A strategist's approach to career moves

Your experience is the asset. This is the strategy for deploying it.

You share your background. I build your strategy.

Complete a 15-minute strategic intake about your career. Within 48 hours, get back a personalized playbook: territory maps, tailored narratives, real job postings scored for fit, and a week-by-week action plan. Built around your experience, not a template.

Territory Map
3-4 directions where your background has real leverage
Your Story, Tailored
A distinct narrative for each direction you pursue
Real Postings, Scored
Current openings at named companies, rated for fit
Action Plan
Week-by-week roadmap with targets, channels, search strings
See what you get How it works
Strategic stretch
Adjacent fit
Core fit

Most of the time you spend job searching is wasted. Here's why.

You send the same resume to 50 roles. You expect recruiters to connect the dots. You apply to things that are "close enough" and hope your experience speaks for itself. It doesn't. A recruiter or an AI screener spends seconds on your application. If the fit isn't obvious immediately, you're out. All that effort, gone.

This is a marketing problem. You need to make it brick-to-forehead obvious why you're the right person for a specific role at a specific company. That means fewer applications, not more. It means spending real time on 10 roles instead of skimming 100. And it means having a tailored case for each one, not a generic pitch you're hoping will land somewhere.

The playbook builds that for you: 3-4 focused territories where your background is strongest, a distinct narrative for each one, real job postings scored for fit, and a week-by-week plan so you're spending your time where it actually counts.

01

Know where you're strongest

Stop applying to everything that looks "close enough." The playbook identifies 3-4 territories where your experience gives you a real edge, so you focus your energy where you have the highest chance of landing.

02

Make the case obvious

A recruiter won't connect the dots for you. Each territory gets its own narrative: a specific, tailored story that makes you the obvious candidate, not someone who "could probably do it."

03

Spend your time where it counts

10 targeted, well-positioned applications beat 100 generic ones. Get target company lists, search strings, and a weekly rhythm built around the roles where you're actually competitive.

Here's exactly how it works

This isn't a quiz or a template. You share your real background. I run it through a proprietary AI engine built from 15+ years of strategy and innovation work. You get back a playbook that's actually yours.

01

You complete a strategic intake

A focused questionnaire about your career history, skills, what you've built, what excites you, and what constraints matter. Takes about 15 minutes. This is how I understand the full picture of your experience.

15 min questionnaire
→
02

My AI strategy engine analyzes your background

Your intake feeds into a custom-built AI system trained on my career strategy frameworks. It maps where your experience has real leverage, identifies career territories, builds positioning narratives, pulls real job postings scored for fit, and designs an action plan. This is how I deliver senior-strategist depth in hours, not weeks.

Delivered within 48 hours
→
03

You get a personalized playbook

An interactive strategy document built entirely around your background. Territory maps, positioning narratives, scored job postings, and a week-by-week plan. Open it on any device. Use it as your operating system for the search.

Interactive + PDF guide
See Pricing

Starting at $29. Includes strategic intake.

Why a personalized career strategy matters

Mid-career moves and career pivots are harder than entry-level ones. You have more experience, more options, and more at stake. That's exactly why you need a career direction assessment, not just another resume template.

Stop searching in five directions at once

Generalists try to keep every door open. Specialists wonder if they're stuck. The playbook gives both a framework for seeing where their experience creates the strongest case.

Your experience isn't the problem. Your framing is.

The same 12-year career can be told in completely different ways. Each territory gets a narrative that makes you the obvious candidate, not just someone with relevant experience.

Know where you're strongest before you apply

See at a glance where you're a core fit, where you're adjacent, and where you'd be making a stretch. That clarity changes how you spend your energy.

A roadmap, not a to-do list

At your level, 3 targeted conversations beat 30 applications. The playbook tells you exactly who to reach, through which channels, and on what timeline.

Replace anxiety with a system

You're good at what you do. But when it comes to your own career, the clarity disappears. The playbook applies real strategic rigor so you stop operating on instinct and start operating with a plan.

A strategy, not a wish

Most people approach a job search by reacting: scrolling, applying, hoping. The playbook gives you a clear direction and a system for getting there.

Sound familiar?

