Jake Gasaway

Organizer
DISC Type : Sd

Area Vice President of Sales, Northeast Emerging Market at Okta

Greater Chicago Area, United States

Overview

Jake Gasaway is the Area Vice President of Sales at Okta, focusing on the Northeast Emerging Market. His career includes enterprise sales at Google Cloud and co-founding Stitch Labs, a SaaS startup acquired by Square. He holds an MBA from Saint Marys College of California.

Outside of his professional life, Jake holds a deep respect for military veterans, inspired by his fathers service in Vietnam. He values building and leading strong teams and appreciates humor in the corporate world.

He co-founded a successful SaaS company, Stitch Labs, which was later acquired by Square.

Personality Overview

Strong-minded

Trusting Of Others

Somewhat Formal

They exhibit a rare combination of being result-oriented but patient at the same time.  They are very professional in their approach and can weigh multiple perspectives together. Reading between the lines and seeing beyond your words comes naturally to them.

Topics They Care About

AI Security
He is actively hiring to meet CISO demand for securing AI, stating the answer to securing it starts with identity.
Identity Management
His work at Okta is centered on the principle that "Identity is Everything, " promoting it as critical infrastructure for modern enterprises.
Sales Leadership
He is building out his sales team at Okta and is described in recommendations as a "natural leader" and "exceptional communicator. "

Media Appearances

Jake has no verified media appearances

Work History

2-2025
Area Vice President of Sales, Northeast Emerging Market at Okta
6-2022 - 2-2025
Sales Director at Okta
9-2016 - 6-2022
Enterprise Sales - Google Cloud at Google
9-2015 - 8-2016
Co-Founder: VP of Platform at Stitch Labs at Stitch Labs (acquired by Square)
1-2011 - 8-2015
Co-Founder, Director of Business Development at Stitch Labs (acquired by Square)

Education

1998 - 2003
Bachelor of Business Administration from Western Michigan University
2009 - 2010
MBA from Saint Mary's College of California

More Information

Social Presence :

Prographics :

Exp : 18 Location : Greater Chicago Area, United States Job Level : Senior Designation : Area Vice President of Sales, Northeast Emerging Market at Okta
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Insights For Selling To Jake

During A Call Or A Meeting

DO's

  • Stick to your standard pitch and qualifying script, don't try to wing it
  • You can spend time on BANT (or other qualification methodology) but keep it to the point
  • Focus on the results that your product produces, expect some strategic questions in return

DONT's

  • Don't focus too much on mutual contacts or bother about other stakeholders, focus on them
  • Don't go over them unless you are left with no other option
  • Don't get into pricing discussions early on, steer conversation towards proven results

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jake is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Jake

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Jake move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Jake take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Jake

Personality Compatibility


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