Michael Eskenasy in

Michael Eskenasy

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Founder & Architect — ChefreyOS | Human Cognitive Infrastructure at ChefreyOS
📍 Spokane-Coeur d'Alene Area, United States

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.

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Experience
7 Years
Current Role
Founder & Architect — ChefreyOS | Human Cognitive Infrastructure
Job Level
Leadership
Location
Spokane-Coeur d'Alene Area, United States
Personality Overview

How Michael shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Michael cares 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.
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Career

Work history

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

Media appearances

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Education
1-2009 - 12-2010
Master of Business Administration
California Lutheran University
1-2007 - 12-2009
Bachelor of Science
California Lutheran University
Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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