Cassy Olson

Pioneer
DISC Type : DIS

Developer GTM - Strategic Accounts at Cloudflare

Austin, Texas, United States

Overview

Cassy is on the Developer Go-to-Market team for strategic accounts at Cloudflare, where she has worked for over nine years. She focuses on helping engineering-led organizations scale using Workers, AI, and edge computing. People who have worked with her describe her as creative, professional, and persistent.

Based on her professional focus, she is likely passionate about the future of technology and how developers can build more efficiently. She attended the University of Wisconsin-Eau Claire, where she earned a Bachelor of Business Administration.

Unique fact: While at Cloudflare, Cassy closed the largest Zero Trust deal in the companys history in 2023.

Personality Overview

Dynamic But Sincere

Friendly But Fast

Driven But Considerate

If they are convinced, they can become very strong champions for your product  They have the unique ability to win both love and respect from their team (or outsiders) They combine a unique set of diverse traits where they are fast and friendly but can slow down to be thorough when needed

Topics They Care About

AI Agent Infrastructure
She frequently posts about the infrastructure needed to build and run reliable AI agents at scale, referencing Cloudflare's stack for orchestration, isolation, and frameworks.
Developer GTM
Her current role and recent posts focus on the go-to-market strategies for developer-centric tools, aiming to reduce friction and complexity for engineering teams.
Edge Computing
Cassy chronicles the evolution of the 'Edge' to the 'Everywhere, ' believing the future lies in ending the concept of regional infrastructure for developers.

Media Appearances

Cassy has no verified media appearances

Work History

1-2026
Developer GTM - Strategic Accounts at Cloudflare
1-2025 - 1-2026
Senior Majors Account Executive at Cloudflare
1-2020 - 12-2024
Enterprise Sales - Austin / San Antonio at Cloudflare
2-2017 - 12-2019
Mid Market Account Executive at Cloudflare
2016 - 2017
Mid-Market Account Executive at Egnyte

Education

Bachelor of Business Administration from University of Wisconsin-Eau Claire

More Information

Social Presence :

Prographics :

Exp : N/A Location : Austin, Texas, United States Job Level : N/A Designation : Developer GTM - Strategic Accounts at Cloudflare
URL has been copied!

Insights For Selling To Cassy

During A Call Or A Meeting

DO's

  • Build a trustworthy relationship while keeping the product center-stage
  • Ask them for a lunch or coffee once some rapport has been established
  • Keep your pitch focused on the impact but nurture the relationship too

DONT's

  • Don’t be too verbose or overly friendly; a little bit, however, is fine
  • Don’t be very informal during the early interactions even if they are being so themselves
  • 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 Cassy is

  • Nothing less than a strong combination of proof of results, relationship and high levels of professionalism is effective with them.
  • Will you ever get a clear answer from Cassy

  • They can say no while staying friendly, but can also be pursuaded to reconsider

Insights For Deal Planning

    How fast (or slow) will Cassy move?

  • They are generally fast movers and can take quick decisions
  • Can Cassy take some risk or not?

  • They have high risk-appetite but can get ahead of themselves once in a while. Observe carefully

You And Cassy

Personality Compatibility


Other Cloudflare Employees

Explore more public profiles from related professionals at the same organization.

More Profiles

Discover additional public profiles from our index.

Search more profiles

Looking for someone else? Search here for anyone.

Or visit Humantic AI to know more.