Insurtech: Pie Insurance Announces New Hires of VP of Underwriting, VP of Claims Operations, Others

Pie Insurance, an Insurtech company specializing in workers’ comp insurance for small businesses, recently appointed three strategic leadership team hires:

  • Rick Poulin, vice president of underwriting
  • Joshua Brost, vice president of marketing
  • Sam Elizondo, vice president of claims operations.

These “pie-oneers” join Pie after “a series of company milestones including raising a $315M Series D round of funding and will bring fresh perspectives and a passion for serving small businesses as Pie continues to carve its path as a leader in the small business commercial market.”

As vice president of underwriting, Poulin is “responsible for overseeing the company’s business planning, forecasting, and loss and expense management.” Poulin brings the team “more than 20 years of experience in the insurance industry, including more than a decade at Travelers, where most recently, he was the company’s vice president of workers’ comp.”

Brost joins Pie “with nearly 20 years of experience focused on building integrated and data-driven marketing teams at both startups and large enterprises.”

As the company’s vice president of marketing, he oversees “all department functions including direct marketing, partner marketing, public relations, brand, lifecycle marketing, media, and talent branding.” Prior to Pie, Brost “led digital and integrated marketing at Bolt, and led the growth and integrated campaigns team within the Modern Work marketing organization at Microsoft.”

As vice president of claims operations, Elizondo is “responsible for building out our quality, shared services, training, contact center, and special investigations unit.” Elizondo brings over 17 years of experience in the financial industry, “including various positions within the claims space including personal and commercial lines in both the property and casualty and group benefits space at The Hartford Insurance company.”

John Swigart, co-founder and CEO of Pie, said:

“I’m thrilled to have these three leaders join our team during a pivotal time of growth for our company. Their experience building winning teams combined with their passion for small business are instrumental in Pie driving towards our mission of enabling small businesses to thrive by making commercial insurance affordable and as easy as pie.”

Poulin, Brost and Elizondo join “a growing leadership team of technology, business and insurance industry veterans including recent appointments of Ekta Aggarwal as the company’s chief product officer and Erin Mesick as vice president of finance.”

Pie Insurance is “leveraging technology to transform how small businesses buy and experience commercial insurance, with the goal of making it affordable and as easy as pie.”

Pie’s intense focus “on granular, sophisticated pricing, and data-driven customer segmentation enables Pie to match price with risk accurately across a broad spectrum of small business types, which allows Pie to offer more affordable insurance to small business owners.”

Since 2017, Pie has “received over $615M in funding and partnered with over 2,800 agencies nationwide.”



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Disclosure Quest

Reg A - Form 1-A Filings Beta

Beta. Initial Form 1-A only. Target raise is the stated Amount to be Raised, totaled. Compared with the same dates one year earlier.

YTD: Jan 1, 2026 - Nov 4, 2026 vs Jan 1, 2025 - Nov 4, 2025

Share this graph
Number of Filings134Prior 129 +3.9%
Target Raise, Total$3.45BPrior $3.59B -3.8%
This YTDYear priorChange
Filings 134 129 +3.9%
Target raise $3.45B $3.59B -3.8%

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Source: DisclosureQuest. Initial Form 1-A only.

Created by Crowded Media Group

This display counts initial Form 1-A filings only. It does not represent subsequent filings, including Form 1-A/A amendments or Form 1-A POS post-qualification updates filed by the issuer. Amounts are the stated Amount to be Raised on the initial filing, not capital raised and not amounts revised in later filings.

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