Building a Tech-Forward Financial Planning Platform with Pat O’Boyle, USNA ‘14

Pat O'Boyle is the Chief Compliance Officer at Gleneagle Advisors and a member of the leadership team behind Alooola, a technology-driven financial planning and investment platform. In addition to overseeing regulatory compliance, he supports business development and helps drive the growth of Aloooa's advisory and retirement planning services, including its expanding 401(k) platform for business owners. A graduate of the U.S. Naval Academy, Pat served as a Marine Corps infantry officer with 7th Marines and completed two deployments to the Middle East. After transitioning from military service, he built experience across investment banking, fintech, and wealth management through roles at Wells Fargo Securities, EquitiesEnd, and CBIZ before joining Gleneagle Advisors to help scale Alooola's technology-first approach to financial planning. In this episode of the SABM podcast, Scott chats with Pat about: From the Marine Corps to Financial Services: How military leadership, investment banking, and startup experience ultimately led to helping build a technology driven planning platform. Creating Alooola’s Hybrid Approach: Combining personalized financial advice with a mobile-first experience that keeps advisors accessible to clients. Helping Businesses Reduce 401(k) Costs: Helping business owners uncover hidden retirement plan fees while improving retirement plan offerings. How Technology Enhances the Advisor Relationship: Using technology to simplify investment management and create more meaningful client conversations. Building the Future of Financial Planning: Bringing investing, retirement planning, tax strategy, insurance, and advisor support into one platform. Timestamps: 01:13 Marine Corps to Finance 02:10 Wells Fargo and COVID Markets 04:27 Startup Culture Shift 05:51 Joining Gleneagle and Alooola 09:06 Alooola App Overview 12:40 Why Build the App 14:57 Advisors Using the Platform 18:19 Building with AI and Compliance 21:49 Goals for 2026 and Beyond 25:08 Who They Help Most If you found value in today's episode, don't keep it to yourself—share it with a colleague or friend who could benefit. And if you're a Service Academy graduate ready to elevate your business, we'd love for you to join our community and get started today. Make sure you never miss an episode. Subscribe now and help support the show: -Apple Podcasts -Spotify Leave us a 5-star review! A special thank you to Ryan for joining me this week. Until next time! -Scott Mackes, USNA '0