Covered Welcomes Industry Veteran Jerry Halbrook as President & Chief Operating Officer

DENVER, September 23rd, 2025 — Covered Insurance, a leading embedded insurance platform transforming how insurance is delivered and experienced, proudly announces the appointment of Jerry Halbrook as President and Chief Operating Officer.

With more than four decades of executive leadership across mortgage lending, banking and fintech, Halbrook joins Covered at a pivotal time in the company’s growth trajectory. His deep expertise in operational scale, innovation, and culture-building is expected to accelerate the company’s momentum toward sustainable profitability and long-term market leadership.

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Halbrook previously served in senior executive roles at Deloitte & Touche, Prudential Home Mortgage, Bank of America, and Black Knight, where he was President. He was also the co-founder of Nexstar Financial and, most recently, served as Chief Mortgage Innovation Officer at PennyMac.

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“Jerry is the steady, high-EQ, operational partner I’ve been searching for,” said Ross Diedrich, CEO and co-founder of Covered. “He brings the rare combination of strategic execution, technological innovation, and people-centered leadership. His impact will be both immediate and lasting.”

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Halbrook has a proven track record of transforming organizations through pragmatic execution and culture-first leadership. At a previous company, his rollout of a values-driven performance initiative led to top-decile culture and performance rankings within 18 months.

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“Covered’s mission to empower financial wellbeing through seamless, tech-enabled insurance aligns perfectly with my personal values and professional journey,” said Halbrook. “I’m excited to join this incredibly talented team and help scale the company’s vision in this next chapter of growth.”

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Halbrook’s appointment comes at a key moment, as Covered intensifies its focus on revenue growth and profitability following the recent addition of CRO, Dan Bos. His leadership will strengthen operational execution across departments while enabling CEO Ross Diedrich to double down on strategic partnerships and topline initiatives alongside the company’s revenue team.

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“As we navigate a rapidly evolving financial services landscape, Jerry’s ability to balance technology, data, and human-centered leadership will be instrumental,” added Diedrich. “We’re thrilled to welcome him aboard.”

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About Covered
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Covered is a digital insurance marketplace purpose-built to help lenders enhance the borrower experience and unlock new revenue streams. With flexible APIs, advanced automation, and a trusted network of top-tier carriers, Covered empowers financial institutions to seamlessly embed personalized insurance offers directly into their platforms—right when and where customers need them. Recognized by HousingWire as a Top Tech100 company, Covered transforms insurance into a strategic value-add that drives loyalty, improves close rates, and keeps borrowers engaged from application to closing and beyond. Learn more at www.itscovered.com.

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Covered Media Contact

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Michael Hammond JD, CMT

NexLevel Advisors LLC

Media Contact for

734-775-4879

mhammond@nexleveladvisors.com

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