TheHigher-PayPlaybook
Use AI to target, pursue, and negotiate a higher-paying job.
An interactive digital job-search playbook that helps you turn your experience into a focused target, stronger materials, better access, confident interviews, and a defensible negotiation — using AI as the tool that gets you there.
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One quick step — this unlocks the full Playbook.
Start here.
This isn't something you need to finish in one sitting, and you don't need to read it cover to cover. Each part gives you something to do, the AI instructions to do it, an example of what good looks like, and an artifact you'll actually use in your search.
The rule of this playbook: you do the thinking. AI helps you research, interrogate, draft, test, and refine.
What you'll need:
- Your current résumé
- Access to an AI tool (ChatGPT, Claude, Gemini — any of them work)
- A place to save what you build as you go
Your path.
Seven parts, each building on what came before. Start with Target — click any part below to jump straight there.
Not sure what you'll end up with?
Decide what's worth pursuing.
Your experience may qualify you for more — and pay you more — than your current title suggests. Find the higher-paying roles it can credibly support before you spend a single hour applying to the wrong ones.
Your Target Role List — specific roles worth pursuing, each with a real compensation range behind it.
Show AI what you've got.
Use your résumé or work history to uncover what you can credibly sell — including value you've never put into words.
The How
"I'm going to describe my work history, one role at a time. Interview me — ask what problem I was trusted to solve, what decisions I was trusted to make, what got better, faster, cheaper, or more reliable because of my work, and where I created measurable value. One question at a time."
If AI starts summarizing you in generic terms instead of asking the next question, push it back to asking.
See an Example
Senior Manager, Sales Operations — B2B SaaS
Owned forecasting across 4 regions. Rebuilt the reporting process from scratch. Regularly presented to executive leadership. Reduced forecast variance enough that it changed how leadership planned quarterly targets.
Find where it can pay more.
Surface a short list of higher-paying paths, validate them against real evidence, then choose what you're actually pursuing.
The How
"Based on everything above, what's my obvious next-title move? Then show me 3–5 total paths, including at least two adjacent roles where this same capability may be valued — or paid — differently. One sentence each on why it fits."
"Compare what each path typically requires against what I've told you. Be honest about where I'm strong and where I'd be stretching."
"Here's what I found researching current postings and comp for my top 2–3 paths: [paste]. What patterns do you see? Separate what this evidence actually supports from anything that's still a guess."
AI doesn't know today's market from memory. It can only make sense of what you actually go find — real postings, real comp data.
See an Example
After surfacing paths and checking them against real postings and comp data:
Target Role List
Prove it on paper.
Not a generic AI résumé — a document built from real evidence, targeted to a real role, defensible line by line.
Your Targeted Résumé — built for a real job you're pursuing, defensible line by line.
Build your evidence.
Bring your current résumé. Use AI to uncover the accomplishments, scope, and results it doesn't show.
The How
"I'm going to describe a role or project. Interview me one question at a time: What changed because of this work? What was happening before you got involved? What did you personally own versus the team? How did people know it worked?"
Don't let AI answer its own questions for you. If you don't know a number, that's the answer — not a guess dressed up as one.
See an Example
Managed sales forecasting and reporting.
Owned forecasting across 4 regions. Rebuilt the reporting process. Worked directly with regional sales leaders. Reduced forecast variance. Presented to executive leadership.
Rebuilt forecasting and reporting across four regions, improving forecast accuracy and giving executive leadership greater visibility into pipeline performance.
Build it for the job.
Bring the job description. Match your evidence to what matters, build the résumé, then pressure-test it before you send it.
The How
"Here's the job description: [paste]. What is this person actually being hired to accomplish? Separate what's explicitly stated, what's reasonably implied, and what can't be determined from the posting alone."
"Compare my evidence against these priorities. Rate each Strong, Moderate, or Gap — don't soften a gap to make it look better."
"Select and rank what best supports this role. Turn it into concise résumé language — don't invent metrics I haven't given you. Then assemble it into a full résumé."
"Based only on this résumé, identify material reasons a hiring manager might hesitate — only where the résumé or job description actually supports it. Don't invent weaknesses for the sake of critique."
See an Example
A targeted excerpt after matching evidence to a Director, Revenue Operations posting:
Rebuilt forecasting and reporting infrastructure across 4 regions for a $40M B2B SaaS org, cutting forecast variance and giving the executive team real-time pipeline visibility ahead of board reporting.
Targeted Résumé ✓
Look beyond the obvious search.
Job boards are one source, not the whole market. Go direct to companies too, and spend your time where the signals are strongest.
Your Target Job List — actual companies and roles worth pursuing, weighted toward where the real openings are.
Build your target company list.
Use your Target Role List to identify companies where this role plausibly exists — not a job title search, a company search.
The How
"Based on my target role and adjacent targets, help me build a list of 15–20 companies where this role would plausibly exist. Mix company sizes, stages, and a few adjacent industries. For each one, give me one sentence on why it's a plausible fit."
"Which of these companies are you less certain are actually a fit right now — size, stage, or whether they'd realistically be hiring for this? Flag anything you're guessing on so I can verify it myself before spending time."
