Doug Twiddy

Doug brings over 15 years of hands-on experience in annuity strategy, retirement planning, and advisor support to his role at Matador Insurance Services. As a trusted strategist to financial planners and wealth advisors, Doug has built a reputation for designing tailored, layered retirement income plans that help clients get the most out of every dollar in retirement.

At Matador, Doug plays a key role in helping clients navigate the complex intersections of annuities, Social Security, pensions, taxes, and long-term care risk. His strategic planning sessions are more than just product selection—they’re personalized, data-backed roadmaps for creating reliable, tax-efficient income streams that align with each client’s unique retirement goals.

Doug’s custom-built Pension Maximization Analyzer, an 18-page comprehensive income report, has helped dozens of advisors simplify decisions around pension options, Social Security timing, and income distribution. His ability to pull all the moving pieces together into a clear and actionable plan makes him an invaluable resource to Matador’s planning team and clients alike.

While he doesn’t consider himself a salesperson, Doug thrives in client conversations. His presence on advisor-client calls brings clarity, product insight, and confidence—allowing the advisor to focus on guiding the relationship while Doug supports the technical side of the recommendation.

In addition to his role at Matador, Doug is deeply committed to professional growth and is currently furthering his studies at The American College of Financial Services. He’s also passionate about educating the public and has traveled extensively across Virginia hosting Social Security workshops for advisors and clients.

Outside of work, Doug is a dedicated family man. He and his wife Ashley are raising four wonderful children—Kaylee, Lilli, Damian, and Lucas. He’s an Eagle Scout and former Scoutmaster, a longtime youth sports coach, and a swim team leader in his community. Whether it’s in the field, at the pool, or out on a hiking trail, Doug is always finding ways to lead, serve, and stay active.