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Isaac Chiles
Isaac Chiles

Isaac Chiles has been on both sides of the enterprise sales table — first as a customer, now as a Sales Executive — and he’s learned a lot along the way about what works and what doesn't when it comes to driving business transformation. With nearly a decade in AI-powered workflows, solution consulting, and sales, Isaac’s career has been about finding the sweet spot between technology and real-world business impact. He’s grown territories from 10x, created workshops, been a featured speaker, and built demos that actually help people understand how solutions work in the real world. And he founded eduSwipe, a digital publishing platform that brought authors onto a new business model, shaking up the traditional publishing industry. Isaac believes that anything we spend much of our lives doing is worth doing well, and that learning is always a two-way street. While he’s happy to share what he’s learned from his journey in solution consulting and sales, he’s just as eager to learn from others. Sharing ideas isn’t about lecturing—it’s about creating conversations where everyone can grow, improve, and get better at what they do, together.

Questions From the CIO: Nothing to Declare

Sep 14, 2026

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2 min read

Questions From the CIO: Nothing to Declare

Sanctioned, well-intentioned, and invisible to every instrument you own.

Isaac Chiles
Isaac Chiles
Questions From the CFO - What the Tokens Bought

Sep 1, 2026

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3 min read

Questions From the CFO - What the Tokens Bought

What AI spend looks like from the CFO's chair: two numbers for what it costs, neither of which says what it bought, and where the return actually becomes visible. First in the series for the CFO seat.

Isaac Chiles
Isaac Chiles
The Boring Miracles

Aug 27, 2026

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8 min read

The Boring Miracles

The future is amazing: Weather forecasts, enzymes, and a robot in Berkeley — four things quietly deciding the next twenty years, none of which will ever trend.

Isaac Chiles
Isaac Chiles

Questions From...

Questions From the COO: You Don't Have an Agent Problem. You Have a Job Architecture Problem.

Aug 25, 2026

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4 min read

Questions From the COO: You Don't Have an Agent Problem. You Have a Job Architecture Problem.

Everyone is asking where to put the agents. The COOs I sit with are asking a harder question about what a job is.

Isaac Chiles
Isaac Chiles
The waiting problem

Aug 21, 2026

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4 min read

The waiting problem

Why the hours AI gave back never arrived in the business — and the thing about agents that might finally change it.

Isaac Chiles
Isaac Chiles
Questions from the Board: We Deployed It

Aug 18, 2026

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3 min read

Questions from the Board: We Deployed It

What your board is actually being told when management says "we've deployed AI" — and the one question that would tell you whether any of it worked. First in a series: what I'm actually hearing from the seats I sit across from.

Isaac Chiles
Isaac Chiles

Excursion

The Second Jump

Aug 13, 2026

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3 min read

The Second Jump

Same rope. Same drop. Same exact stop. Completely different jump — because the second time, I knew what was coming.

Isaac Chiles
Isaac Chiles

Field Notes

Field Notes: Bespoke front end

Aug 11, 2026

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1 min read

Field Notes: Bespoke front end

Can old rails meet the new front door?

Isaac Chiles
Isaac Chiles

The Human Side

+2

Most AI Rollouts Improve Everything Except the One Thing That Matters

Aug 5, 2026

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2 min read

Most AI Rollouts Improve Everything Except the One Thing That Matters

The tools worked. Adoption was real. The number the whole rollout was supposed to move never moved. Here's what I now know for certain about why — and the one part of it that still isn't settled.

Isaac Chiles
Isaac Chiles

AI Adoption

+2

The Permission Window

Aug 4, 2026

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3 min read

The Permission Window

Why AI governance gets decided in a configuration workshop, weeks before anyone calls it governance — and the question I still haven't answered about who should own that moment.

Isaac Chiles
Isaac Chiles

AI Adoption

+1

I Named My Newsletter The Increment. Here's the Half I Left Out.

Jul 20, 2026

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3 min read

I Named My Newsletter The Increment. Here's the Half I Left Out.

Why getting a little better only works if you're getting better at the right thing — and what that means for the AI decision sitting in front of you right now.

Isaac Chiles
Isaac Chiles

Work Smarter

+3

You can just build things

Jul 7, 2026

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4 min read

You can just build things

What a free job-search app, a $20 subscription, and a willingness to try taught me about the decade ahead — for all of us.

Isaac Chiles
Isaac Chiles

The Human Side

+1

The Model Is the Easy Part

Jun 23, 2026

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5 min read

The Model Is the Easy Part

Why I'm convinced the next decade of AI value goes to the people who can read a room, not just a model card.

Isaac Chiles
Isaac Chiles

Built with AI

+1

JobTracker — Announcement

Jun 18, 2026

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1 min read

JobTracker — Announcement

A Free Tool for the Job Search

Isaac Chiles
Isaac Chiles

Week In Review

Week 38 - In Review

Oct 15, 2024

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4 min read

Week 38 - In Review

The US government had a week to forget, breathing and chewing well, and a magnificent view of the heavens.

Isaac Chiles
Isaac Chiles

Week In Review

+1

Week 37 - In Review

Oct 4, 2024

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7 min read

Week 37 - In Review

Alternative energy, the power of movement, and a history of breathing

Isaac Chiles
Isaac Chiles

Presentations

+1

Fostering Engagement: The Power of Movement in Sales Presentations

Sep 30, 2024

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10 min read

Fostering Engagement: The Power of Movement in Sales Presentations

Unlock Dynamic Interactions and Create Space to Build Relationships Through Active Audience Participation

Isaac Chiles
Isaac Chiles

Process

+1

Build an MVP to deliver on time and on budget

Oct 4, 2022

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4 min read

Build an MVP to deliver on time and on budget

Tight timeline, small budget? Use these to your advantage and deliver great products

Isaac Chiles
Isaac Chiles

Work Smarter

Finding Time

Sep 24, 2022

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6 min read

Finding Time

Stephen Covey's Important / Urgent Matrix

Isaac Chiles
Isaac Chiles

Work Smarter

Work the right work

Sep 12, 2022

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8 min read

Work the right work

Confusing busyness with productivity

Isaac Chiles
Isaac Chiles

Process

Digitizing a process

Sep 12, 2022

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6 min read

Digitizing a process

Plan ahead to get it right

Isaac Chiles
Isaac Chiles

The Increment

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The Increment

The human side of enterprise AI adoption. The capability is real, and it gets cheaper every month. Most organizations still aren't getting value from it. The gap between those two facts is what this newsletter is about. I'm working it out in the open — three years buying enterprise software, seven years selling it, and a decade watching what platforms actually do to the people who have to use them. Every edition is what I'm currently thinking, including the parts I haven't finished thinking. Essays every other week. Field notes in between. For the people accountable for whether any of this actually lands.

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