"I've built a strong career but I still can't explain what I do in a way that makes sense on a resume."

That's because your experience doesn't fit neatly into a job title. You've worked across functions, maybe across industries. Your versatility is a strength, but on a resume it reads as unfocused. You don't need to simplify your story. You need to tell it multiple ways, each one specific to a direction.

"I keep applying to roles I'm clearly qualified for and hearing nothing back."

When a recruiter scans 100 applicants who could all do the job, they're not connecting dots. They're looking for the candidate whose resume already makes the case. You're expecting them to see your potential. They're looking for someone who's already done the translation for them.

"Everyone keeps telling me to network. That's not a strategy."

It's not. Especially at your level, where the best roles rarely hit public boards and generic outreach gets ignored. You need a job search strategy with real targeting: specific companies, specific people, specific reasons for reaching out. Networking without positioning is just small talk.

"I'm great at my job. Why is figuring out my own next move the hardest thing I've ever done?"

Because you're too close to it. You can evaluate opportunities clearly when they're not yours, but your own career feels like an unsolvable puzzle. It's a framing problem. And framing problems are exactly what this playbook is built to solve.

"I asked ChatGPT to help with my resume and it sounded... fine. But I'm no closer to knowing what I should actually be going after."

AI tools can polish what you already have. The harder work is figuring out where your experience has the most leverage, building distinct narratives for each direction, and grounding it in what the market actually looks like. That's a synthesis problem, and it's what this tool is built for.

Read more: You Don't Have a Resume Problem. You Have a Direction Problem.

What your personalized playbook includes

After you complete the strategic intake, I analyze your background and build everything below around your specific experience, goals, and market reality. No templates. No generic advice. Two deliverables: an interactive digital playbook you can open on any device, plus The Job Seeker's Handbook, a comprehensive PDF guide with the strategic frameworks behind your plan.

Territory Mapping Included at $29

3-4 focused career territories, defined and mapped for you

Your strategy identifies the specific clusters of roles, industries, and company types where your background is strongest. Each territory comes with a clear narrative for why you belong, your credible way in, and an honest read on gaps. Visualized as concentric circles so you can see at a glance where you're a core fit, where you're adjacent, and where you're making a strategic stretch.

Territory mapping visualization showing concentric circles of career fit
Your Story — By Territory Full Playbook

A modular narrative system: your story, told for each direction

This is where the playbook delivers the most value. The same career can be told in very different ways. Your playbook includes a distinct positioning for each territory: the pitch, the resume emphasis, the story angles that make you the obvious candidate. A modular system you can deploy across your entire search, not one resume stretched across every opportunity.

Three distinct career narratives tailored to each territory
Territory Deep Dive Included at $29

Every territory broken down: fit, culture, target roles

Each territory gets a detailed profile: how strong your fit is, the culture of companies in the space, specific roles to target, and the narrative angle that makes you credible. A radar chart lets you compare territories across seven dimensions so you can make informed decisions about where to invest your energy.

Radar chart comparing three career territories across seven dimensions
Real Job Postings Full Playbook

Actual open roles, scored for fit

Not hypothetical roles. Real, current job postings at named companies matched to your seniority level and location. Each one scored for fit and annotated with why it connects to your profile. Organized by territory so you can see the live market for every direction you're considering.

Real job postings with fit scores and annotations
Search Strategy + Action Plan Full Playbook

Specific channels, target companies, and a weekly rhythm

LinkedIn boolean search strings you can copy and paste. A list of 10-15 target companies per territory. Channels beyond LinkedIn: niche job boards, industry newsletters, exec search firms, community events. Plus a week-by-week action plan so you know exactly what to do and when.

Search strategy with channel mix, target companies, and weekly action plan
Also included

The Job Seeker's Handbook

Your playbook gives you the personalized strategy. The Handbook gives you the methodology behind it: the frameworks for evaluating opportunities, the system for translating your experience across industries, the approach to building narratives that land with hiring managers. It's the reference you return to throughout your search, long after you've opened your playbook.

Included with every purchase as a downloadable PDF.

The Job Seeker's Handbook — strategic frameworks for career transitions, narrative building, and job search execution

Ready to see your territories?

