Live workshop · October or December 2026
AI Player-Coach OS
The hands-on AI workshop for product leaders who have to lead AI adoption, not talk about it.
October · Tue 6, Thu 8, Tue 13, Thu 15
December · Tue 1, Thu 3, Tue 8, Thu 10
9–11am PT · Live on Zoom · 4 sessions, 8 hours
Your team is looking to you to lead on AI. Your own hands-on experience is the credibility gap.
Most AI training for product people is built for individual contributors. Faster PRDs, better prompts, a personal productivity boost.
That stopped being your job description a while ago. As a Director, VP, or Head of Product, you decide how your team uses AI, set the standards, and answer the security questions from leadership. Doing that credibly from demos and articles is hard. Doing it from hands-on experience changes the conversation.
In this workshop you build a real agentic AI system on your own machine and your own work. You also understand how the system works: well enough to extend it, adapt it for your team, and keep it safe inside your company.
What you’ll build
Session 1 · Tuesday, October 6 or December 1
Claude Code becomes your personal operating system
Context and memory that carry from one session to the next, and the commands you’ll run every day.
Session 2 · Thursday, October 8 or December 3
A chief of staff agent
Connected to the apps you already use, running your week and picking up scheduled work without being asked.
Session 3 · Tuesday, October 13 or December 8
An agent that helps you manage your team
Several agents working on a single job in parallel, and the patterns for rolling the approach out to the people you lead.
Session 4 · Thursday, October 15 or December 10
Team collaboration and automation
Share your knowledge base and operating system with your team, and set up learning loops that automate the grunt work overnight, while you’re away from the keyboard.
“Totally worth the time. Particularly if you are making sure your foundation is in place and set up for success for expanding your AI practice.”
Vanessa Garber, Head of Product · September workshop
“The Player-Coach session was so good. It truly unlocked my work. My OS is chef’s kiss now.”
Ariba Jahan, Head of Transformation, AI Product & Experience · September workshop
What you’ll understand by the end
You won’t leave with a setup someone else designed. You’ll understand the building blocks well enough to lead with them.
- How agentic AI actually works, and where it breaks. The concepts the whole field runs on, tested against your own work.
- Context management. Why AI forgets, and how to make it remember what matters.
- Skills and MCP. How agents connect to your tools, and how to create your own connections instead of relying on off-the-shelf ones.
- Automated loops. How to design work that runs on a schedule without you.
- Enterprise guardrails. What agents should and shouldn’t access, how to limit risk, and how to answer the security questions your leadership will ask.
Who this is for
Directors, VPs, Heads of Product and CPOs at companies where AI is not the core business, who need to lead AI adoption on their teams.
Product leaders who’ve used ChatGPT or Claude but haven’t yet built anything that runs on its own.
Leaders who want their teams working the same way, and who plan to roll out what they build.
What it isn’t
This workshop is not a prompt library or a done-for-you template. You are building, not watching. You’ll leave understanding what you built.
Your instructor
Polly Allen is the founder of AI Career Boost and a former Principal PM-Technical at Amazon Alexa AI, where she shipped the first generative AI answers on Alexa in 2020. She spent over a decade at Amazon and has 20+ years in tech across engineering and product leadership. She teaches the way she built: hands-on, grounded in what works inside large companies.
What’s included
- Four live, hands-on sessions (8 hours total) with Polly
- A working agentic system running on your own machine and your own work
- Session replays, so you can catch up or revisit any step
- The prompt library
- Portal access to all materials
Buying for a group?
If you’d like a private cohort run for your organization, write to [email protected] and we’ll set it up.
Our guarantee
Attend session 1. If the workshop is not what you expected, let us know before session 2 and we’ll refund you in full.
Expense it
Most participants use their company’s learning and development budget. Here’s an email you can send your manager:
Hi [Manager],
I’d like to attend the AI Player-Coach OS workshop, a hands-on program where product leaders build a working agentic AI system for themselves and their teams, including the guardrails for using it safely in an enterprise setting.
It’s four live sessions (8 hours), running October 6–15 or December 1–10, taught by Polly Allen, formerly Principal PM-Technical at Amazon Alexa AI. The cost is $1,500.
I’d come away able to lead our team’s AI adoption from hands-on experience, and with a system I can roll out to the team.
Can we use my L&D budget for this?
Thanks,
[Name]
Need an invoice for your company? Contact us.
Frequently asked questions
Do I need to know how to code?
Which run should I pick?
What do I need before we start?
What if my company restricts AI tools?
What if I miss a session?
How is this different from other AI courses?
I'm an AI Career Boost Blueprint participant. Do I need to buy this?
Does the workshop count toward the Blueprint?
AI Player-Coach OS
October 6, 8, 13 and 15 or December 1, 3, 8 and 10, 2026 · 9am–11am PT · Live on Zoom
Four live sessions. Eight hours. A working agentic system you understand well enough to lead with.
Enroll for October — $1,500