Pie president Craig announces upcoming resignation

By Isha Marathe

Feb 14 - (The Insurer) - Dax Craig, co-founder and president of Pie Insurance has announced that he is leaving his role as president at the company in a LinkedIn post on Friday.

He plans to stay on at least for "several months" before initiating the departure, he said.

"After nearly eight incredible years, I’ve made the decision to step away from my role as President of Pie," Craig said.

"It’s been a privilege to build Pie from the ground up based on the premise that small businesses deserve better from the insurance industry. I’ve always been an entrepreneur and the time has come for me to start building something new."

The company, which launched in 2017, has had its ups and downs over the last few years, with a funding round and a budget revisions.

In May 2023, CEO John Swigart said in a message to employees that the company would be laying off 14 percent of its workforce after Pie’s leadership team identified over $25mn in annual expenses it needed to eliminate from its budget, The Insurer reported.

Incidentally, the layoffs came after Pie secured $315mn in Series D funding, more than doubling its total capital raised to over $615mn. This was the largest US P&C insurtech financing round of 2022, with Swigart telling this publication that it should be enough to secure its profitability.

In March 2024, AM Best placed under review with negative implications the A- financial strength rating and “a-” long-term issuer credit ratings of The Pie Insurance Company following “material” underwriting losses in 2023 resulting from reserve development in its New York book.

“Although reserves have stabilized since third-quarter 2023, the magnitude of the development is concerning and has had an adverse impact on Pie’s risk-adjusted capital position,” the rating agency said.

At the time, Pie management said it was implementing strategic initiatives to address the decline in its risk-adjusted capital.

In Friday's post, Craig said his decision to resign, "supported by [Swigart], the board, and our senior leadership, has been one I’ve been carefully considering for a while. While it’s not easy to leave something so deeply personal to me, I’m confident it’s the right move for me and for Pie".