Cliff Cowles

PLANADVISER: Tell us about your role at your firm and how you contribute to its growth and progress. How did you end up there?

Cowles: I began my career as a call center representative at Charles Schwab, where I developed a strong foundation in client service and financial operations. I later joined Oswald Financial as a senior client service associate, then transitioned to client manager, deepening my involvement in retirement plan services. Today, I serve as an investment and retirement plan specialist, where I lead our plan benchmarking efforts and conduct investment analysis as a member of our investment committee. My role directly supports the firm’s growth by helping clients strive to optimize their retirement plans through strategic investment oversight and fiduciary support. This progression has allowed me to blend hands-on experience with a strategic lens to drive results.

PLANADVISER: What steps do you think will help improve the retirement industry and participant outcomes in the future (particularly ways in which your firm can help with that progress)?

Cowles: Improving the retirement industry starts with simplifying plan design and enhancing participant engagement. One key step is leveraging data to personalize communication and guidance—helping participants understand their goals and take action. At Oswald Financial, we’re focused on using benchmarking insights to drive smarter plan design and provide fiduciary-focused investment oversight. By helping plan sponsors reduce fees, improve fund menus and implement automatic features like auto-enrollment and auto-escalation, we can drive better outcomes. Additionally, ongoing education—delivered in clear, relatable terms—empowers participants to make informed decisions. As an investment and retirement plan specialist, I believe our role is to bridge the gap between data and decisions, turning insight into impact.

PLANADVISER: How do you define success in your role?

Cowles: I define success in my role as consistently meeting or exceeding performance expectations while actively contributing to both team and company goals. It’s about being a dependable team player. Success also means embracing continuous learning and growth—seeking out opportunities to expand my skills and take on new challenges that push me both personally and professionally. Whether it’s improving plan outcomes, supporting colleagues or enhancing client experiences, I measure success by the impact I make and the progress we achieve together.

Securities offered through LPL Financial, member FINRA/SIPC. Investment advisory services offered through Global Retirement Partners, DBA Oswald Financial, an SEC registered investment advisor and separate entity from LPL Financial