Keith Chapman

Questioner
DISC Type : c

Chief Legal Officer at Instawork

San Francisco Bay Area, United States

Overview

Keith Chapman is the Chief Legal Officer at Instawork, where he leads the legal function for the flexible staffing platform. A graduate of Rutgers Law School, his expertise is rooted in the gig economy from his time at both Instawork and Postmates. His leadership contributed to his team being named "Legal Team of the Year".

Outside of his direct legal responsibilities, Keith is passionate about building and mentoring strong teams. He publicly celebrates his colleagues achievements and fosters a growth-oriented, collaborative environment, emphasizing the importance of mentorship for sales and legal professionals alike.

His legal department at Instawork was honored as the "Legal Team of the Year" by the San Francisco Bar Association.

Personality Overview

Cautious & Analytical

Value Seeker

Systematic

They prefer to analyze every situation thoroughly.
  While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters. They are more likely than others to negotiate on pricing and terms.

Topics They Care About

Future of Work
Actively promotes Instawork's mission to connect reliable hourly workers with businesses, aiming to revolutionize the industry and drive economic opportunity.
Building Legal Teams
Focuses on hiring and developing top legal talent, leading his team to be recognized as the "Legal Team of the Year".
AI in Legal
Seeks to hire an "AI-first" commercial attorney, signaling a strategic focus on integrating artificial intelligence into his legal and transactional workflows.

Media Appearances

Keith has no verified media appearances

Work History

6-2025
Chief Legal Officer at Instawork
1-2021
General Counsel at Instawork
12-2018 - 12-2020
Associate General Counsel at Postmates Inc.
1-2018 - 12-2018
Senior Counsel at Postmates Inc.
12-2016 - 1-2018
Counsel at Postmates Inc.

Education

1997 - 2001
A.B. from Davidson College
2002 - 2005
J.D. from Rutgers Law School

More Information

Social Presence :

Prographics :

Exp : 18 Location : San Francisco Bay Area, United States Job Level : Leadership Designation : Chief Legal Officer at Instawork
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Insights For Selling To Keith

During A Call Or A Meeting

DO's

  • Keep some extra margin in hand as they will likely negotiate the pricing
  • Back up any claims with data and numbers
  • Tell them that you will come back if you don’t have a good answer for a question

DONT's

  • Don’t overhype the product/pitch, keep it measured
  • Don’t depend too much on anecdotal evidence, it reduces their confidence
  • Avoid rushing them, be polite and patient

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Keith is

  • Confidence that the product provides ROI, effective pricing and process adherence matter the most to them.

  • Will you ever get a clear answer from Keith

  • It doesn’t come naturally to them but they can say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Keith move?

  • They can move at a reasonable pace while making their decisions if they have the necessary information.

  • Can Keith take some risk or not?

  • They can take risk if they are convinced that they have analyzed the circumstances well.


You And Keith

Personality Compatibility


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