Joshua Reeves, the CEO and co-founder of Gusto, has built a company that’s transforming how small and medium-sized businesses (SMBs) manage payroll, HR, and benefits. Since founding Gusto in 2011, Reeves has led the company from a modest startup to a fintech giant valued at $9.6 billion, serving over 300,000 businesses across the United States. His journey reflects a blend of technical expertise, values-driven leadership, and a relentless focus on solving real-world problems for entrepreneurs. This article explores Reeves’ background, his vision for Gusto, and the principles that have guided his leadership.
Early Life and Foundations
Born and raised in the San Francisco Bay Area, Reeves was shaped by a diverse range of influences. His mother, a Bolivian immigrant, and his father, from a steel mill family near Pittsburgh, were both teachers, instilling in him a respect for hard work and education. As an Eagle Scout, Reeves developed an early sense of discipline and a strong commitment to community service. A pivotal moment came in fifth grade when a teacher’s feedback during a parent-teacher conference sparked his academic focus. By high school, he transformed from an out-of-shape teen into an athlete, embracing teamwork and collaboration—traits that would later define his leadership style.
Reeves pursued electrical engineering at Stanford University, earning both a bachelor’s and a master’s degree. At Stanford, he was a Mayfield Fellow and received the Terman Engineering Award, honing his problem-solving skills and entrepreneurial mindset. His early career included a stint at Zazzle, followed by the co-founding of Unwrap, a SaaS startup that was acquired in 2010. These experiences laid the groundwork for his next venture: Gusto.
The Genesis of Gusto
The idea for Gusto (originally ZenPayroll) emerged from Reeves’ frustration with inefficient payroll and HR systems while running Unwrap. Alongside co-founders Edward Kim and Tomer London, Reeves saw an opportunity to simplify the complex, often impersonal processes that burden small business owners. Launched in 2012 after graduating from Y Combinator, Gusto aimed to make payroll, benefits, and HR seamless and human-centric. Reeves describes the mission as creating “a world where work empowers a better life,” a vision that continues to drive the company.
Gusto’s early days were marked by a “no shoes” office policy, a nod to Reeves’ upbringing in a shoe-free household. This quirky tradition started in a Palo Alto bedroom and persisted as the company grew, symbolizing Gusto’s commitment to authenticity and comfort. By 2015, Gusto expanded beyond payroll to include benefits and compliance services, rebranding from ZenPayroll to reflect its broader scope. Today, it’s a comprehensive platform that processes hundreds of billions of dollars in payroll and partners with major players like JPMorgan Chase.
Values-Driven Leadership
Reeves’ leadership philosophy centers on alignment—between company values, employee motivations, and skill sets. He interviewed Gusto’s first 60-70 hires, ensuring cultural fit. As the company scaled to 2,500 employees, he implemented a structured hiring process with peer shadowing and training to maintain this alignment. Reeves emphasizes that while skills are critical, shared values and passion for Gusto’s mission are non-negotiable.
Gusto’s culture is famously unique, from nature walks for big decisions to a “no shoes” office vibe. Reeves fosters an environment where kindness and competitiveness coexist, encouraging employees to think critically about SMB challenges. During the COVID-19 pandemic, Gusto enabled $2.5 billion in Paycheck Protection Program loans, showcasing its commitment to supporting small businesses in crisis.
Reeves’ role has evolved from hands-on founder to strategic steward. He relies on tools like Objectives and Key Results (OKRs) and regular business reviews to keep Gusto’s teams aligned. By empowering leaders with autonomy while ensuring cohesive direction, Reeves has scaled Gusto without losing its mission-driven core.
Challenges and Tough Decisions
Leading a high-growth company hasn’t been without challenges. In 2023, Reeves made the difficult decision to lay off 126 employees (5% of Gusto’s workforce) to navigate economic uncertainties. In an email to staff, he expressed regret and outlined generous severance packages, including COBRA coverage, equity vesting adjustments, and an alum talent directory to support those affected. This transparency and care reflect Reeves’ belief that even tough decisions should align with Gusto’s people-first values.
Fundraising for an SMB-focused SaaS company also posed early hurdles, as investors often favored enterprise or consumer markets. Reeves overcame this by highlighting the massive potential of the SMB segment and Gusto’s ability to deliver meaningful impact. Backed by top-tier investors like General Catalyst, Kleiner Perkins, and Y Combinator, Gusto raised over $500 million, fueling its growth.
Looking Ahead
Reeves envisions Gusto as a multi-decade company that outlives him. A key part of this vision is Gusto Embedded, a strategy to integrate payroll and HR solutions into platforms that small to medium-sized businesses (SMBs) already use, such as Chase Payment Solutions. This approach, inspired by fintech leaders like Stripe, aims to streamline user experiences and scale Gusto’s impact.
For aspiring entrepreneurs, Reeves offers practical advice: obsess over a problem, build for the long term, and prioritize cultural alignment. He views fundraising as akin to hiring and seeking investors who share the company’s mission and values. His journey—from Stanford grad to unicorn founder—underscores the power of persistence and purpose.
Conclusion
Joshua Reeves’ leadership at Gusto exemplifies how a clear mission, authentic culture, and strategic focus can transform an industry. By simplifying the complexities of payroll and HR, Gusto empowers small businesses to thrive, fulfilling Reeves’ vision of work as a force for better lives. As Gusto continues to grow, Reeves remains a steward of its values, proving that empathy and ambition can coexist in building a lasting legacy.
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