James Olson

Leafhouse
Executive Vice-President

James Olson has 25 years’ experience in the retirement plan industry. During that time, he has become an acknowledged leader in his field as the designer of forward-thinking product and service models that have had a significant impact on the retirement plan marketplace.

James got his start in the retirement industry in 1990 as a Client Services Manager for Bank of America Retirement Services while also earning Series 7 and 65 licenses. James’ career also includes working for Charles Schwab & Company as Senior Product Manager, as well Decimal Inc. (now Ubiquity) as Senior Vice President of Strategic Initiatives.

In 2002 Olson became one of the founding partners of ASPire Financial Services. During his tenure Olson helped grow the company from a start-up with 1 employee to 165 employees with $30 million in revenue, making ASPire #18 among the Tampa Bay Business Journal’s 2010 Fast 50 (honoring the 50 fastest-growing privately held companies in Tampa Bay) and making ASPire a 2010 Florida Finalist for Ernst & Young’s prestigious Entrepreneur of the Year award. As a co-founder and Chief Marketing Officer at ASPire, Olson developed and executed product strategies that have made ASPire a recognized institutional brand in the financial services market, with more than $6 billion of recordkeeping assets under administration, approximately 175,000 participants and 5,700 retirement plans.

With a strategic vision to influence the retirement markets again, Olson joined the Bluff Point Associates team in October 2013 to develop the Investment Provider Xchange (IPX) platform – —an open-investment trading platform that allows access to brand-name mutual funds, annuities, ETFs and professionally managed portfolios.

In 2024, Olson joined industry leader Leafhouse as the Executive Vice President of Product, where he is responsible for driving product design and technological advancements