Acquisition Entrepreneur

Looking for one PEO or HR services business worth running for the next decade.

I'm searching for a founder-owned regional PEO, ASO, or specialty HR services company to acquire and operate for the long term. My priority is continuity — for your team, your clients, and the name on the door.

A note to founders
General contractor and suited professional shaking hands on an active construction site with crew working in the background
6 yrs
Mercer — HR & Benefits
Yale SOM
MBA 2026

Investment thesis

Acquire and scale a PEO or HR outsourcing business built for the trades.

Combine stable, recurring PEPM revenue with the upside of workers' comp underwriting and safety-driven loss reduction in a market with significant white space. Every small business benefits from outsourced HR, but contractors and building services firms benefit the most: their workers' comp exposure is elevated, their experience mod can swing hard in one bad year, and risk pooling with disciplined safety management turns that volatility into an advantage. $414B industry, 4.5M worksite employees, ~9% projected CAGR, and still under 15% penetration among eligible 10 to 99 employee firms.

Thesis

A durable business model in a fragmented market.

The characteristics that make a well-run PEO or ASO an exceptional acquisition target are the same ones that make it a great business to run for the long term.

01
Revenue scales with client success
PEPM billing means when a client hires, revenue grows automatically. No renegotiation, no new contract. A contractor who scales from 18 to 26 workers pays the PEO over 40% more — while cost-to-serve stays nearly flat.
02
Embedded in the operations stack
A well-run PEO becomes part of the fabric of how a client runs: payroll, benefits, workers' comp, and HR workflow all routed through a single partner. That integration is what makes the relationship durable: clients grow faster, stay longer, and the cost of leaving rises every year they're on the platform.
03
Earned margin, not commodity margin
Margin in this business comes from discipline: client selection, claims management, benefits plan design. A well-run book produces outcomes the mass market can't replicate. That's a durable advantage, not a spreadsheet assumption.

Value creation

AI initiatives with a clear path to sustainable growth.

Three concrete opportunities to modernize the operating model without disrupting what already works. Each targets a specific economic lever: inbound lead generation, claims cost reduction, and medical spend management.

01
AI-assisted local SEO at scale
Hundreds of locally optimized pages built at a fraction of agency cost, generating an inbound lead channel that doesn't exist in this segment today.
02
Predictive risk scoring on the claims book
A model that flags the accounts most likely to generate losses, directing safety audits and underwriting attention before injuries occur rather than after.
03
AI claims triage layer
Automated severity scoring, fraud flagging, and medical provider steering on every claim as it comes in, compressing cycle time and holding down loss costs.

Background

Tom Ryan
Six years inside the employer services ecosystem at Mercer

Mercer is a Marsh McLennan subsidiary operating across 130 countries in benefits design, actuarial consulting, HR technology, and workforce strategy for large employers.

What Mercer builds bespoke for Fortune 500 clients — plan design, carrier negotiation, compliance infrastructure, risk management — a well-run PEO packages into one product for small employers who can't build it themselves. Same underlying services, different delivery model. Six years inside that world made the PEO opportunity obvious.

  • 2024–26
    Yale School of Management — MBA
    Entrepreneurship and AI concentration. Built a proprietary PEO acquisition thesis.
  • Summer 2025
    ProGuard (Coleville Partners) — MBA Associate
    Search-acquired warranty platform with a structurally similar model: pool premiums, retain everyday claims, transfer catastrophic risk to reinsurers. Claims frequency control and aggregate stop-loss mechanics transfer directly.
  • 2019–25
    Mercer — Consultant to Account Executive
    HR technology implementation and enterprise B2B account management. $10M+ portfolio, 100+ client relationships.
  • 2015–19
    Yale University — Division I Basketball
    Two-time Ivy League Champion. Team Grit Award recipient. Hall of Fame inductee, Steady Buckets NYC (youth basketball nonprofit).
What I bring as an operator
  • Relationship-driven sales & client management experience
    Managed a $10M+ portfolio across 100+ B2B relationships at Mercer, consistently hitting quarterly targets in a long-retention, relationship-driven business.
  • PE-backed operating experience
    At ProGuard, worked inside a structurally similar risk-pool model. Claims control, reinsurance, and stop-loss mechanics transfer directly to a PEO.
  • Leadership under pressure
    Division I athletics, enterprise client delivery, and PE-backed operating work.

What I'm looking for

The right business for a long-term owner.

The right business matters more than fitting a precise box.

If yours is close, I'd like to hear about it.

Business type Regional PEO, ASO, or specialty HR services firm. Construction and trades focus preferred but not required. ASO operators and PEOs with minimal WC retention are equally of interest (the thesis works across risk profiles).
Financials $750K to $2M normalized EBITDA. Three years of tax returns are enough to begin a conversation.
Ownership Founder or family-owned. Owner considering transition within 1 to 5 years.
Deal structure Fast, flexible deal terms with a dedicated network of investors. Rollover equity, seller note, or earnout welcome. Close 60 to 90 days from LOI.

Financing

Professional agreement signing
01
Personal capital
My own money is in the equity stack. Skin in the game means my incentives are aligned with the long-term health of the business.
02
Committed investor network
Former operators and entrepreneurial capital partners who know this space. Not institutional LPs waiting on committee — they move quickly and they understand the model.
03
Access to traditional or SBA 7(a) debt
Standard acquisition vehicles with established lender relationships in the ETA space.
What this means for you
Capital is confirmed before any offer. Diligence is focused and time-bounded. No handoffs to committees, no financing surprises.

A note to business owners

You built something real. I want to take care of it.

No financing surprises
Capital is confirmed before the LOI. No committee, no waiting.
Your team stays
I'm here to learn and grow what works, not to cut.
Your name stays
The brand you built in your community is an asset worth protecting.
Stay as involved as you want
Consult, advise, or step away. Your call.
Professional conversation
Let's have a conversation.
No pressure, no formality. Just a conversation about what you've built.

If you own a PEO, ASO, or HR services business and have been thinking about what comes next, I'd like to hear from you. You don't need a decision made or a number in mind.

All conversations are confidential. If the timing isn't right today, I'll reach back out when it is.

Tom Ryan