The Engineering Leadership Podcast · Episode 121

Org specialization dilemmas & operating in regulatory environments

with Kenny Shin

Mar 14, 2023
Kenny Shin, CTO @ Fundrise, joins us to discuss Fundrise’s journey, specialization dilemmas as an early-stage org, why specializing eng functions can help overcome plateaus in the business, plus other insights on operating in highly regulated environments like FinTech. He also reveals another dimension of the product design process – legal / regulators – and shares how regulatory environments impact the eng team’s developmental process. Plus Kenny dishes on Fundrise’s Innovation Fund, its impact on the engineering org, and how they’re re-applying tech in new sectors.
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Kenneth J. Shin (@kennyshin7) is Chief Technical Officer of Fundrise, America’s largest direct-to-investor alternatives investment manager. He has served in this role since the company’s inception in March 2012.

Fundrise’s mission is to use technology to build a better financial system for the individual investor, one that is simpler, lower cost, more reliable and transparent. They build software that enables the company to develop and manage investments uniquely well-positioned to grow and preserve their clients’ capital in any economic environment.

Since launching America’s first online real estate investment platform in 2012, Fundrise has now become the largest direct-to-investor alternatives investment manager with more than 1.6 million active users, more than $3.3 billion worth of equity under management, and $7 billion worth of real estate transacted. From private credit to real estate private equity to growth-stage venture capital, Fundrise offers investors exposure to some of the most prized asset classes in the world.

Prior to Fundrise, Kenny has consulted for Fortune 500 clients in financial services and technology, including Fannie Mae, Oracle, Lockheed Martin and Computer Science Corporation. Kenny has also consulted for government clients including the Federal Bureau of Investigation, Department of Defense and NATO. Kenny earned his Bachelor of Science in Computer Science Engineering from the University of Pennsylvania.

"The entire industry generally has to try to abstract all of that complexity and regulation away from the end user and the companies that do that the best, that's one of their main value propositions.

I think it's key to our operations because the opposite of it is you leave that complexity to a few subject matter experts in the organization and they become the bottleneck for everything.”

- Kenny Shin   

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  • Kenny’s journey co-founding Fundrise (2:37)
  • What Kenny’s early risk assessment looked like (4:58)
  • Advice for young eng talent considering taking a riskier role (8:12)
  • Fundrise’s evolution & key inflection points (9:45)
  • How Fundrise tackled uncertainty during the pandemic’s early days (11:52)
  • Addressing specialization dilemmas as an early-stage org (14:45)
  • Why specializing eng functions helped Fundrise overcome its plateau (16:08)
  • Kenny’s approach to identifying new opportunities around specialization (19:53)
  • Challenges of operating in a constrained space, like Fintech (23:38)
  • Why constrained industries require orgs to abstract away more complexities (25:03)
  • How regulatory environments impact the eng team’s developmental process (26:46)
  • Incorporating legal / regulators into your product design process (29:17)
  • The Innovation Fund & its role within Fundrise’s overall strategy (31:52)
  • Unexpected ways the Innovation Fund is impacting the engineering function (34:04)
  • Rapid fire questions (36:47)


  • Crying in H Mart - In this exquisite story of family, food, grief, and endurance, Michelle Zauner proves herself far more than a dazzling singer, songwriter, and guitarist. With humor and heart, she tells of growing up one of the few Asian American kids at her school in Eugene, Oregon; of struggling with her mother’s particular, high expectations of her; of a painful adolescence; of treasured months spent in her grandmother’s tiny apartment in Seoul, where she and her mother would bond, late at night, over heaping plates of food.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer -

Ellie Coggins Angus - Copywriter, Check out her other work at

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