Michael Eskenasy

Commander
DISC Type : D

Founder & Architect — ChefreyOS | Human Cognitive Infrastructure at ChefreyOS

Spokane-Coeur d'Alene Area, United States

Overview

Michael Eskenasy is the Founder and Architect of ChefreyOS, a system designed to reduce cognitive overhead in work. His background includes technical program management at major tech companies like Amazon, Twilio, and Truepill, along with an MBA from California Lutheran University.

He has a philosophical approach to work and business, writing about topics like burnout, decision integrity, and building companies with a purpose beyond exponential growth. His interests extend to analyzing the operational continuity of unique businesses, from historic properties to wineries.

Unique fact: He has publicly stated he cannot raise traditional venture capital because his business model is not built around the promise of selling the company.

Personality Overview

Impact-Driven

Very Quick

Candid & Clear

More than the product, they care about the effectiveness of the product.  They are not focused on building rapport and relationships. They respond well to strong and respectful communication.

Topics They Care About

Cognitive Overhead
He is building ChefreyOS specifically to eliminate cognitive overhead, preserving intent, context, and relationships to make work feel lighter and clearer.
System Coordination
He posits that coordination, not task execution, is the real unit of work and focuses on building systems that manage handoffs and context between people and tools.
Decision Integrity
He wrote a publication on "decision drift," exploring how good teams lose coherence when decisions become detached from their original intent and constraints.

Media Appearances

Michael has no verified media appearances

Work History

1-2026
Founder & Architect — ChefreyOS | Human Cognitive Infrastructure at ChefreyOS
9-2022 - 6-2025
Founder at DragonflySM
4-2022 - 9-2022
Principal Technical Program Manager at Truepill
2-2019 - 4-2022
Technical Program Manager / Senior Technical Project Manager at Twilio
7-2018 - 2-2019
Sr. Technical Product Manager, Performance Engineering at Amazon

Education

1-2009 - 12-2010
Master of Business Administration from California Lutheran University
1-2007 - 12-2009
Bachelor of Science from California Lutheran University

More Information

Social Presence :

Prographics :

Exp : 7 Location : Spokane-Coeur d'Alene Area, United States Job Level : Leadership Designation : Founder & Architect — ChefreyOS | Human Cognitive Infrastructure at ChefreyOS
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Insights For Selling To Michael

During A Call Or A Meeting

DO's

  • Make sure that you circle back fast on any action items, it wins their trust
  • Hold your ground without indulging in one-upmanship
  • When negotiating terms, help them build an impression that they are the ones calling the shots

DONT's

  • Don’t take too much time in sending them information if they ask for any
  • Don’t be in a rush to invite them for a social meet and greet
  • Don't try too hard to forge relationships with them

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Michael is

  • Confidence in impact is paramount to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Michael

  • If they decide not to go ahead, they will say no without hesitation.

Insights For Deal Planning

    How fast (or slow) will Michael move?

  • They can take decisions very fast if you manage to convince them.
  • Can Michael take some risk or not?

  • The risks don’t matter much to them.

You And Michael

Personality Compatibility


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