How Josh Reeves Built a $10B Company Serving Small Businesses
EP 111 of The Logan Bartlett Show: Untold stories from tech's inner circle
Josh Reeves has built Gusto into a nearly $10B company with over $500M in ARR, serving small businesses. In our conversation, Josh delves into Gusto’s 13-year journey, sharing insights on how they achieved product-market fit by initially targeting a very narrow niche. He also highlights the tactics they’ve used to build an intentional culture of humility and helpfulness, along with lessons he’s learned in hiring executives. We also explore the future of Gusto and the opportunities that lie ahead for the business.
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✉️ Episode Memo
→ How Gusto Started By Winning a Narrow Market
At the start, Gusto focused on serving a very specific niche: new employers in California with only full-time, salaried employees and no contractors. This allowed them to create a product people loved and achieve good unit economics from day one. After proving their product's value within this narrow segment, they expanded geographically state by state, ensuring a fully featured offering for small businesses. Prioritizing depth and product completeness over rapid expansion laid a strong foundation for long-term growth.
→ Gusto’s Winning GTM Strategy
They knew combining a great product with excellent go-to-market execution was essential to capture the small business market. To do so, Gusto focused on high NPS, word-of-mouth, conversion, and retention, gradually adding content marketing and paid acquisition. By avoiding early reliance on paid growth, they ensured sustainability and expanded through diverse programs like their extensive referral network. Today, the referral program has over 17,000 accountants, but it began with just a single conversation at a conference.
→ Gusto’s VMA Interview
Initially, Josh interviewed the first 50+ hires himself, and while skills were crucial, he prioritized candidates who genuinely cared about the mission to ensure the company would continue to stand for something. As the company grew, he delegated the process to trusted team members and formalized it into a Values, Motivation, and Alignment (VMA) interview process. Now, a dedicated team conducts these interviews, ensuring that every hire fits in naturally.
A really fun conversation that I wanted to have for a long time with one of the preeminent leaders in Silicon Valley, more insights on the full episode.
⭐ Trailer
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