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Monday, February 23, 2026
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DigitalOwl Announces the Appointment of Jennifer Richards as Vice President, Life Insurance

DigitalOwl is pleased to announce that Jennifer “JR” Richards has joined the company as Vice President, Life Insurance. JR brings a wealth of experience as an underwriting leader at three of the largest companies in the industry: Principal Financial Group, New York Life, and MassMutual. Her notable accomplishments include playing a lead role in developing Tele-Underwriting, Principal’s Accelerated Underwriting Program, the use of Electronic Health Records, and standing up Principal National, a 49-state insurance company. Her most recent role as Chief Underwriter was with Bestow, an insurtech startup working to reinvent the sales and underwriting of life insurance.

As Vice President, Life Insurance, JR will lead DigitalOwl’s growth strategy in this sector, developing meaningful relationships with life insurance carriers, reinsurers and others in the industry by demonstrating how DigitalOwl’s Natural Language Processing (NLP) platform can elevate the underwriting role by significantly enhancing and accelerating the medical records review process.

“DigitalOwl’s meaningful medical record summaries are a great tool for underwriters focused on a highly accurate yet streamlined underwriting process. Further, the data locked inside of medical records is a goldmine for carriers looking to increase their level of automation and speed to decision. I’m looking forward to working with the DigitalOwl team to bring this innovative product to my friends throughout the industry,” said JR.

Commenting on this appointment, Sean Allen, SVP Sales and Marketing, said, “We are pleased to welcome a proven change agent in life underwriting to our growing team. As DigitalOwl looks to drive exponential growth within the life underwriting market, we are excited to tap into JR’s expertise to help transfer tangible value to our clients in the life insurance industry, an industry that is ripe for transformation.”

Currently, JR is a member of Association of Home Office Underwriters (AHOU) and on the planning committee for the Society of Actuaries’ (SOA) Underwriting Issues and Innovation Seminar.

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