Interview with Troy Henikoff, Co-Founder of SurePayroll

5 May 2011 · 14 min
14:25

In this 2011 interview, Troy Henikoff recounts the founding and evolution of SurePayroll. The original concept was an internet‑based HR portal, but a market analysis of payroll giants ADP and Paychex revealed a larger, more lucrative opportunity. Leveraging the web to deliver payroll electronically, SurePayroll eliminated legacy costs (paper checks, call‑center reps, regional processing centers) and gave small‑business owners direct, online control. The company grew to over 30,000 customers, raised $17 million in venture capital, reached breakeven around year 4, and was sold to Paychex for roughly $115 million after about 11 years of operation. Henikoff reflects on the nature of entrepreneurship as a serial activity, the importance of an exit for investors, and the challenges of building an annuity‑based B2B business versus viral consumer models. After the sale, he founded the Chicago accelerator Accelerate, mentoring ten startups annually, providing seed capital, legal support, and intensive mentorship, resulting in multiple follow‑on fundraises and job creation. He highlights one portfolio company, TapMe, as a high‑risk, high‑reward venture.

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