Tom Kapsimalis from CPP Investments on winning in a $220B secondaries market

Tom Kapsimalis is Managing Director and Head of Secondaries at CPP Investments, where he leads the team that buys and sells private equity stakes and continuation vehicles, deploying roughly $3–5B a year.

He has worked in secondaries since the market traded barely $10B a year; in 2025 it cleared $220B, and he has been part of that rise from the start.

Katie and Tom talk about how CPP decides where it has a real right to win, why alignment is the first thing he tests in a continuation vehicle, how a single secondary can become a years-long relationship with a manager, and where the market heads next.

His take on the "CV squared": the rationale for the deal matters as much as the price.

Tom Kapsimalis is Managing Director and Head of Secondaries at CPP Investments, based in Toronto. He leads the team responsible for the firm's private equity secondaries program — across LP-led and GP-led transactions, single- and multi-asset continuation vehicles, and structured secondaries — and oversees portfolio sales for CPP Investments' private equity department.

He began his career in 2008 in investment banking in New York, working in syndicated leveraged finance through the financial crisis, before moving to the buy side and into the secondaries market in its early days. He has been part of the secondaries business at CPP Investments through its growth from a nascent strategy into one of the largest segments of private markets, where the firm now deploys an estimated $3–5B a year.

The Re-Up is a podcast about the business of raising and allocating capital in private markets — and how that work can be done better. In private markets, a re-up is the decision to recommit to a manager's next fund: the ultimate signal of trust. Each episode is a candid conversation with the LPs, GPs, and advisors who have built exceptional track records — the conversations that usually happen over dinner after the conference, not the ones on stage. Hosted by Katie Fasken, founder of August Advisors, a Toronto-based placement firm connecting exceptional private investment managers with institutional capital.