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.

Request Access How It Works

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 leverage 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’s slow, it’s beneath you, and it leaves you scrolling LinkedIn for roles that were never going to come to you, waiting behind people with no track record. It flattens a career of earned reputation into one more resume in the stack.

Worse, it pushes you toward the one move you hate: with no target list, networking collapses into a simple “know anyone hiring?” That kind of vague ask is easy to ignore, and it turns someone who runs teams and closes deals into someone asking for a favor.

That dread is what’s really stopping you from finding your next role.

Whether you’ve been at the same place for years or just made a move you regret, you know it’s time, but you haven’t started.

Offtrail is what you do instead of applying. You don’t stand in line and you don’t ask for favors. You map the network you’ve already built, find the companies you’d actually join, and walk in through the right door, from the same position of strength you bring to everything else.

Inside your plan

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

Your access survey and LinkedIn profile give Offtrail what it needs to draft five distinct directions for your next move. You’ll see the drafts at your free fit call, before you’ve paid anything.

We build your target list together

The 90-minute strategy session opens with what you actually want from your next move and what’s held you back so far. Then you finalize your paths with Ben, Offtrail searches each one live, and you come away with 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 plan, so the best fits rise to the top.

You start networking into your top matches

Your plan gives you everything you need to nail the ask: briefings on leadership, recommended contacts, and talking points built around your experience.

See how it works in detail →

Meet the founder

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 →

Sharon M. Ravitch, Ph.D.

Professor of Practice, Penn GSE & Wharton Executive Education

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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FAQ

How is this different from a recruiter or coach?

A recruiter is paid by the company, so the search starts from the employer’s criteria and ends at their open role. A coach can help you reflect, assess options, or prep for interviews. With Offtrail, you’re the client: the research starts from your criteria and finds the companies that match, whether or not they’re hiring right now, along with everything you need to nail the warm intro.

Can I trust research done by AI?

Every plan is built and reviewed by Ben, the founder of Offtrail, who’s spent years helping executives make big career moves. He’s battle-tested this system with over two dozen of them, 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 your survey qualifies, you book a free fit call with Ben, who drafts your five search paths beforehand and shares them at the end of the call. If you move forward, you book a 90-minute strategy session, where you finalize your paths and build your target list together. Your full plan, covering 20+ companies, arrives 5 business days later, followed by a 30-minute debrief to map out your first outreach.

Is there a cost to apply?

No. Applying and the fit call are free, and you’ll see your draft search paths before you decide. The full engagement is $750, paid when you choose to start, refundable in full until your strategy session.

Is Offtrail a recruiter or employment agency?

No. We never contact employers, submit your materials, or arrange interviews, and employers don’t pay us anything. Offtrail does the research; you and your network do the reaching out.

Is this confidential?

Yes. Offtrail doesn’t share your information or contact anyone on your behalf. See our Terms & Conditions.