CORRECTED-Exclusive: Cowbell chief claims officer Le to exit Zurich-backed insurtech

By James Thaler

March 5 - (The Insurer) - Cowbell’s chief claims officer Theresa Le has resigned from the insurtech after three years with the company, following a number of other senior departures from the firm over the last nine months, including its CUO, CFO and CMO.

According to sources, Le’s last day with Cowbell will be Friday March 7. It is understood that the executive is weighing a number of options and plans to take some time to make a decision regarding her next employer.

A spokesperson for Cowbell confirmed Le's departure in a statement to Cyber Risk Insurer.

"Theresa Le was foundational in building our world-class claims organisation over the past three years and we wish her all the best. We look forward to sharing her replacement soon," the company said in a statement.

Le originally joined Cowbell in January 2022 as head of claims and risk engineering, before being promoted to chief claims officer in November of that year.

She previously worked for brief stints in cyber claims roles at Swiss Re and Axa XL, as well as at law firms Clyde & Co, Atheria and Duane Morris.

Le’s departure is the latest exit from Cowbell’s senior ranks in the past year, after the resignations of chief underwriting officer Caroline Thompson and chief financial officer Dave Junius in September, and of chief marketing officer Andrea Collins in October.

In November Cyber Risk Insurer reported the departures of Western regional VP sales and distribution leader Michael Bibeau, Southwest senior territory manager Gabe Karroum, director of product marketing Julie Longmire and account executive for programs and affinity business, Maggie Schneider.

Cowbell’s chief commercial officer Dan Law and chief strategy officer Matthew Jones both also left the company last year.

Four of the departed senior executives – Junius, Law, Jones and Collins – were direct reports of Cowbell founder and CEO Jack Kudale.

In January Cowbell announced it had hired former Sayata executive Tim Regilio as its new Western US territory head and in October announced that it had hired Denise Pagliarulo from Axis as SVP and head of finance and promoted Eric Biderman to general counsel.

In November Cowbell also promoted Thomas Pytel to VP and head of marketing.

Cowbell sealed a $60 million Series C funding round with Zurich Insurance in July 2024 which valued the insurtech somewhere around $400 million. The Insurer reported in August that the deal with Zurich includes a provision that gives the Swiss insurer the right of first refusal to acquire the insurtech in its entirety, under certain conditions.

According to sources, Cowbell wrote around $170 million in premium in 2023, meaning the latest funding round has valued the insurtech at more than two times written premium.

Cowbell had begun work on the fundraise in early 2023 with an initial goal of raising $100 million for its Series C, before securing $25 million in a so-called “Series B top-up” in November.

That raise brought in new investor Prosperity7 Ventures, a $1 billion venture fund that is a subsidiary of Saudi Arabian oil giant Aramco.

The insurtech has also undertaken at least two significant rounds of layoffs in the past year and a half.