Your fit call is booked. Until then, here’s a look at how Offtrail can accelerate your search.

A guided, networked search for senior executives

Find your next leadership role before it’s written

Offtrail is what you do instead of applying. It maps the network you already have, finds the companies you’d actually join, and gets you in through the right door with a warm intro.

See How It Works
Built with 25+ senior leaders from companies like The New York Times, Meta, and Microsoft.
The New York Times Meta Microsoft Adobe Uber Peacock

Where did your best role come from?

Odds are it wasn’t through a job board. Someone made a call, and you walked in with standing instead of landing in the slush pile.

So why does the standard search work the opposite way?

It asks someone who spent a decade building relationships and expertise to get in line with everyone else. It leaves you scrolling LinkedIn for roles that were never going to come to you. It flattens a career of earned reputation into one more resume in the stack.

Worse, it pushes you toward the ask you dread: “know anyone hiring?” It’s vague, it’s easy to ignore, and it hands your network homework.

Whether you’ve outgrown your seat or regret your last move, that dread is what’s stopping you from finding your next role.

Offtrail is what you do instead of applying. You already put a specialist on every other high-stakes move: comp, contracts, your portfolio. Offtrail maps the network you’ve built and finds the companies you’d actually join. Then you walk in, introduced by someone who vouches for you.

Meet your guide

Hello! I’m Ben Jackson. For over 20 years, I’ve helped places like the New York Times, Vice Media, Peloton, Atlassian, and Swing Left build great products and great cultures.

Earlier in my career, when I joined Vice as Director of Mobile, I got the job through my network. I was the only candidate, and had leverage to shape the role and negotiate a great offer.

I’ve spent ten years helping people be happier at work, and kept meeting leaders who never got that lucky: good people stuck in roles they’d outgrown, because they couldn’t see what was out there. When they burn out, all of us pay the price. I built Offtrail so leaders like you can own their next moves, and so every organization is led by someone excited to be there.

Check our mutuals →
Ben Jackson
Sharon M. Ravitch

Sharon M. Ravitch, Ph.D.

Professor of Practice, Penn GSE & Wharton Executive Education

“For most top managers and senior leaders, the job search is over before it starts. They’re at the top of their careers, and haven’t looked for a job in a decade or more.

“Offtrail surfaces opportunities you would not be able to find on your own, and working with Ben means there’s someone holding your vision when you’re scared. I have recommended it to multiple groups and individuals I lead and coach, and I’ll keep recommending it, one person and organization at a time.”

Your network wants to help. Make it easy for them.

“Know anyone hiring?” feels awkward because it is. Instead of handing your friends homework, give them an easy way to help. Your plan tees up 20+ companies worth a warm intro.

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