See pricing

Delivered within 48 hours.

Why this career strategy tool is different

One resume, tweaked for every application

Distinct narratives for each direction, so every application makes a specific case

Scrolling job boards, hoping something fits

Territories grounded in real postings at real companies, scored for how well they match your background

ChatGPT gives you polished but generic advice

A professional strategic methodology, personalized to your experience, and grounded in live market data

See how it compares: Career Coach vs. Career Strategy Tool  |  Best Career Change Tools 2026

Where this comes from

Jessica Yankell
Jessica Yankell Innovation & Strategy Leader LinkedIn

I built The Job Seeker's Playbook because I kept watching smart people do their job search wrong.

Not because they lacked talent or experience. Because they were doing what everyone does: updating a resume, blasting applications, waiting for recruiters to connect the dots. Treating the search like a numbers game instead of a strategic problem.

I've spent 15 years in strategy and innovation consulting, advising Fortune 500 companies on growth, market entry, and new categories. I've also sat on the other side of the hiring table. Hundreds of candidates reviewed, dozens hired across consulting, innovation, insights, and brand strategy. I know what makes someone stop scrolling. And I know the gap between a strong background and a strong case.

That gap is where people get stuck. They have the track record. They just can't translate it into a story that lands for a specific role, at a specific company, solving a specific problem. So they cast a wide net with a generic pitch, and wonder why nothing moves.

I started seeing this pattern everywhere. Friends, colleagues, coaching clients. Strong careers, same broken playbook. I'd sit down with them, reframe their narrative, map the territory, rebuild the resume around the case they needed to make. It worked. Every time.

So I built frameworks around it. Then I built tools. The Job Seeker's Playbook is the result: a methodology built from real experience on both sides of the hiring table, now delivered with technology that makes personalized strategic depth possible at a speed that didn't exist before.

For what it's worth, I've made five major career moves of my own, every one through cold outreach. Consulting to client-side, startups to Fortune 500, across three continents. Every time, it came down to the same thing: knowing how to make the case before anyone asked me to. That's what this tool is built on.

15+
Years in strategy & innovation consulting
100s
Candidates interviewed, dozens hired
5
Career moves, all through cold outreach

What clients are saying

“

I'd been applying to everything and hearing nothing. The territory map showed me I was spreading myself across five directions when I had a really strong case for two. Within three weeks of focusing, I had four conversations going.

Senior Marketing Manager, career pivot
“

The strategy session changed how I talk about my career. I kept saying I was "a generalist" and she reframed my entire narrative around three specific territories where my experience is genuinely differentiated. I walked out with a completely different story.

VP Operations, exploring next move
“

I didn't expect real job postings scored for fit. I thought I'd get a framework and figure it out myself. Instead I opened the tool and there were actual roles at actual companies, ranked by how well they matched my background. That was the moment I realized this was different.

Director of Strategy, re-entering after a break
Get Territory Map — $29 or Get Full Playbook — $79

Get your playbook

After purchase, you'll receive a strategic intake questionnaire. Complete it in about 15 minutes. Within 48 hours, your personalized playbook is delivered.

Territory Map

3-4 career territories mapped and compared. Fit scores, gap analysis, and an honest brief for each direction. Plus The Job Seeker's Handbook (PDF).

Get Territory Map — $29
Most popular

Full Playbook

Everything in the Territory Map, plus real job postings scored for fit, narrative positioning by territory, sample resumes, and a search strategy with target companies.

Get Full Playbook — $79

Both include a strategic intake. You complete a 15-minute questionnaire, and your playbook is delivered within 48 hours.

Start with the Territory Map and upgrade anytime for $50.

Want to go deeper? Schedule a 1:1 strategy session to build your playbook together and pressure-test your positioning live.

Also available — coming soon

Resume Strategist
Tailored, territory-driven feedback on each resume version. Detailed strategic guidance on how to position your experience for each direction
Resume Comparator
Score your existing resume against specific job postings and get a gap analysis
Interview Prep Kit
Territory-tailored talking points, likely questions, and story bank for each direction

Stay in the loop

Occasional strategies for navigating your next career move.