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After stints in investment banking and private equity, Chris acquired System Six in July 2021, a remote accounting firm serving SMBs. He doubled the team, expanding into payroll and tax, and built a fully remote operation spanning 25+ states and 3 countries. Along the way, he's been active in the Entrepreneurship through Acquisition (ETA) community, frequently speaking at and sponsoring conferences.
In this interview, we dive into how Chris prices each client relationship, the team structure behind his high-margin model, and the role technology plays in scaling advisory services. We also cover his thoughts on AI, margin compression, retention, and the recent surge in consolidation hitting the accounting industry.
Some takeaways:
You rarely need a CPA. Despite having a background in finance, Chris doesn’t hold a CPA license. He shared that it’s a common misconception that you need to hold a CPA to acquire and own an accounting firm. The two main instances that do require a CPA majority owner are if the firm uses “CPA” in its name or if the firm provides audit and attest work.
Paid discovery filters out tire kickers. System Six charges a few hundred dollars for a financial assessment as part of the sales process. The fee covers time spent analyzing a client’s books but more importantly ensures they weed out folks prioritizing cost over quality. Chris wants to focus on clients who value responsiveness, team redundancy and deep expertise in service businesses.
Expanding within your customer base. The number of new customers each month hasn’t changed much since the acquisition 4 years ago. What has changed is the number of services that a given client is using. By bundling bookkeeping, payroll, invoicing, and bill pay together, System Six improves margins and increases stickiness.
Recognizing what a remote-first culture means. Rather than trying to replicate an in-person experience with a remote team, Chris leans into the benefits of remote. This is what attracts great talent to their team. They still have team huddles and 1:1’s, but they’re not trying to host remote happy hours or require frequent meetups.
Every client gets a 3-person team. Unlike solo bookkeepers, System Six assigns each client a junior, mid-level, and senior staff member. The result is resilience, better handoffs, and a smoother client experience—especially during transitions or turnover.
AI won’t replace advisory relationships. While automation tools can accelerate onboarding and bookkeeping workflows, Chris believes small business owners will always need a real person to explain financials and advise on decisions. The difference will be the speed and breadth of what they can help on.
Red flags for an accounting firm. For those thinking of buying an accounting firm, Chris recommends doing diligence on the customer base. Are they all on Quickbooks Desktop? Do they enjoy stopping by the office to drop off documents? Questions like these help you diligence whether the business can evolve and you can actually achieve margin expansion with technology and modern systems.
Where to find Chris and System Six:
LinkedIn: https://www.linkedin.com/in/chris-williams-68057029/
Website: https://systemsix.com/
In this interview, we discuss:
0:00 Where System Six Sits in the $150B Accounting Market
1:06 Intro to Chris Williams
1:56 Running a People Business
3:33 Revenue Breakdown
5:09 Pricing and Margins in Accounting
8:30 Competing with Offshore Providers
10:37 Client Growth
12:18 Handling Scope Creep
14:27 Building a Strong Remote Culture
16:10 State-specific Regulations
19:12 Scaling an Accounting Firm
21:21 AI's Impact on Financial Services
24:24 Consolidation & the PE Roll-up Trend
27:09 Advice for those Buying an Accounting Firm
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