Westport Town Retirement System

Westport Town Retirement System

The Westport Town Retirement System administers retirement benefits for municipal employees of Westport, Connecticut. Finance Director Gary Conrad handles day-to-day management as part of the town's broader financial operations, while investment decisions run through the Pension Investment Committee under the purview of the Board of Finance. First Selectwoman Jennifer Tooker oversees the administration that supports the fund. The system's investment strategy concentrates heavily on secondary-market transactions within private markets. This approach favors acquiring limited-partnership interests from sellers seeking liquidity rather than committing to blind-pool primary funds — a posture that can accelerate capital deployment and reduce the J-curve effect common in institutional private-equity programs. The fund also maintains allocations to cash, cash equivalents, and certificates of deposit held within Connecticut, suggesting a meaningful liquidity sleeve alongside the alternatives book. Team composition reflects the layered governance typical of Connecticut municipal pensions. The Board of Finance — whose members have included Danielle Dobin, Jeff Hammer, Brian Gaines, Liz Heyer, Rich Hightower, Allyson Stollenwerck, and Elaine Whitney — provides elected oversight. This structure means investment decisions carry political as well as fiduciary dimensions, a characteristic shared by similarly sized New England town retirement systems. What distinguishes this pension is the concentration risk deliberately assumed by stacking its alternatives program into secondaries — a strategy that is operationally lighter for a small-staffed municipal plan but demands sharp pricing discipline. The absence of a dedicated internal investment team means external consultants or managers likely drive manager selection and transaction execution, making the gatekeeper relationship unusually influential relative to larger public funds.