Inurtech: Pie Insurance Continues Leadership Team Expansion with Key Appointments

Pie Insurance, an Insurtech specializing in workers’ comp insurance for small businesses, announced it appointed leadership team members “including David Samuels as the first chief commercial officer, Dimitrius King as the first chief claims officer, Kelly North as vice president of business development, and Jen Straus as the first vice president of people operations.”

As noted in an update shared with CI, Pie also “appointed insurance veteran Laura Bishop to the company’s board of directors.”

These executives will “apply their valuable experience to help lead Pie in its next phase of growth.”

Samuels joins Pie “after nearly a decade at SAP/Concur, where he most recently held the position of chief customer officer.”

As Pie’s first chief commercial officer, Samuels “is responsible for setting Pie’s operational strategy and overseeing all premiums generated from our insurance agents and brokers.”

As Pie’s first chief claims officer, King “is responsible for leading and implementing the company’s claims strategy.”

He joins Pie most recently from Liberty Mutual, where he “was a vice president of the workers’ compensation division.”

North joins Pie as vice president of business development, “overseeing the team responsible for growing and maturing the company’s insurance agency channel.” Prior to Pie, she “spent two years at Beam Dental as the company’s vice president of business development.”

Straus “is responsible for Pie’s compensation, benefits, people operations and analytics, as well as learning and development.”

She joins the company with “a wealth of people operations experience at hyper-growth startups, including Kabbage and Alteryx.”

In addition to the new leadership team hires, Pie “added Laura Bishop to its board of directors.”

Bishop brings nearly 40 years of executive leadership experience “at publicly traded and privately held companies, including almost 20 years at USAA, most recently as its chief financial officer.”

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

“We are honored to have these exceptional leaders join our team of nearly 400 passionate and mission-driven Pie-oneers. These leaders are the best at what they do and are uniquely positioned to help us continue on our journey of making insurance less expensive, simpler, and more transparent for small business owners.”

Pie continues to “expand its team of talented Pie-oneers across the country.”

As covered, 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 $300M in funding and commitments for future funding, grown its gross written premium to over $100M, and partnered with over 1,000 agencies nationwide.”



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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 - Oct 24, 2026 vs Jan 1, 2025 - Oct 24, 2025

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Number of Filings131Prior 126 +4.0%
Target Raise, Total$3.40BPrior $3.54B -3.9%
This YTDYear priorChange
Filings 131 126 +4.0%
Target raise $3.40B $3.54B -3.9%

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