CEO & COO  ·  Fintech, Consumer Investing, Data & AI

Mike Massey
builds and scales
fintech businesses.

CEO, COO, and general manager with more than 20 years building, scaling, and leading consumer financial technology businesses — with range across product, technology, data, finance, growth, operations, and regulation.

Get in touch LinkedIn Resume
Mike Massey
20+
Years in
consumer fintech
~$300M
TradeKing sale
to Ally Financial
~$8M
Debt eliminated
at UNest
+80%
AUM growth
at UNest
6
FINRA
licenses
About

An unusually complete view of how the pieces of a business connect.

Mike is a CEO, COO, and general manager with more than 20 years of experience building, scaling, and leading financial technology businesses, primarily across consumer investing and retail brokerage. His background spans product, technology, data, finance, growth, operations, and regulation — giving him a clear view of how decisions in one area affect the rest.

Most recently, he served as Chief Executive Officer of UNest, a venture-backed investment platform operating an SEC-registered RIA and FINRA-regulated broker-dealer, after being promoted from COO within three months. Earlier, he joined TradeKing as employee #12 and grew into a member of its five-person senior leadership team, helping scale the business through its approximately $300 million sale to Ally Financial.

Mike is known as a calm, principled leader who brings structure to complex situations, gets quickly to the heart of a problem, and translates strategy into disciplined execution.

Highlights

Turnaround, scale, and the products and data underneath them.

UNest · CEO

Took a regulated investing platform from heavy burn to break-even.

Held end-to-end responsibility for strategy, P&L, product, technology, operations, finance, compliance, fundraising, and Board relations across an SEC-registered RIA and FINRA-regulated broker-dealer. Rebuilt the technology and operating model, introduced AI-driven automation, and closed inherited SEC and FINRA investigations with no enforcement recommendations.

  • ~$8M debt eliminated
  • Burn ~$800K/mo → break-even
  • AUM +80%
  • 95%+ customer retention
TradeKing · Senior Executive Team

Employee #12 to the five-person leadership team — through the sale.

Helped scale the online retail brokerage to approximately 250,000 customers, 280 employees, and $75 million in annual revenue. Played a central role across company strategy, acquisitions, Board engagement, and the approximately $300 million sale to Ally Financial, which generated an approximately 10x return for its lead investor.

  • ~250K customers
  • $75M annual revenue
  • ~10x investor return
TradeKing · Product & Experimentation

Early digital investing products and a culture of testing.

Built and led product, data, experimentation, and optimization capabilities that helped drive TradeKing's growth and differentiate its customer experience — including an industry-first social trading network, an HTML5 streaming active-trader platform, and mobile applications. The experimentation model contributed to approximately 20% revenue growth.

  • Industry-first social trading network
  • ~20% revenue growth
Blue Lantern Health · Ally Financial

Deep technical and analytical fluency behind the general management.

At Blue Lantern Health, built a 21-person data organization that generated approximately $14 million in incremental revenue impact, including a 29% increase in lead conversion and a 19% improvement in marketing conversion. At Ally Financial, led a 32-person analytics and data science organization supporting banking, investing, and lending.

  • ~$14M revenue impact
  • 32-person analytics org
Range

Connecting decisions across the business.

01

Strategy & P&L

End-to-end ownership of strategy, operating plans, and profitability as CEO and COO.

02

Regulated Entities

Leadership of an SEC-registered RIA and FINRA-regulated broker-dealer, including regulator relationships.

03

Product & Technology

Digital investing products from social trading to active-trader and mobile platforms.

04

Data, Analytics & AI

Built data and data science organizations; introduced AI-driven automation into operations.

05

Finance & Fundraising

Debt reduction, burn management, and capital raising for venture-backed businesses.

06

Board, M&A & Integration

Board engagement, acquisitions, and integrating TradeKing into Ally after the sale.

Advisory & Interim Leadership

CEO- and COO-level help for broker-dealers, RIAs, and consumer investing companies.

Mike works with a select number of companies on an interim or advisory basis — bringing the same general-management range to a defined mandate, for a defined period.

Interim & registered leadership

Interim CEO, COO, or registered principal for FINRA broker-dealers and SEC-registered RIAs — through a search, a transition, or a launch.

Launch & build-out

Standing up a regulated investing business: custodian and clearing selection, account operations, RIA governance, compliance coordination, and the KPIs to run it.

Operating reset

Aligning burn, technology, and the operating model with the plan — including AI-driven automation of manual operations.

Regulatory readiness

Preparing for exams and working through regulator inquiries, informed by closing inherited SEC and FINRA investigations with no enforcement recommendations.

Discuss an engagement Project, monthly, or interim structures.
Experience

Two decades in consumer investing and retail brokerage.

  1. 2026 – Present
    Independent Advisor
    Interim Executive Leadership & Advisory
    Interim and advisory engagements with broker-dealers, RIAs, and consumer investing companies.
  2. 2024 – 2026
    UNest
    Chief Executive Officer · Chief Operating Officer (2024)
    Venture-backed investment platform operating an SEC-registered RIA and FINRA-regulated broker-dealer.
  3. 2021 – 2024
    Blue Lantern Health
    Vice President, Data
  4. 2018 – 2021
    Ally Financial
    Senior Director, Consumer Analytics
  5. 2017 – 2018
    MarketBets
    President and Chief Operating Officer
    An early prediction-market platform.
  6. 2006 – 2016
    TradeKing acquired by Ally Financial
    Online retail brokerage.
    Chief of Staff and Vice President, Data and Analytics (2011–2016)
    Director, Product Development (2006–2011)
  7. 2003 – 2006
    Capital One
    Analyst, Marketing and Analysis
    Financial models and analytical strategies supporting approximately $1 billion in identified lending opportunities. Began his career in online retail brokerage at SureTrade.com.
FINRA Licenses
Series 3 Series 4 Series 7 Series 24 Series 65 Series 66
Education

University of Georgia
Bachelor of Arts, Economics

Contact

Let's talk.

Whether you're a board, an investor, a search partner, or an operator building something in consumer investing, I'd love to hear from you — about an executive role or an interim or advisory engagement.

Send a note here and it comes straight to me.

Or connect on LinkedIn

Your details are used only to reply to you.