The New Rules with Alan Pentz
Building a Tech-Enabled Bookkeeping Empire: Lessons from Chris Williams
June 25, 2024
In this insightful conversation, Alan interviews Chris Williams, founder of System Six, an outsourced finance service provider. Chris shares his journey from a finance background to acquiring and scaling a bookkeeping business. They discuss innovative organizational structures, the challenges of scaling professional services, and Chris's vision for expanding into a comprehensive back-office solution for small businesses.
The episode begins with Chris explaining his background in finance and his decision to acquire System Six in July 2021. He outlines the transition from working in private equity to running a small business, emphasizing the appeal of being directly responsible for driving results.

Chris then delves into the details of System Six's business model, providing outsourced finance services to small businesses. He discusses the company's growth since its acquisition, doubling in size to 38 people and $4.5 million in revenue. Chris shares insights on the challenges of scaling, including the strategic decision to invest in leadership infrastructure at the expense of short-term profitability.

The conversation pivots to Chris's approach to sales and marketing, highlighting the importance of distinguishing between lead generation and closing skills. Chris explains how he leveraged his experience in the search fund and independent sponsor communities to drive new business, with a focus on recently acquired companies needing finance upgrades.

A significant portion of the discussion revolves around System Six's unique "pod" structure for service delivery. Chris details how this approach benefits both employees and clients, fostering a sense of community while ensuring service continuity. He also addresses the challenges and benefits of this organizational model as the company continues to scale.

The interview concludes with Chris sharing his long-term vision for System Six, aiming to become a one-stop shop for recurring professional services to small businesses. He discusses plans for expanding into tax services, CFO services, and potentially insurance and HR consulting. Chris also touches on the company's exploration of offshore talent to address capacity challenges and the potential for leveraging industry-specific knowledge and automation to create additional value for clients.

Throughout, Chris emphasizes the importance of continuous learning, strategic delegation, and investing in employee development as key factors in successfully scaling a service business.

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