#30: How Gusto’s CEO Built a Category-Defining Company - Leadership, Scaling & Long-Term Growth

Overview

Josh Reeves, co-founder and CEO of Gusto, shares his insights on building a category-defining company that supports small businesses. The conversation explores sustainable growth, navigating regulatory challenges, fostering a customer-first culture, and the leadership principles that have guided Gusto’s journey. Reeves emphasizes long-term thinking, disciplined execution, and the importance of creating meaningful impact for customers and employees alike.

Notable Quotes

- Go fix something, go make it better. Work is fundamentally about going and fixing or making something better for your teammate, your customer, or your business. – Josh Reeves, on the purpose of work.

- Our goal is to grow as fast as we can with three checks and balances: product quality, unit economics, and employee experience. – Josh Reeves, on sustainable growth.

- Work done right is about helping people. That’s what I tell my kids when I leave for the office. – Josh Reeves, on the meaning of work.

🚀 Building for Long-Term Growth

- Reeves outlines Gusto’s growth strategy, emphasizing sustainable scaling over hypergrowth.

- The company focuses on three key metrics: product quality, unit economics, and employee experience.

- Gusto prioritizes compounding growth by maintaining high standards in customer satisfaction (e.g., NPS) and reinvesting profits into product development.

- Reeves critiques startups that gamble on unsustainable business models, advocating for disciplined financial management.

📜 Simplifying Regulatory Complexity for Small Businesses

- Reeves highlights how regulatory burdens disproportionately affect small businesses, often leaving them unable to access benefits like tax credits or 401(k) plans.

- Gusto’s products aim to automate and simplify compliance, enabling small businesses to unlock financial incentives and focus on growth.

- He describes the fragmented nature of U.S. regulations, likening it to operating in 50 different countries, and stresses the need for streamlined processes.

💡 Leadership and Culture at Gusto

- Reeves emphasizes the importance of hiring for a growth mindset, seeking individuals who are curious, experimental, and resilient.

- Gusto fosters a culture of productive discontent, encouraging employees to challenge the status quo and continuously improve.

- Leadership at Gusto is grounded in authenticity, with Reeves urging employees to be yourself and focus on solving customer pain points.

🤖 Embracing AI and Experimentation

- Reeves discusses how Gusto integrates AI to enhance customer experience and streamline operations, such as automating payroll processes.

- He values a culture of experimentation, where employees are encouraged to test new tools and approaches, even if initial attempts fail.

- Reeves advises grounding AI adoption in customer impact, ensuring that technology serves to improve user outcomes.

🌱 Personal Values and Family Lessons

- Reeves shares how his family values—curiosity, generosity, kindness, and resilience—shape his leadership style and personal life.

- He reflects on the importance of gratitude and staying grounded, using daily reflections to reinforce these values with his children.

- For Reeves, success is measured by how helpful he is to others, both professionally and personally, rather than by recognition or accolades.