This is a starting list, not a final one — AI can suggest plausible companies but can't confirm who's actually hiring right now. Verify before you invest real time.
See an Example
For a Director, Revenue Operations target:
Check more than one source.
Company career pages, not just job boards. Then sort what you find by how much time it deserves — not every lead is worth equal effort.
The How
"Here's my target role and my target companies: [paste]. Give me 3–4 search strings I can actually use — variations on the role title, plus search operators that help me check company career pages directly (for example, restricting a search to one company's site)."
"Here's a posting I found: [paste]. Based on what's actually verifiable here — posting date, whether it appears elsewhere, how specific the requirements are, whether it's on the company's own career page — what signals suggest this is worth my time, and what's uncertain? Help me sort it as High Priority, Worth Pursuing, or Low Priority based only on what's observable, not a guess about whether it's real."
AI can't tell you whether a listing is real — only what's observable. Use it to sort where to spend your time, not to rule postings out. Company career pages often post roles before they reach the boards, so checking direct is one more good signal, not a rule.
See an Example
Posted 3 weeks ago, reposted twice, generic description, 400+ applicants — few verifiable signals of urgency
Apply if it takes five minutes — don't build your week around it
Posted 2 days ago, specific requirements, not yet cross-posted elsewhere
Apply now and prioritize follow-up — strong, verifiable signals
Target Job List
Be ready when opportunity finds you.
Not just LinkedIn. Opportunity shows up online, in writing, in conversation, and in the room — make sure your case is clear everywhere it might.
Your Positioning Kit — one clear case for your value, written and spoken, ready wherever someone encounters you.
Know how to talk about your value.
Turn your target, your evidence, and what you've learned about real opportunities into one clear position — not a rehearsed elevator pitch, something you can actually adapt.
The How
First, gather three things: your Target Role List, your résumé evidence, and 2–3 real postings for your target role.
"Here are 2–3 real postings for my target role: [paste]. What capabilities and outcomes come up repeatedly across these? What does the market actually seem to want, beyond the job title?"
"Here's what recurs across real postings, plus my Target Role List and résumé evidence: [paste all]. Build my core position: what I do, what I'm particularly good at, the evidence that makes that credible, and where I'm headed. Something I could say out loud, not corporate copy."
"Pressure-check this position: [paste]. What claim here isn't actually supported by my evidence? What's generic enough that another candidate in my field could say the exact same thing?"
This becomes your anchor — everything in step 2 is just this, adapted for a specific audience or format.
See an Example
Results-driven operations leader with a track record of success.
I build the forecasting and reporting infrastructure that lets B2B SaaS companies trust their own pipeline numbers — I've done it across four regions, and I'm looking to do it at the director level for a company scaling past $50M ARR.
Take that positioning into the market.
Adapt the same core position for every place opportunity actually shows up: online, in writing, one-to-one, in the room, and in the moment someone just asks.
The How
"Here's my core position: [paste]. Write a LinkedIn headline and About section from it."
"Now make it spoken — a 30-second introduction I could actually say out loud. Strip out anything that sounds written, not spoken."
"Now give me a one or two sentence version — for someone outside my field who just asked 'what do you do?' — plus a natural answer to 'what are you looking for right now?'"
"I'm attending [type of event]. My target is [role]. Here is my positioning and background. Help me develop three natural ways to answer 'What do you do?' depending on whether I'm speaking to a peer, a senior leader, or someone outside my function. Keep it conversational, not pitchy."
Same position, different audience, different delivery. You don't need to become a LinkedIn creator or a networking extrovert to use this — the point is having a ready answer, not performing one.
See an Example
Revenue Operations Leader | Scaling Forecasting & Pipeline Infrastructure for B2B SaaS
"I help B2B SaaS companies actually trust their pipeline numbers — I rebuild the forecasting process so leadership isn't flying blind."
Positioning Kit
Put yourself where opportunity can find you.
Applying is one door. It's not the only one — create a few more, digitally and in person.
Your Contact Map + Outreach Messages — specific people worth reaching, real messages ready to send, and places worth showing up.
Map your paths in.
For your top target companies, identify who's worth reaching — and where the relevant people actually show up in person.
The How
"Here's my target company and role: [paste]. Help me think through who's worth reaching — the hiring manager, a recruiter, people currently working in this function there, former colleagues who might know someone, alumni. For each type, suggest the most natural way in."
"Beyond messaging people directly, are there professional associations, industry events, alumni groups, or communities where people in this role or industry are likely to actually be? Suggest types of places to look, not guesses at specific events you can't verify."
AI can suggest categories of people and places — it can't tell you who's actually reachable or what's happening this month. That part is on you to confirm.
See an Example
Former colleague now works at target company, different team — natural, low-pressure ask for an intro to the hiring manager
Regional RevOps association hosts a monthly meetup — likely where peers and hiring managers in this function actually show up
Make the approach.
Turn your Positioning Kit into short, specific messages — plus a natural way to start a real conversation in person.
The How
"Here's my Positioning Kit and the person I'm reaching out to: [paste both]. Draft a short, specific outreach message — a few sentences, reference something real about them or their situation if I've given it to you, and end with a clear, low-effort ask."
