Jennifer Chao

Inspirer
DISC Type : id

Head of Engineering at Retool

San Francisco, California, United States

Overview

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.

Personality Overview

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.

Topics They Care 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.
Developer Productivity
Her work at Retool is centered on creating platforms that allow developers to build internal applications and software more efficiently.

Media Appearances

Jennifer has no verified media appearances

Work History

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

Education

9-1998 - 6-2002
B.S. from Stanford University

More Information

Social Presence :

Prographics :

Exp : 15 Location : San Francisco, California, United States Job Level : Mid-senior Designation : Head of Engineering at Retool
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Insights For Selling To Jennifer

During A Call Or A Meeting

DO's

  • Refer to testimonials from well known people to highlight the value of your product
  • Get them to a point where they are ready to bat for your product internally
  • Acknowledge their status and position during the conversation

DONT's

  • Don't be unorganized, be prepared for the pitch
  • Don’t be too verbose or overly friendly; a little bit, however, is fine
  • Avoid focusing only on the product or its ROI, keep building trust subtly

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jennifer is

  • Belief in the value of the product, relationship and a sense of accomplishment matter the most.
  • Will you ever get a clear answer from Jennifer

  • They are not shy of saying no if they do not develop trust in your product.

Insights For Deal Planning

    How fast (or slow) will Jennifer move?

  • They can take fast decisions if they develop conviction in the product and find you trustworthy.
  • Can Jennifer take some risk or not?

  • They have the capability of taking risky decisions if necessary.

You And Jennifer

Personality Compatibility


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