The Engineering Leadership Podcast · Episode 95

Leading through ‘black swan’ events & pivoting AI/ML product strategy

w/ Bridget Frey

Aug 02, 2022
We discuss the challenges with leading eng orgs through unpredictable global events (like the covid-19 pandemic) & pivoting product strategy with Bridget Frey (CTO @ Redfin). We also cover the challenges & successes of building out AI/ ML products in your engineering org, creating an “uncertainty” algorithm, incorporating mental health best practices in your teams, and addressing data bias & systemic racism in your product’s features! Featuring guest co-host Ali Littman (Interim Head of Eng @ Modern Health).
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As Redfin’s Chief Technology Officer, Bridget Frey (@SVBridget) leads the software engineering and analytics teams. Her mission is to build technology that makes the process of buying and selling a home less complicated and less stressful. She is a leader on issues facing traditionally underrepresented people in technology, and 36% of Redfin’s technology team are women while 10% are Black or Latinx. Prior to Redfin, Frey was the director of analytics and business applications at Lithium Technologies. In addition, she has held management positions at IntrinsiQ Research, IMlogic and Plumtree Software. Since 2019, she has served on the board of directors for Premera Blue Cross. Bridget holds a bachelor's degree in computer science from Harvard University, where she graduated magna cum laude. She was recently recognized as a Seattle CIO of The Year award winner.

"One of the things we built was this concept of virtual touring. So you could stay on your couch, but have an agent visit a home, but we could only get a very small number of people to hit that button. Despite all of our trying, we only had 1% of our tours happening virtually and then the pandemic hit and almost overnight, it jumped to about a third of our tours being virtual."

- Bridget Frey   

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  • How Bridget lead a real estate tech org through a pandemic & tumultuous housing market (1:05)
  • COVID-19’s impact on the healthcare tech space (2:02)
  • How to adapt product strategy based on customer patterns (5:02)
  • Leading with transparency & decisiveness in uncertain times (7:20)
  • Redfin’s transition to digitizing traditionally in-person experiences (10:58)
  • The pandemic’s unexpected influence on employee mental health & burnout (16:14)
  • How your org can implement a company-wide “no meeting” / wellness week (19:43)
  • Set your org up for faster decision making & implementation (23:52)
  • Challenges & solutions when building out AI/ML home buying products (25:06)
  • Incorporating human needs, desires & perspectives in automated recommendation products (27:40)
  • Engineering best practices for uncovering deeper customer needs (30:06)
  • The inside scoop on modeling an “uncertainty” algorithm (31:12)
  • Prioritization conversations & product strategy at Redfin (34:31)
  • Addressing data bias & systemic racism within product features (36:33)
  • How hiring diversely leads to reduced data bias (39:06)
  • A framework for reducing biased data outputs (40:20)
  • What hiring practices lead to a more diverse team (43:43)
  • How tech orgs can cultivate a culture of inclusivity & diversity (46:08)
  • Rapid fire questions (48:51)
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