"Now write a short follow-up I could send if I don't hear back in about a week — friendly, brief, not pushy."
"I'm going to a [type of event / association meeting]. Here's my positioning: [paste]. Help me think through 2–3 natural ways to start a conversation with someone relevant there, without it feeling like a pitch."
Your profile is the first thing most people check after a message lands — if Part 04 isn't finished yet, do that first.
See an Example
"Hi [Name] — saw you lead RevOps at [Company]. I'm working on the same kind of forecasting infrastructure problem at [current company] and would value 15 minutes to hear how you approached it there. Open to a quick call?"
"I've been rebuilding forecasting processes for a few years now — always curious how other people in RevOps think about it. What's kept you busiest lately?"
Contact Map + Outreach
Convert the conversation into an offer.
You already have the evidence. This turns it into stories you can actually tell — and practice you've actually done.
Your Interview Kit — real stories built around your target role, questions you're ready for, and questions worth asking back.
Build your story bank.
Turn your evidence into structured, interview-ready stories — the ones most likely to actually come up for this role.
The How
"Here's my Evidence Bank and my target role: [paste]. Identify the 5–6 stories most likely to come up for this specific role — based on what the job actually requires, not just my favorite accomplishments."
"Take this story: [paste one]. Structure it as Situation, Task, Action, Result — something I could actually say out loud in an interview. Concise, not a script."
"Pressure-test this story: what follow-up question would an interviewer likely ask about it? What's my honest answer?"
Repeat steps 2–3 for each of your 5–6 stories. Slower than one prompt, but you'll actually remember them under pressure.
See an Example
Rebuilt forecasting across 4 regions, reduced variance, presented to execs
"Forecasting was inconsistent across our four regions — leadership didn't trust the numbers going into planning. I rebuilt the process end to end, got regional leaders aligned on inputs, and within two quarters our variance was tight enough that leadership started using it directly in board reporting."
Anticipate and practice.
Predict what you'll actually be asked, rehearse out loud, and prepare what you'll ask them.
The How
"Here's the job description and my background: [paste]. What questions am I likely to be asked — both role-specific and about any gaps or transitions in my background?"
"Ask me one of those questions like you're actually interviewing me. Wait for my answer before responding."
"Critique that answer: was it specific enough? Did I actually answer the question asked? What would make it stronger — only flag things genuinely supported by what I said, don't invent weaknesses."
"Help me prepare 2–3 good questions to ask them — not generic ones, questions that show I've actually researched this specific role and company."
Repeat steps 2–3 for a few different questions. The critique should tell you what's true about the answer — not just be harder on you for the sake of it.
See an Example
"What's the company culture like?"
"I saw the team scaled quickly this year — what's been the biggest operational strain that's come with that growth?"
Interview Kit
Turn the offer into higher pay.
This is the whole point of the campaign. Know your number, and know exactly what to say when they push back.
Your Negotiation Plan — a target grounded in real evidence, and scripts ready for the actual conversation.
Know your number.
Ground your target in the market evidence you already gathered — not a guess, not just "more than I make now."
The How
"Here's my target role, level, and the market evidence I gathered earlier: [paste]. Help me determine a realistic target range and a walk-away point, based on this evidence."
"Here's the actual offer I received: [paste]. How does it compare to what I found? Where's my strongest leverage, and where's the real risk if I push further?"
AI can help you reason about your leverage — it doesn't know this company's actual room to move. Treat its read as a starting point, not a guarantee.
See an Example
$175K base
$180K–$210K, based on postings gathered in Part 01 — offer is below range, worth a counter
Build your scripts.
Know exactly what to say when the offer lands, when you counter, and when they push back.
The How
"Help me draft what I'd say when I receive the offer — buying time to consider it professionally, not committing on the spot."
"Here's my target range and their offer: [paste]. Draft a counter — anchored in the evidence I gathered, not just 'I was hoping for more.'"
"What are the most likely pushbacks to this counter, and how should I respond to each without sounding defensive?"
Practice saying these out loud before the real conversation — reading a script and saying it naturally are two different skills.
See an Example
"I was hoping for something a bit higher, is there any flexibility?"
"I'm excited about this role. Based on what I'm seeing for this level and scope in the current market, I was expecting closer to $195K. Is there room to move closer to that?"
Negotiation Plan
See it end to end.
Priya Anand — Senior Manager, Sales Operations at a mid-size B2B SaaS company — worked through every part of this Playbook. Here's what she built, part by part.
Selected components from Priya's targeted résumé:
Sample résumé — before and after
Why it changed: every "after" line names scope (4 regions, $40M org, 6 leaders), a result (cut variance, real-time visibility), and who it reached (executive leadership) — the "before" version could describe almost anyone in the role.
You built the system. Now run the search.
You now have the strategy, materials, messages, stories, and negotiation plan to pursue a higher-paying role intentionally.
How was the Playbook?
The Higher-Pay Playbook is yours to return to. Come back whenever you're ready to pursue a new role, strengthen your search, or make your next career move.