Anne (last name not stated)·September 20, 2022

Not Just a Young Man's Game: Acquiring at 60

Anne, a former co-managing partner of a leading Toronto law firm, acquired Agency Employment Services (AES) at age 60 after a decades-long legal career, making her an unusual searcher: late-career, female, and Canadian. AES is an HR services, PEO, and temporary staffing firm with 15 employees and three offices west of Toronto, generating EBITDA in the low end of the $1–2M range. The deal was structured with a Canadian bank loan, a vendor take-back (seller note), and equity raised through an established investor network including the HBS-affiliated CommunityETA student fund, co-led with a self-funded searcher named Jeremy from Succession Capital who provided deal experience and investor access in exchange for an equity stake. Anne was motivated by the desire to lead another growth phase rather than retire, and she drew explicit inspiration from Ruth Bader Ginsburg's post-60 career impact. Her thesis rests on PEO being underpenetrated in Canada relative to the US, a durable need for outsourced HR compliance, and cross-border demand from US companies managing Canadian workforces. The episode doubles as a case study in the advantages older, well-networked professionals can bring to search — credibility, deal flow through professional networks, and access to capital — while also highlighting Canada-specific structural differences like share-purchase norms and the absence of SBA-style financing.

Deal facts

multiple: ~4x EBITDA (illustrative range 3-5x discussed)
sde ebitda: low end of $1-2M EBITDA range (exact figure not disclosed)
financing structure: Bank loan (~2-3x EBITDA) + seller note (vendor take-back, up to ~50% of equity gap) + equity from search-fund investors and personal network; no SBA (Canadian deal)
notes: 15 employees; 3 offices west of Toronto; share purchase structure (not asset purchase, common in Canada); co-investor Jeremy (self-funded searcher via Succession Capital, Vancouver) holds equity; HBS-affiliated student investor group CommunityETA also invested

Why this business

Anne was drawn to AES because it sat at the intersection of HR, employment law compliance, and talent — areas where she had deep expertise from decades as a managing partner at a Canadian law firm. She saw the PEO model as underpenetrated in Canada relative to the US, saw durability in the baseline need for HR services, and believed she could move the business up the value chain with more premium HR offerings. The opportunity came through her network (partner Mario Nigro) and the business fit her target size range of $1–2M+ EBITDA.

What's working

Strong team of four managers who were brought into the transition by the sellers and were enthusiastic about new ownership focused on growth
Existing PEO/employer-of-record service line is an underpenetrated model in Canada with clear US precedent to follow
Cross-border opportunity: US companies with Canadian workforces that need Canadian HR compliance support
Co-investor and search partner Jeremy provided experienced guidance on financial modeling, commercial due diligence, and investor network, significantly de-risking the process for a first-time buyer
Professional network and established credibility allowed Anne to source bank financing referrals and investor introductions without heavy cold outreach

What's hard

No SBA equivalent in Canada; bank financing relies on personal relationships and credit analysis of the business rather than a standardized government-backed program
Canadian deals typically structured as share purchases rather than asset purchases, carrying more liability risk for the buyer
Commuting to three offices west of Toronto from the city — a significant lifestyle change from her prior office environment
Still early days at time of recording; all growth hypotheses (PEO expansion, premium HR services, cross-border clients) are still being tested
Search ecosystem less developed in Canada — fewer known lenders, fewer experienced advisors, less of an established community

Notable quotes

I feel like we should not have this attitude that okay well once you're past 60 you're slowing down and you're winding up — like you can do that but you know you don't necessarily need to feel like I'm not relevant anymore and I don't have something to contribute.

Everything that we know about her and the career impact that she had is all post 60 and I felt like that is something that I want — I don't want to you know I and I feel like we should not have this attitude that okay well once you're past 60 you're slowing down.

I don't think you need to feel like it's a young man's game — although I say this a couple of months into it.

I have a good feeling about this business — it's there's lots of lots of opportunities just based on what I see and my own judgment and kind of what I've experienced in my world of dealing with people and hiring and legal employment issues.