Building a Tech-Enabled Bookkeeping Empire: Lessons from Chris Williams

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.

Episode Highlights:

[02:48] Chris's background and decision to acquire System Six
[06:47] Growth and scaling challenges since acquisition
[09:54] Insights on hiring for sales and marketing roles
[12:02] The importance of the search fund and independent sponsor community for client acquisition
[23:08] Detailed explanation of the "pod" structure for service delivery
[30:26] Long-term vision for expanding services and scaling to $50 million
[32:15] Exploration of offshore talent and automation in bookkeeping services
[38:55] Key lessons learned about delegation and employee development

Quotes:

"When I discovered the path of like, 'Hey, look, you can go buy your own small business and grow and run it yourself,' I mean, to me, that is like the most go deliver results or not. It's all on us in the leadership seat in these small organizations."
"Everything we have to do here at System Six is first about, 'Hey, what's the best thing for our team members?' Because they're our business. So we kind of have to optimize for them first."
"The long-term goal is a one-stop shop for recurring professional services to small businesses."
"As much as you know, you want to grow and go work on new things to cross-sell or everyone wants to do M&A... make sure if you're gonna hand stuff off to your team, that they're actually prepared to do it well. Give them a chance to succeed."

Episode Resources: