How it works

Here’s how an Offtrail search actually runs

Offtrail flips the usual job-search logic. Instead of starting with a list of open roles, it starts with a list of people to meet.

The goal is to help you network strategically with targeted outreach to a small list of people who could open the door to your next big move.

But who are these people you need to meet? They’re probably the leaders at the places you’d most want to work. And unless you have a team of research assistants on call, finding them means building a target list: a short roster of pre-vetted organizations you can see yourself thriving at. With this list, instead of waiting for opportunities to appear, you can build relationships, set up alerts, and stay visible to your future coworkers.

Step 1

We map your search paths

To build a target list, you need a search path: specific criteria that narrow the field. Which paths make sense depends on what you’re looking for, so that’s where we begin.

Before committing to Offtrail, you share your preferences: size, stage, and industry, the titles you’d consider, and any must-haves or dealbreakers. You also rank six fit factors in order of importance to you: growth, mission, stability, prestige, culture, and flexibility.

Multi-select dropdowns for remote policy and customer type, with a drag-to-rank list of six fit factors. — The intake form, with fit factors ranked in priority order.

Offtrail takes your intake and your LinkedIn profile, and turns them into a handful of distinct directions for your next move. Each search path names a kind of organization, with examples to anchor the search, plus a target role and why your experience gives you an edge. Something like:

“VP of Marketing or CMO at a D2C startup that raised a Series A to C in the past 2 years, has at least 75 employees, and a product that benefits school-age children or working parents. Examples: Lovevery, Outschool, KiwiCo, Greenlight, and Yoto. Most candidates here come from e-comm. Experience with parent-buyer, child-user audiences, where the purchase decision and the product experience are split, is rare.”

Once your paths are ready, you and Ben review them together in a 20-minute session. The test for each one is a vibe check: do the organizations it surfaces feel like places you’d want to work? You only commission a report once the answer is yes.

Step 2

We build your target list together

When you commission your report, we book a one-hour strategy session. Offtrail searches each path from a half-dozen angles and pulls back real organizations that fit. After each wave of searches, we review the matches together, including location and remote policy, and keep only the ones you say are worth pursuing. By the end, you’ll have 30 to 50 real, viable prospects to research and rank.

Step 3

Offtrail researches and ranks your target list

Each target gets filled in with what matters to you: benefits and parental leave, management culture, recent product announcements, notable hires. The goal is to surface everything we need to tell which organizations are the best fits for your next move.

Then, Offtrail ranks the list. Every target is graded on the same rubric against the must-haves, dealbreakers, and fit factors you ranked during intake, and the scores are weighted so your top priority counts six times your last.

Company scorecard with six fit dimensions (growth, mission, stability, prestige, culture, flexibility), each rated and sourced. — Targets scored and weighted against your ranked priorities.

Step 4

Your intelligence report takes shape

Every target that clears the bar gets a detailed briefing: full leadership with LinkedIn profiles, recommended contacts, and talking points for outreach. A headline scan turns up any red flags on the organization, its founders, or its top investors.

For job boards like Greenhouse, Lever, and Ashby, Offtrail scans every open role to find direct fits, or postings that signal growth on a team you’d want to join.

Hiring intelligence panel listing open roles with notes on what each signals about team growth and org structure. — Hiring intelligence from Greenhouse, Lever, and Ashby, with signal roles flagged.

Step 5

You start networking into your top matches

Your finished report arrives five business days after the strategy session, and you and Ben meet for a 30-minute debrief: a walk through your top-ranked targets that ends with a clear plan for your first outreach.

The way to land a warm intro with a busy executive is a forwardable email: a short, personal note sent on by a trusted mutual connection. A good one lowers the cost of helping you to almost zero, turning what could be an awkward ask into a mutual favor. (For tips and examples, read Chris Fralic, Roy Bahat, and Wes Kao.)

For each target, you pull up the recommended contacts and start working out who can introduce you. You can even hand that research to AI by copying a ready-made prompt into Claude in Chrome or the ChatGPT Atlas browser.

Outreach panel showing recommended decision-makers and personalized talking points for the warm intro. — Recommended contacts with personalized talking points.

Once your mutual agrees to make the connection, you use the briefing from your intelligence report to write the forwardable email. Each briefing comes with recommended talking points, so you can lead with the experience most relevant to the leader you’re reaching out to.

Beyond the report

Own the system, not just the list

Most people run a search like this out of spreadsheets and memory. Ben can build you something better: a CRM in your own account loaded with your targets, connected to Claude, with the playbooks and runbook to operate it yourself. It outlives this search and keeps your network warm for the next one. Details and pricing →

Sharon M. Ravitch, Ph.D.

Professor of Practice, Penn GSE & Wharton Executive Education

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