For senior operators weighing their next move

Find your next role before it’s written

Offtrail builds your shortlist of companies worth moving for, including ones that aren’t hiring yet, and shows who in your network can open the door.

Request Access How It Works

Your network wants to help. So why are you scrolling LinkedIn alone?

Asking your network if they know anyone hiring feels awkward because it is. Offtrail finds companies you’d actually want to work for, so instead of giving your peers homework, you can ask for targeted warm intros.

Inside your intelligence report

Five search paths, each with 5-10 targets

Offtrail maps where you’ve been, where you want to go, and where your strengths give you a natural edge. Then, it surfaces five specific directions for your next move.

Detailed briefs with org charts and contacts

Each brief tells you who to reach out to and what parts of your experience are most relevant. Plus leadership context, org structure, red flags, and questions to ask in the interview.

Rankings mapped to the priorities you set

You define what matters most: growth, mission, stability, prestige, culture, or flexibility. Then you’ll see how every company scores on each one, weighted the way you ranked them.

How it works

Our goal: turn an overwhelming search into one company a day, small enough that you’ll actually keep at it.

Offtrail maps your search paths

You fill out a short intake form about your background, goals, and priorities. Offtrail turns your intake into a handful of distinct directions for your next move.

We build your target list together

In a one-hour strategy session, Offtrail searches from multiple angles and surfaces real organizations that fit what you’re looking for. By the end, you’ll have 30 to 50 viable prospects to research and rank.

Offtrail researches and ranks your list

Each target gets filled in with the details you care about, then scored and ranked against your priorities. The strongest 20+ make it into your report, so the best fits rise to the top.

You start networking into your top matches

Your intelligence report gives you everything you need to request a warm intro: briefings on leadership, recommended contacts, and talking points built around your experience.

See how it works in detail →

Meet your guide

Hello! I’m Ben Jackson, a designer, bootstrapped founder, and AI product engineer. For over 20 years, I’ve built products and processes for companies like the New York Times, Vice Media, Peloton, and Atlassian.

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

Many of the best jobs still get filled this way. But most people don’t have the information to find the right companies and end up chasing whatever shows up on LinkedIn. I built Offtrail to close that gap and give you the same kind of leverage going in.

Check our mutuals →

Sharon M. Ravitch, Ph.D.

Professor of Practice, Penn GSE & Wharton Executive Education

Find the people who can open the door

Go from doomscrolling LinkedIn to landing warm intros into 20+ companies worth your time.

Request Access

Free to start · Pay only if you continue with a report

FAQ

How is this different from a recruiter or coach?

A recruiter is looking to fill a role at their client. A coach can help you reflect, assess options, or prep for interviews. Offtrail starts with your criteria and finds companies that match, whether or not they’re hiring for your role right now, along with everything you need to nail the warm intro.

Can I trust research done by AI?

Every report is built and reviewed by Ben, the founder of Offtrail, who’s spent years helping senior operators make big career moves. He’s battle-tested this system with over two dozen executives, using what he learned to fix bugs and sharpen the output. Every detail comes from a verifiable source (SEC filings, news articles, LinkedIn, company press releases) and is linked back so you can check it yourself.

Where do you find these companies?

Offtrail uses a search API built for this kind of research. AI agents search the web to find companies that match your criteria, then check their location and remote policy to make sure they’re viable options.

What happens after I apply?

If you qualify, Ben sends a sample of five search paths in about a week, with leadership context for each. If you continue with a report, you’ll meet with Ben for a strategy session to lock in your criteria, and your full intelligence report on 20+ companies arrives 5 business days after that.

Is there a cost to apply?

There’s no cost to apply. If your application is a fit, you’ll receive your search paths in about a week. You only pay if you choose to continue with the full report.

Is this confidential?

Yes. Offtrail doesn’t share your information or contact anyone on your behalf.