After two decades helping private-equity-backed and founder-led companies hire CFOs and Controllers, I’ve seen one truth hold steady:
Every business eventually outgrows the way it does accounting.
And right now, Artificial Intelligence is accelerating that moment, especially in the lower-mid and mid-market.
These companies sit in a unique place: complex enough to need sophisticated insights, but lean enough that they can’t afford armies of analysts or long technology cycles.
That’s exactly where AI-driven accounting, and the next generation of talent behind it, steps in.
Lower-Mid Market ($25M–$150M): Lean teams, manual workflows, and a few key people holding institutional knowledge. AI offers leverage by automating close, reconciliation, and payables so the same three-person team can perform like ten.
Core Mid-Market ($150M–$500M): More systems and data, but still fragmented. AI offers intelligence by surfacing insights across ERP, CRM, and banking platforms to forecast, model, and plan with confidence.
Different pain points, same outcome: both tiers need finance leaders who can connect automation to strategy.
That’s the gap the AI Accounting Strategist fills.
This emerging role isn’t science fiction. I’m already seeing it in searches.
They’re Controllers and CFOs who:
They blend finance, technology, and business acumen, and that’s what separates companies that simply automate from those that actually accelerate.
For the Lower-Mid Market: AI restores capacity. It lets small finance teams scale without adding headcount. It stabilizes processes, reduces error risk, and improves visibility.
For the Mid-Market: AI creates clarity. It connects disparate systems, delivers real-time dashboards, and turns the finance function into a predictive engine for the business.
Together, these shifts redefine what it means to have a modern finance function.
It’s not about replacing people. It’s about freeing them to think, analyze, and lead.
In both market segments, the path forward is the same:
This evolution isn’t a technology problem; it’s a talent opportunity.
AI will not replace accountants. But it will reward the companies that learn to combine automation with human intelligence.
For lower-mid market companies, that means doing more with less.
For mid-market companies, it means seeing farther and acting faster.
After 24 years in executive search, I’ve seen how the right hire can shift a company’s trajectory. And as AI reshapes finance, that next transformative hire may not be a traditional CPA. It may be an AI Accounting Strategist who brings both precision and prediction to the table.
Believe in what’s possible when intelligence meets accounting.
Which side of the mid-market are you on… building capacity or building clarity?
