Jolie Fleming

Head of Digital at E*Trade Financial

As the Head of Digital at E*TRADE, Ms. Fleming leads the transformation of digital products, user experience, and design functions for E*TRADE’s retail platforms.

Ms. Fleming has a proven track record in driving transformative results for both startups and well-established corporate cultures. Prior to her current role, Ms. Fleming was a leader in start-ups and helped launch, turnaround and/or exit four Chicago technology businesses. She was an executive at OptionsHouse, a brokerage firm acquired by E*TRADE in 2016, founding member of the management team at PowerReviews, and an executive at Q Interactive, a direct marketing company. Earlier in her career, Ms. Fleming was a management consultant at CSC Index where she focused on market strategy, process redesign, and change management initiatives for Fortune 500 companies.

Ms. Fleming earned a bachelor’s degree from Northwestern University.


  • Head of Digital

    Current role

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