Chris Williams·January 12, 2023

System Six: One Year Update | Chris Williams Interview

Chris Williams is a former finance and PE professional (MBA) who acquired System Six, a remote bookkeeping and financial back-office services firm, in July 2021 via a self-funded SBA deal with a small investor group. This is a one-year update episode recorded roughly 14 months post-close. Revenue grew from $2.5m to ~$3.7m and headcount from 18 to 31, though EBITDA margins compressed as the management layer was built out. The business serves small businesses generally but has found a strong niche in the search/ETA community, where Chris's credibility as a former searcher drives referral-based growth. Key lessons shared include getting in front of top customers immediately post-acquisition, finding leadership voice early rather than defaulting to deference, and the structural tension of scaling a people-dependent professional services firm. Chris reflects candidly on the self-funded vs. traditional search trade-off — arguing self-funded raises the floor but lowers the ceiling — and on the difficulty of building a sales function to replace himself as the primary seller.

Deal facts

multiple: lower multiple (self-funded SBA, no specific multiple stated)
sde ebitda: ~$1m EBITDA at acquisition; ~10% EBITDA margin on ~$3.6-3.7m revenue at time of interview
revenue: $2.5m at acquisition; ~$3.6-3.7m at time of interview
financing structure: SBA loan + seller financing + investor equity (self-funded search with a small number of investors, no traditional search fund capital)
notes: Acquired July 2021; ~18 employees at acquisition, ~30-31 at time of interview; remote business; W-2 US-based staff

Why this business

Bookkeeping is a massive, growing market with mission-critical service, strong working capital dynamics (weekly billing), relatively low customer acquisition cost, and a premium positioning opportunity. The remote nature fit his Bay Area lifestyle. He also saw the search/ETA community as an underserved niche customer base he could sell into directly.

What's working

Revenue grew from $2.5m to ~$3.6-3.7m in ~14 months, adding 12+ staff to reach 31 people
Selling into the search/ETA community has become a strong channel — ~15 search-acquired businesses now as clients, pushing up average customer size and service depth
Consultative, trust-based sales process with 130 sales calls in year one proved effective despite no prior formal sales experience
Strong organic growth opportunity reducing urgency of M&A; organic growth has fewer integration headaches
Culture built by prior owner (team-first focus) was an asset carried forward and doubled down on
Board structure with 3-4 active investors provides strategic accountability and perspective across multiple businesses
Created head-of-people role promoted from inside to focus on retention and recruiting

What's hard

EBITDA margin compressed significantly — revenue up ~30-48% but EBITDA only up ~10%, due to management layer costs and owner salary
Hiring quality has degraded in Q4 2022 — top-of-funnel applicant quality on Indeed and LinkedIn declining despite increased spend
Business scales linearly with headcount, creating a hard constraint on growth
Chris is still the primary salesperson, creating a bottleneck — building out a dedicated sales function is overdue
Did not get in front of top customers quickly enough post-acquisition — lost at least one customer that better relationship management might have retained
Finding his voice and asserting leadership early was harder than expected; was overly deferential at first
Pricing pressure from offshore providers and low-cost competitors requires deliberate premium positioning

Notable quotes

If you do self-funded deal you raise your floor... but I also think that you lower your ceiling if you do an SBA deal. There's Searchers out there in traditional that buy a 10 million EBITDA or six million dollars of EBITDA and if they double that business in five years you know just in terms of their career development their financial outcome that's probably a higher ceiling.

Get in front of customers faster. I was a little... very much wanting to sort of structure a lot of what I did based on feedback I was getting internally but some of the feedback internally was like hey you getting out in front of our top 20 customers introducing yourself sort of saying there's been a transition might cause some disruption — I think that was absolutely a mistake.

I would have found my voice earlier. I think I was very much out of the gate trying to be extremely deferential — and that's helpful — but like if there's things that I see that I want to have happen like just push it, push it. You are ultimately the leader of the organization.

Our business only scales as much as we're able to hire and retain fantastic people and that's our number one mission and has to be — like trying to build a great place to work first and foremost.