Two quick things before we get into it:

• AI Arts & Crafts is this Friday, Oct 16 at 12:30pm PT. Online, playful, zero experience needed. Sign up →​
• I’m also opening a new AI for Coaches series. The first session is building your own Opportunity Scout, the same kind of system I’m writing about below. Four live sessions for coaches who want to build useful things with AI. See the series →​

I built myself a talent agent with AI

A few months ago, an AI agent told me I should apply for a job at OpenAI. This was surprising because I was not looking for a job.

I was on maternity leave. I had my own business. I was not browsing LinkedIn or sending out resumes. But the role it found was so good.

Executive Innovation Lead. Helping senior leaders figure out how AI should change the way their companies work. It pulled together an oddly specific combination of things I’ve spent my career doing: executive innovation work at IDEO, building companies, facilitating with senior teams, and now working hands-on with AI. It was also very well paid.

Basically: if I were going to break my “I am not looking for a job” rule for anything, this was exactly the kind of thing I’d break it for.

So I did.

I ended up in the interview process. Ultimately, the hiring leader left OpenAI and the process fizzled out. But the power of the opportunity finder stuck: I had not been looking for a job at all, and my AI had found one I genuinely would have loved. And this is why Career Scout is my favorite AI automation right now.

I basically gave myself an Ari Gold

The best analogy I have is Ari Gold from Entourage. Movie stars and professional athletes have people whose entire job is to look out into the world and ask:

What should my person be doing next? What opportunities are opening up? Who should they know? What’s worth pursuing? What isn’t?

Most of us obviously do not have that. But now I kind of do.

Every Wednesday morning, Career Scout goes out and looks for interesting opportunities for me.

Not just jobs. It looks for unusually good roles, paid partnerships, speaking opportunities, teaching gigs, media opportunities, interesting ways to work with AI companies, and other things that do not fit neatly into a job board. Then it sends me the handful it thinks are worth my attention. I genuinely look forward to the Wednesday email (sometimes I'll even run it on a Friday just for fun).

It started by looking for opportunities for my business

Originally, I wanted it to look for opportunities for Watch Me AI. Not leads, exactly. More like:

What is happening in the world right now that I might want to raise my hand for?

Maybe an AI company was launching a creator program. Maybe a conference was programming speakers. Maybe there was a company I genuinely loved that I could do something interesting with. Maybe someone was assembling faculty for a new program.

Then every once in a while, it would surface a job that was too good to ignore. OpenAI was the clearest example. At some point I realized the distinction between “career opportunities” and “business opportunities” was not that useful.

What I wanted was an agent looking for high-leverage opportunities for me.

ChatGPT already knew enough about me to be pretty good at this

This was not some giant engineering project. ChatGPT already knew an enormous amount about me.

It knew my work history, that I had spent four years at IDEO, the companies I had built, and what I was doing with Watch Me AI. It also knew I live in Seattle, have two tiny children, care a lot about flexibility, and am not particularly interested in getting on a plane three times a week. It knew roughly what kind of money would make a full-time role worth considering and which parts of my work I like.

So I gave it the job and had it run the search. Then I reacted:

No, those are not interesting.

This one is interesting. Why did you rank it so low?

Stop giving me generic consulting leads.

That sounds strategic, but it is an enterprise sales job.

Do not give me three mediocre things just because I asked for three.

If something has been sitting on the list for weeks and I keep ignoring it, maybe that is information.

Then I ran it again. And again. Within less than an hour, the output was good enough that I wanted it every week.

So I automated it.

If you’re a coach: the first session in my new AI for Coaches series is building your own Opportunity Scout. We’ll build it live, then use the next sessions to tackle other parts of your practice and business. See AI for Coaches →​

Every Wednesday, the agent goes looking without me

On Wednesday morning, I do not open ChatGPT and type, “Can you find opportunities for me?” Career Scout initiates the work itself.

It checks what has changed since last week, looks at current opportunities, checks my inbox, and can look at my network to see whether I know someone at a company. It also remembers things it found previously and whether they are getting more interesting, less interesting, or have gone stale.

Then it sends me something like:

HERO OPPORTUNITY​
The one thing it thinks deserves the most attention.

THE BENCH​
A couple of other things worth knowing about.

NETWORK WARMING​
People where there is a genuine reason to reconnect right now.

DO NOW / DO IF CAPACITY / WATCH

That last part matters. I do not need an AI that creates twelve new tasks for me every Wednesday. I want it to have an opinion.

When it finds something good, I can put it to work with one reply

This may be my favorite part. Career Scout finds something, and I read it and think:

Ooh. Yes. That one.

And I respond with something like:

“Yep, pursue #1.”

Then it can start doing the work that normally follows discovery: research the company, figure out who runs the team, look through my network for a warm path, and check whether I have emailed anyone there before.

It can work out why I am a credible fit, draft the note, help tailor my positioning, prep me for the conversation, and keep track of what happens next.

So instead of:

Find opportunity → research → evaluate → find contact → figure out angle → write outreach → follow up

The human part becomes:

Yes. That one.

That feels very close to having an Ari Gold.

The real magic is that I do not have to be looking

Lots of AI automations save time. That is useful. But Career Scout does something I find much more interesting: it creates serendipity.

I do not have to decide, “I am now looking for a new job,” before I discover a fantastic job. I do not have to decide, “I need to find a speaking opportunity,” before one appears. I do not have to spend an afternoon poking around the internet trying to figure out what I am missing.

There is just something out there looking on my behalf. Most of the time, I keep doing exactly what I was already doing. But occasionally it taps me on the shoulder and says:

You were not looking for this. But I think you are going to want to see it.

That feels like a fundamentally different kind of AI assistant. Not just one that does the work you already know needs doing, but one that develops an ongoing point of view about what might be worth doing next.

And apparently, mine works Wednesdays.

Want your own? I made a short guide to building an Opportunity Scout in ChatGPT or Claude.

​Build your own Opportunity Scout →​

If you’re a coach and want to build one with me live, it’s the first session in my new AI for Coaches series.

​See AI for Coaches →​

PS: Two things coming up

AI Arts & Crafts is this Friday

Come make something weird, delightful, or surprisingly beautiful with AI.

​Come make something with us →​

Or, book me for your team at work. Private AI sessions start at $750. Just respond to this email.

AI for Coaches

I’m putting together a new four-part live series for coaches who want to build useful things with AI. The first session is building your own Opportunity Scout, the same kind of system in this newsletter.

We’ll build practical tools you can use in your coaching practice and business, with recordings and AI Mollie afterward so you can keep asking questions even if you miss something live.

​See the series / join →​

Until next week,

Mollie