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

How it works

Offtrail flips the job search on its head

Instead of starting with a list of open roles, you start with a list of people to meet at the places you’d love to work.

Step 1

Search Plan

For when it’s time for a better seat at a brand new table, but the thought of asking your network “know anyone hiring?” makes you lose your appetite.

We start with a conversation about where you are, what matters to you, and where you can see yourself thriving. Then we nail down the criteria for your next move (size, stage, industry, culture, you name it) and build the plan around them.

You leave with

Your plan: which of 20+ companies to prioritize, who to talk to at each one, who in your network can make the intro, and what to say when they do.

$750

Refundable in full until your strategy session.

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Step 2

Outreach Intensive

For when you’re ready to get the first wave of intros out the door.

In one working session, we shape a forwardable email for every leader on your list. I bring the first drafts; you make them yours. For each one, we find your strongest mutual connection. Then you ask them for the warm intro, from your own accounts.

You leave with

Your first wave of intros, drafted and ready to send, plus your own CRM, connected to Claude and loaded with the matches from your target list.

$2,500

Your $750 from the Search Plan credits toward it.

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Inside your plan

5 search paths, each with 5-10 targets

Offtrail weighs where you’ve been against where you want to go, then picks the five paths where your experience gives you the strongest case.

Briefs with org charts and contacts

Each brief tells you who to approach and what parts of your experience to lead with. Plus who runs the place, red flags, and questions to ask in the interview.

Rankings mapped to the priorities you set

You set what matters most: growth, mission, stability, prestige, culture, or flexibility. Your matches score against each priority, weighted how you ranked them.

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

Questions

A recruiter is paid by the employer, so the search starts from their 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.

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.

Ben builds every plan himself, after years of helping executives make big career moves and running this system with more than two dozen of them. Every detail comes from a named source, like SEC filings, news, LinkedIn, or company press releases, and links back so you can check it yourself.

The fit call is free and quick: we figure out whether Offtrail is right for your search. If it is, you start that day: first a conversation about what you want from your next move, then a 90-minute strategy session where we build your target list together. Your plan, covering 20+ companies, lands five business days later, followed by a 30-minute debrief to map your first outreach.

The fit call is free. The Search Plan is $750, paid when you start and refundable in full until your strategy session. The Outreach Intensive is $2,500, with your $750 credited toward it.

No. The plan stands on its own, and plenty of people run the outreach themselves. The Outreach Intensive is there for when you want the first wave sent with someone at the table.

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

Start with a 15-minute call

Tell me where your search stands, I’ll tell you whether I can help. If I can’t, I’ll say so on the call.

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