Meet the RetyrOne Team | Retirement Planning Professionals

Our Team

Experience, Insight and Long-Term Perspective

A team built to navigate complexity, protect outcomes and support confident decision-making.

RetyrOne was built around a simple belief:

Retirement decisions require experience, perspective, and judgment developed over time.

Our team brings decades of leadership and real-world experience focused specifically on the retirement years; particularly the transition from accumulation to distribution, where decisions behave differently and consequences compound.

This page is not about sales roles or titles.

It’s about stewardship.

A Shared Philosophy

While backgrounds and roles differ, the team at RetyrOne is aligned around a common philosophy:

Retirement decisions must be viewed as a connected system
Distribution requires a different mindset than accumulation
Clarity should come before action
Guidance should evolve as life changes

This philosophy shapes every conversation and every relationship.

Richard R. Dwyer, Jr

President

Rick began his career in the financial services industry in Fort Lauderdale, Florida, in 1987 after serving ten years in the United States Navy Submarine Service. Over the years, he has held multiple industry registrations, including General Securities Representative, General Securities Principal, Options Principal, and Investment Advisor Representative.

Following the financial crisis of 2008–2010, Rick shifted his focus exclusively to working with retirees and pre-retirees. During that period, he recognized a critical but often overlooked reality: the transition from accumulation to distribution is immediate and significant, and strategies that work well while building wealth can quietly undermine a retirement plan once income replaces paychecks.

Since then, Rick has dedicated his practice to helping people understand how retirement decisions interact over time. His work focuses on addressing the interconnected risks that emerge in retirement, including income sustainability, taxes, market risk, inflation, and legacy considerations, before timing limits available choices. His approach emphasizes structure, coordination, and clarity so individuals and families can make informed decisions with confidence.

Rick has been married to his wife, Violy, for 40 years. They have two children and two grandsons.

Annie Dwyer

Director of Technology

As Director of Technology at RetyrOne, Annie Dwyer leads the strategy, development, and integration of technology systems that power the firm’s retirement planning, client experience, and long-term growth initiatives. With more than two decades of experience spanning IT leadership, systems architecture, business development, and digital transformation, Annie brings a rare combination of technical expertise and business acumen to the organization.

Her career includes executive-level IT leadership, technology modernization initiatives, and enterprise process optimization, where she consistently transformed technology from a support function into a strategic growth engine. Annie has led large-scale infrastructure improvements, implemented disaster recovery and security frameworks, modernized legacy systems, and built scalable digital platforms that improved performance, reliability, and service delivery.

At RetyrOne, Annie focuses on building secure, intelligent, and efficient technology ecosystems that enable advisors to serve clients more effectively while delivering a seamless, trustworthy experience for families planning their financial futures. Her work directly supports operational efficiency, data integrity, automation, compliance alignment, and client-facing systems that make complex financial planning simpler, clearer, and more accessible.

Annie’s leadership philosophy centers on using technology to remove friction, improve transparency, and create confidence—both internally for the team and externally for clients. By aligning systems, data, and digital tools with RetyrOne’s mission, she ensures that technology serves as a foundation for growth, scalability, and long-term client trust.

She holds an M.S. in Data Science, a B.S. in Business Management, and an A.S. in Computer Programming and Analysis, along with multiple IT certifications, reflecting a lifelong commitment to innovation, continuous improvement, and excellence in service delivery.