Jennifer Chao in

Jennifer Chao

Inspirer · DISC type id
Head of Engineering at Retool
📍 San Francisco, California, United States

Jennifer Chao is the Head of Engineering at Retool, leveraging her expertise from Stanford University to scale the engineering team. She previously helped grow Redfin from a Series C startup to a $2B public company, demonstrating significant experience in organizational growth.

Colleagues consistently describe her as a deeply kind, empathetic, and strategic leader. She is praised for her ability to solve hard problems, mentor team members, and for being a forward-thinking, low-BS manager who takes great care of her people.

During the 2008 financial crisis, she built Redfins core monetization engine, an instrumental achievement that helped the company survive the economic downturn.

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Experience
15 Years
Current Role
Head of Engineering
Job Level
Mid-senior
Location
San Francisco, California, United States
Personality Overview

How Jennifer shows up

Achievment Oriented
Confident & Optimistic
Generous

They don’t mind taking a stand if they believe in something. They usually prefer to drive the conversation. They measure a product on its merit but can be influenced by strong testimonials.

Priorities

Topics Jennifer cares about

Enterprise AI Solutions
She recently led the launch of Retool Agents, focusing on making AI practical for businesses and delivering measurable outcomes beyond just the technology itself.
Scaling Engineering Teams
She has a track record of growing engineering organizations, from helping take Redfin public to her current role leading the team at Retool.
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Career

Work history

6-2024
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

No media yetWe could not find public media appearances for this person.
Education
9-1998 - 6-2002
B.S.
Stanford University
Social presence
in
Behavioral profile

DISC profile (public)

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Influence (I)

Influence (I) reflects the degree to which a person prefers to work by influencing or persuading others. Those scoring high tend to be people oriented, motivated by social recognition and building relationships.

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