Nick Smith isn’t your typical tech founder. Hailing from Kansas City—a burgeoning football hub, not exactly a Silicon Valley—he developed and bootstrapped Sailes, an AI-native sales prospecting platform, from an idea in 2018 to a solution used by industry giants. Along the way, Nick brought his Midwestern charm and a laser focus on solving a real problem: the inefficiency of manual tasks in prospecting. Nick spoke to Valor investors and founders recently at VC DAY, Valor’s annual investor and founder conference. Valor led Nick’s seed round and since then, he’s attracted more significant capital in subsequent rounds. You can catch highlights of his conversation with Valor managing partner Lisa Calhoun below.
Revolutionizing Prospecting with Hyper-personalized AI
“Everyone thought I was crazy at first,” Smith recalls, “but the market has spoken.” Sailes isn’t just another sales tool—it’s a fully autonomous, personality-driven AI companion built to transform the way sales teams prospect. It’s like having a tireless, hyper-efficient clone of your best salesperson working around the clock.
Lessons Learned Going from Startup to Scale Up
Now raising his Series B, Smith’s journey offers valuable insights for both founders and investors. For founders, he emphasizes the importance of understanding your target market. Sailes initially targeted smaller companies but found its sweet spot with larger enterprises struggling to scale their sales efforts without scaling headcount.
“What surprised me was the enterprise need,” Smith admits. As large organizations grappled with high turnover and inefficiencies in sales, Sailebots proved invaluable, offering a solution that not only streamlined prospecting but retained institutional knowledge, making future hires more effective.
Nick also stresses the importance of building genuine relationships with investors. “It’s not just a sales process, it’s a courtship,” he says, highlighting the need for mutual trust and shared vision.
Investor Lisa Calhoun, who led Sailes’ seed round, was originally drawn to Smith’s passion for empowering sales teams. “You love to close, and you like to see closers closing,” she observes. She appreciated how Sailes frees up salespeople to focus on building relationships and sealing deals. “Many sales automation platforms turn closers into keyboard data entry cowboys–and that’s a waste of money and talent,” she said.
Sailes’ rapid growth and partnerships with major corporations demonstrate the power of AI when applied to a genuine market need.
The Future of Sales: AI-Enhanced, Human-Centered
So, what’s next for Sailes? Integrations and expanding its capabilities are key priorities. Smith envisions a future where AI not only automates prospecting but also provides valuable insights and intelligence to sales teams.
In a world where everyone seems to be slapping an “AI” label on their product, Sailes stands out by delivering real results, not just buzzwords. It’s a testament to the power of combining AI with a deep understanding of the sales process and a genuine passion for helping salespeople succeed.
As Smith puts it, “We’re not just selling widgets; we’re multiplying the impact of your best people.” That’s a pitch any investor or founder can get behind.