Find your next leadership role before it’s written
Define and deliver a hit list of 20 places you’d love to work, enriched with AI and ready for outreach.
AI-Enriched Career Intelligence for Senior Executives
A focused, 1-hour workshop to define your ideal leadership role, discover places you’ll want to work, and enrich the data with valuable context.
What you get
90 minutes of live, one-on-one coaching
Spark inspiration as we test hypotheses, look at matches, and refine your criteria until we find signal.
Know what you’re looking for (and how to explain it)
Define crisp talking points so you can explain what you’re looking for to anyone in 30 seconds.
20+ targeted prospects with valuable context
Enriched with information on benefits, investors, market position, press, and LinkedIn profiles.
A briefing on each match to inform your outreach
Recent news, intel on decision-makers, and angles for outreach to help you open the conversation.
What you pay
For the first 20 clients, Offtrail will be sold on a Pay What You Want basis. You’ll receive a payment link with your results. There is no minimum, and you’ll be able to pay whatever you feel the service was worth.
Is your VP or C-level job search stuck?
If the following sound familiar, this service is for you:
You’re ready to move on, but work is too chaotic
You’ve already tapped your executive recruiter network
You’re unsure if it’s better to jump ship or hold on
You’re looking discreetly, staying under the radar
You’re sick of aimlessly scrolling LinkedIn
How it works
Define hypotheses for your executive search
We meet for a 1-hour workshop to clarify what you’re looking for
Filter potential employers and enrich the data
Proprietary AI agents find, enrich, and rank your personalized matches
Use the results to jumpstart your search
You get a hit list of 20+ companies, with briefings on each one
Meet your guide
Hello! 👋🏻 I’m Ben Jackson. When I’m not coaching executives, I run Hear Me Out, a management consulting firm that helps teams become more effective by running confidential listening tours. Through hundreds of interviews, I’ve learned to spot the details that separate good places to work from ones that just look good on paper.
Check our mutuals →
FAQ
VP and C-suite leaders who know it’s time to move but don’t have time to research opportunities. You should be clear on the direction (role, industry, stage) but unsure where to look.
Pay whatever you think it’s worth. This is a public beta—decide your own price based on the value you get.
Nope. What you see is what you get.
You’ll receive a checkout link with your hit list.
You’ll receive your hit list within 24 hours of our workshop.
Yes. Your search is completely private. We don’t share your info or contact anyone on your behalf.
A structured document, with each organization profiled separately. Each profile includes a TL;DR section, a company overview, strategic context, the key decision-maker with LinkedIn profile, recent funding or milestones, relevant interview excerpts or content, and an angle for your outreach.
Executive recruiters match you to their clients’ existing roles. This finds organizations where you’d thrive, whether or not they’re actively hiring. You control the timing and approach.
The process includes a structured interview, live coaching, and proprietary AI research agents. It will help you define what you want 5x faster, uncover 10x the employers, and gather 50x more context on each one. You won’t get the same results by just dropping your search criteria into ChatGPT.
That’s exactly what the workshop is for. We’ll work through your criteria together and test different filters until the matches clarify what you’re actually looking for.
We refine your search criteria during the workshop to validate the approach is working. You’ll see sample matches before we finish, so we can adjust the filters until they surface promising results.
You’ll complete a brief intake survey before our workshop covering your background, preferences, and deal-breakers. We’ll refine everything live during our session.
Completely. Every filter, every data point, and every match is based on your specific criteria.
Yes. If the first pass doesn’t feel right, we’ll adjust course and run it again.
Yes, as an optional add-on. If you need help with this, let me know and we can schedule a separate session to research decision-makers and draft some outreach emails.