The Boss Request Template

If your company has an AI training budget, this one is for you. Short, Slack, and full-length email templates for asking your manager to expense an AI Pro subscription, plus a note about the team discount if you'd rather bring everyone along.

If you think your AI training budget covers access to this site, here’s an email request form. Note that I also do discounts for teams if you want access for everyone! Either way, let’s keep our eye on the ball…

The Short Version

Hi [Manager's name],
Asking for approval on a $499/year subscription to The AI Pro (https://ai.bigmachine.io), a senior-developer community focused on shipping production-quality code with AI tools. It's run by Rob Conery (The Imposter's Handbook, ex-Microsoft VS Code team), explicitly aimed at craftsmanship over hype.
Cheaper than one conference ticket, continuous (not a one-shot course), and directly relevant to how we already work. I'll share what I'm learning back with the team. (There's also a 20% team discount if you'd rather roll it out broader.)
Can I expense it?
Thanks, [Your name]

The Slack Version

"Hey, quick ask. There's a community called The AI Pro that's $499/year, run by Rob Conery who wrote The Imposter's Handbook. It's senior-developer focused, explicitly anti-hype, all about shipping good code with AI rather than vibe coding. Less than a conference ticket, I'd be in it year-round, and I'd write up what I'm learning for the team. Can I expense it?"

The Full Version

Hi [Manager's name],
I want to request approval to expense an annual subscription to The AI Pro (https://ai.bigmachine.io), a community focused on AI-assisted coding for senior developers. It's $499/year (or $69/month if you'd prefer monthly).
Here's why this is worth it:
AI tools are now part of how we ship. We're already using [Copilot / Cursor / Claude Code / your tool here] on [project / team]. The gap between "using it" and "using it well" is the difference between code that compounds and code that creates tech debt. I want to close that gap deliberately.
Most AI content online is noise. Influencer threads, hype videos, "10x your productivity" promises. The AI Pro is run by Rob Conery, who wrote The Imposter's Handbook (30,000+ copies sold), spent years at Microsoft on the VS Code team working with Copilot, and has 25 years of developer education behind him. He's explicitly anti-hype and anti-vibe-coding. The focus is craftsmanship: shipping maintainable, reviewable code with AI as a tool, not as a slot machine.
It's built for senior developers. No intro material, no "what is a function" lessons. The audience is people like me who already know how to architect systems and want to integrate AI into that practice without losing rigor.
What I'll bring back to the team:
Concrete patterns for code review when AI is in the loop
Workflows for using agents on real codebases without breaking things
A clearer point of view on where AI helps and where it hurts
Specific techniques I can document and share in our [team channel / standup / wiki]
Cost comparison: $499/yr is less than one day of consulting, roughly a third of a conference ticket (without travel), and less than half of a single one-time online course. It's also a continuous resource, not a single training event that fades from memory in three months.
I'm happy to write up a short summary of what I'm learning every [month / quarter] so the team gets compounding value out of this, not just me.
Can you approve this for [Q1 / this quarter / 2026 training budget]?
Thanks, [Your name]
P.S. If you'd rather get the whole team on this, there's a 20% team discount available. At that rate it's about $399/seat/year, which still beats almost any other training option line-for-line. Happy to put together a list of who on the team would benefit if you want to go that route.

Anticipated objections and how to answer them

"We already pay for [Copilot / Cursor / Claude Code]."

Right, and that's exactly why this matters. We're paying for the tool. This is training on how to get the most out of the tool. They're complementary, not redundant.

"Can't you just learn this from free content?"

I can, and I've been trying. The problem is the signal-to-noise ratio is brutal. I'd rather pay $499 for curated content from someone with 25 years in dev education than spend 25 hours of company time sorting through YouTube videos.

"Why not a one-time course instead?"

The space is moving too fast. A course recorded six months ago is already stale. A community keeps up with what's actually working.

"Try it for a month first?"

Happy to. The monthly is $69. If after 30 days it's not delivering, I'll cancel and switch to something else.

"What about the rest of the team?"

There's a 20% team discount, so we'd be looking at roughly $399/seat/year. The honest answer is everyone on the team using AI tools daily would benefit. The bigger win is that we'd build shared vocabulary and shared workflows around AI-assisted code, which is hard to do when one person is reading blogs and another is watching YouTube. If you want, I can put together a short list of who I think would get the most out of it and we can start there.