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Willie Jackson

Writer and facilitator. I help teams and organizations change how they work together, and lately how they work with AI agents too.

Willie Jackson

Over the years, I’ve…

WhenWhatEssay
5th gradeSold mistletoe door to door in the fifth grade (and learned what happens when you run out of product)Read
2010Deployed enterprise software across the country for Accenture, then walked away from the cubicle in 2010 with no planIdea
[YEAR]Was CTO of The Domino Project, Seth’s publishing experiment powered by AmazonIdea
2015Built the tech behind Seth Godin’s altMBA, now 7,000+ alumni in 100+ countriesIdea
2015Ran a magazine for Black men out of Harlem and published 400+ stories in four yearsIdea
c. 2015Sat across from a new client who started telling racial jokes at our kickoff meetingRead
2017Gave a talk in Berkeley, got recruited as hire #3 at ReadySet, and stayed six yearsRead
2017–24Led ReadySet trainings from Portland to Portugal for 200+ organizationsIdea
[YEAR]Went house hunting on HGTVIdea
2026Started managing AI agents like direct reports (and taught one to run the servers in my closet)Read

What I write about

TopicPublishedNext up
Holding the room A teacher’s turning point
Feedback for you and for me
Act like you want to be there
How I open a room in the first five minutes
Managing humans and agents Agentic Management
Trust and ego in management
Unnecessary heroics
AI upskilling is a management problem, not a training problem
The Seth Godin years None yet Building the altMBA: learning infrastructure for 7,000 people
Media and identity A love letter to Oak Bluffs
The Fierce Urgency of Compassion
Four years of publishing a magazine for Black men
Culture work Six & Change
From Day One
A message for the moment
What inclusion work actually changed
The portfolio career Accruing Assets
What’s in a Power Circle?
The problem with waiting
From IT consultant to facilitator
Tinkering The vibes are right I let an AI run the servers in my closet
People and places Strengthening weak ties
Mutual introductions
You just had to be there
Jacksonville made me

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