Deirdre Ragan, Chief Operating Officer at Healthcare.com

Deirdre Ragan

Chief Operating Officer at Healthcare.com | Santa Fe, New Mexico, United States

Profile last verified June 2026
Insurance Verified Profile Santa Fe, New Mexico, United States The University of Texas at Austin
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***@dkrbc.com

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(505) ***-*517

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Deirdre Ragan Socials
Deirdre Ragan Work Experience

President at Pivot Health in October 2022 - Present

Chief Operating Officer at Healthcare.com in January 2025 - Present

Senior Vice President, Insurance at Healthcare.com in October 2022 - January 2025

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Vice President, Insurance and Coverage Solutions at Healthcare.com in June 2021 - October 2022

President and Founder at DKR Business Consulting LLC in January 2019 - June 2021

Vice President and Director, Technology & Program Management at National Guardian Life Insurance Company in January 2016 - January 2019

Vice President, New Initiatives at National Guardian Life Insurance Company in January 2015 - January 2016

Executive Vice President, Strategy and Business Development at Madison National Life Insurance Company in January 2012 - January 2015

Senior Vice President at Madison National Life Insurance Company in January 2004 - January 2012

Vice President at Madison National Life Insurance Company in January 1996 - January 2004

Vice President and Principal at Hill Country Acquisition Consultants in January 1994 - January 1996

Assistant Vice President at Columbia Universal Life Insurance Company in January 1989 - January 1994

Deirdre Ragan Education

The University of Texas at Austin, Bachelor of Science (BS)

Deirdre Ragan Skills
Acquisitions Insurance Reinsurance Strategic Planning Enterprise Risk Management Product Development Product Management Agile Methodologies Team Building Health Insurance Scrum Life Insurance Due Diligence Process Improvement Risk Management Kanban Mergers & Acquisitions Executive Management Strategy Business Development Business Analysis Underwriting Fixed Annuities Employee Benefits Actuarial Science Claims Management Management Business Process Improvement
About Deirdre Ragan’s Current Company
Healthcare.com

Founded by industry experts in 2014, Healthcare.com is a data-driven, intelligence-informed marketplace where millions of consumers have explored, shopped for and enrolled in health insurance and Medicare plans. We put care, data, and a decade of experience into helping you choose the right plan. With us you can easily shop health plans for individuals, for families, for seniors. Trusted by 10 million customers a year, Healthcare.com is the data-driven choice that matches you to the right health insurance plan. We use proprietary data and machine learning technology to match consumers with distributors, ensuring each consumer gets enrolled in the right plan for them and their families. Healthcare.com also operates Pivot Health, an insurance marketing company and healthcare services provider that offers a variety of coverage options to consumers on behalf of top-ranked insurance carriers and healthcare organizations. We develop custom health insurance programs and coverage solutions in partnership with insurance carriers. In addition to our own solutions, we have put together a portfolio of non-proprietary health insurance and healthcare solutions that we believe meet the needs of our individual members. Our products range from short-term medical insurance, dental and vision, supplemental indemnity, and accident and illness products.

Discover more about Healthcare.com
Deirdre Ragan’s Colleagues
David B

David B

Denver, Colorado, United States

Digital Marketing Lead | Says Please & Thank You to AI

Digital Marketing Lead at Healthcare.com
(Dec 2023 – Present)

Dennis Li

Dennis Li

West Hartford, Connecticut, United States

Insurance Strategist | Speaker | Bridging Gaps Across the Insurance Value Chain

VP of Strategic Partnerships at Healthcare.com
(Aug 2025 – Present)

Marianne Liberatore

Marianne Liberatore

New York, New York, United States

InsurTech Executive Leader | Enterprise Revenue Growth

• Direct the global B2B sales, account management, and client success strategies for a leading healthcare technology company providing lead generation marketing, call and warm transfer prequalification services, pay-per-click (PPC) marketing, brand promotion, and data scienc...

Dana L

Dana L

Beverly Hills, California, United States

Data Science Management / Machine Learning / Data Engineering / Generative AI

Focused on data science for website optimization, machine learning for marketing insurance products to consumers, AI for voice technolgy

Anju Pandey

Anju Pandey

United States

Sr. Talent Acquisition Specialist - MBA

Accomplishments:
● Joined at the peak of hiring with a large number of openings and enormous backlog. Hit the ground running with minimal supervision and handholding.
● Was able to pull together the first offer for a Sr Data Scientist role within 10 days of joining.
● Wo...

Austin Larrowe

Austin Larrowe

Daleville, Virginia, United States

VP, Strategic Execution & Biz Ops @ Healthcare.com | Strategy → Execution at Scale

Promoted to convert Healthcare.com’s boldest growth bets into scalable, repeatable wins - bridging strategy and execution so every high-conviction idea ships faster, scales bigger, and compounds value for the business and its partners.

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Frequently asked questions about Deirdre Ragan

What is Deirdre Ragan email address?

Email Deirdre Ragan at [email protected] and [email protected]. This email is the most updated Deirdre Ragan's email found in 2026.

How to contact Deirdre Ragan?

To contact Deirdre Ragan send an email to [email protected] or [email protected].

What company does Deirdre Ragan work for?

Deirdre Ragan works for Healthcare.com.

What is Deirdre Ragan's role at Healthcare.com?

Deirdre Ragan is Chief Operating Officer

What industry does Deirdre Ragan work in?

Deirdre Ragan works in the Insurance industry.

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