexibility. Create marketing that only you can execute: Pilot's most successful marketing campaigns leveraged their unique position and expertise. Their Delaware franchise tax campaign exemplified this - they identified when scary tax letters would arrive, provided genuinely helpful education, and offered free assistance. Daher emphasized: "The things I like the most are when we have gotten very into the mind of the buyer to ask genuinely, what do they care about and how can we help them?" B2B founders should develop marketing strategies that leverage their unique insights and capabilities rather than generic approaches any competitor could copy. Stay customer-proximate even as you scale: Despite Pilot's growth, Daher still personally responds to customer emails and participates in sales calls. He sold the first 100+ accounts himself and continues staying close to customers. "I think it is tempting to believe, oh, I just hire the head of sales and I hire the marketing and like they'll just go and figure it out...I think that's a huge mistake." For B2B founders, maintaining direct customer contact prevents developing an outdated understanding of buyer needs and market dynamics as the company grows. Embrace tech-enabled services over pure software: While the market favored pure software solutions, Pilot chose a hybrid model combining technology with human expertise. Daher explained their reasoning: "I have never, ever talked to a business owner who has said like, gosh, I really want to buy accounting software. It's like, no, just like solve the problem for me." B2B founders should focus on delivering complete solutions rather than tools, even if it means accepting lower margins initially, as customers increasingly value outcomes over features. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co
