📣 She Almost Left Early. She Left With an Inside Advocate Instead.

👋 Hey Friends!

This one is for anyone trying to break into a new industry without a clear path in. By the end, you'll have a four-step strategy you can use at your next event to walk out with the right conversations, not just another LinkedIn connection. And if you’re trying to break into product management specifically, this applies directly to your job search, here’s why.

My friend Chelsea left an event this week convinced she had bombed it.

She hadn't. She walked out with an inside advocate at a company that never posts jobs, a direct line to the head of content, and a drinks invite from the person who could actually get her hired.

She just couldn't see it while it was happening.

Chelsea has been trying to break into a new role for a while. Sharp background, impressive internships, real experience. Her resume is not the problem.
I’ve been helping her navigate the search, it’s the same work I do with people in my mentorship sessions.

The event was hosted by Wattpad, which as it turns out is not just a fanfic site but a multi-million dollar content platform finding rising talent for future #1 Netflix shows and movies 🤯. She had been watching them for years. They never seem to have openings. So when this event came up, we went with a strategy. Not just to attend. To actually network.

She did not want to network. At every step of the evening: "I don't know what to say." "I'm going to embarrass myself." "Can we just watch the talk and leave?"

We found the host first. The head of content, 10 years at the company, the person who scaled the team to what it is today.

She introduced herself. Mentioned her background. Asked a real question about the direction of the company and what it's like being on the content team.

And the head of content told her exactly what they look for in candidates.

She also mentioned the team is growing soon and told her to stay in touch.

Then we sat down for the writing sprint. (I drafted most of this newsletter during that activity, which felt very on-brand.) We ended up across from someone on the Wattpad team who scouts new writing talent.

He and Chelsea started talking. Turns out they know half the same people. They clicked immediately. By the end of the night he had offered to try and get her in the door.

She is talented.
Her instincts are good.
Her background is real.

But she spent the entire evening talking herself out of every win as it happened.

This is what happens when you walk into a room already convinced you don't belong. When something good happens, you explain it away. She was just being polite. He was just being friendly. It didn't mean anything.

It meant something both times. She almost threw away two career-changing conversations because she was too nervous to believe they were real.

If any of this sounds familiar, the four steps below are what we used, and what you can do deliberately at your next networking event.

This is the one most people miss. If someone tells you what they look for and says stay in touch, that is not a brush-off.
That is an invitation.

If someone lights up talking to you and offers to help, they mean it.

The nerves will tell you it didn't count. It counts.

“I want to meet people” is not a strategy.
“I want to talk to whoever is leading product at this company” is.

Know one name before you walk in. Work towards that conversation first. If you’re targeting a PM role, that one name might be a Head of Product, a Senior PM, or a hiring manager at a company you’ve been tracking.

This is the highest leverage conversation in the room and most people skip it. The host usually knows the hiring landscape better than anyone.

In this case, the head of content shared exactly what she looks for and that the team is growing. That information does not exist anywhere online.

Not a pitch.
Not a resume summary.
A question that shows you have actually thought about the company.

She didn't lead with her background. She asked what the team was focused on. That one question opened the whole conversation. Let the other person talk. You will learn more and leave a better impression than anyone who spent the night selling themselves.

One more thing worth naming for PMs: the best rooms aren’t always the biggest ones. Product conferences, local PM meetups, and communities like Lenny’s or Mind the Product events are where your future hiring manager is also trying to learn, and is far more approachable than in a formal interview.

She went to one event with a strategy and left with an inside advocate at a company that never posts jobs.

- Stef

P.S. The event you’re dreading going to is probably the one you need to attend. If you’re trying to break into product management, I offer 1:1 mentorship sessions where we sharpen your story, map your target companies, and prep you for exactly the kinds of rooms Chelsea was in.