Jennifer Chao in

Jennifer Chao

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Head of Engineering at Retool
📍 San Francisco, California, United States

Jennifer is an engineering leader, formerly the Head of Engineering at Retool, who is now advising teams and building her own AI products. A Stanford University graduate, she has a track record of scaling companies, including helping Redfin grow to a $2B IPO. People often describe her as kind, empathetic, strategic, and technically smart.

Originally from Texas, Jennifer is intentional about balancing her demanding career with her life as a wife and mother. To relieve stress, she enjoys taking days off to explore wine country or visit a spa with her husband. She values organic knowledge-sharing and focused time at work.

She helped Redfin survive both the 2008 financial crisis and the COVID-19 pandemic by building their core monetization engine and leading a pivot to virtual services.

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Experience
16 Years
Current Role
Head of Engineering
Location
San Francisco, California, United States
Personality Overview

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Communication Style
Decision Approach
Work Preference

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Priorities

Topics Jennifer cares about

Practical AI Applications
Her recent focus at Retool was launching practical AI tools for businesses, such as Retool Agents and an enterprise AppGen platform, to drive measurable outcomes.
Engineering Leadership
Having led a 130-person team, she is praised in recommendations as a kind, empathetic leader and deliberate mentor who takes great care of her people.
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Career

Work history

6-2024 - 2-2026
Head of Engineering
Retool
9-2023 - 6-2024
Chief Technology Officer
Pinwheel
11-2016 - 6-2022
Vice President, Engineering
Redfin
12-2014 - 11-2016
Director, San Francisco Engineering
Redfin
7-2014 - 12-2014
Senior Engineering Manager, Customer Engagement
Redfin
In the press

Media appearances

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Education
9-1998 - 6-2002
B.S.
Stanford University
Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

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