The Startup of You (AI Edition)
A Mid-Career Playbook for Using AI to Design Your Next Role With Leverage, Learning, and Optionality
Note to Founders
You’ve probably seen the posts.
Smart, experienced operators - laid off.
Long LinkedIn updates.
Gracious exits.
Uncertain next steps.
This piece isn’t written directly for you. But it’s for someone you know.
Someone on your team.
Someone in your feed.
Someone you used to be.
I was one of them.
And chances are, you were too - before you stepped into the shoes of a founder.
This article is for the operator in transition.
The one whose title disappeared, but whose value hasn’t.
The one looking for what’s next - without a playbook.
I wrote this to help them use AI to rebuild with intention.
To find or create the role that actually fits.
To learn systems while they search - so they stay in motion, not in waiting.
If that’s someone in your world, share it.
If it’s someone on your team who may be at a crossroads, send it now.
If you recognize your past self in these pages, keep reading.
This isn’t a resume guide.
It’s a career operating model - built with clarity, leverage, and optionality.
And it’s designed to help them (or you) build forward.
Part 1: Stop Searching, Start Engineering
Eight years ago, I left a senior role without a backup plan.
Three months before my first child was born, I stepped out of a role that no longer made sense. There was no next title waiting. No roadmap for what came next. What followed was a season of reorientation. It didn’t look like building a company at first. It looked like building a system that made sense for how I wanted to live, work, and create.
That system became Growth by Design.
Today, I help founders scale with clarity through my firm GetFresh Ventures.
But lately, I’ve spent more time guiding operators.
Leaders who’ve built teams, owned outcomes, solved hard problems—now holding space between what was and what’s next. Some exited roles on their own. Others moved on during a layoff or shift. Each one arrived with the same quiet tension:
“I want to keep working. I want to do work that matters. I just don’t want to give my whole life to a machine I no longer believe in.”
This is a moment with its own physics. Time slows down. Calendars open up. You begin asking different questions.
Where do I actually do my best work?
What type of team makes me better?
What structure lets me build a life, not just a job?
These are design questions. They require architecture, not reaction.
And you’re equipped to build the answer.
You’ve led systems. You’ve carried teams. You’ve figured it out mid-flight more times than anyone saw. The difference now is that the system you’re building is you.
Greg Isenberg said this recently:
“Millions of white collar jobs will disappear once the productivity gains of AI play out… but the top 1% who master AI will create 10x output and dominate the future of work.”
That future is not abstract. It’s already reshaping org charts, incentives, and decision-making inside the companies you’ve helped build.
But it’s also creating something else:
“Thousands of smart people now have severance checks, free time, and a chip on their shoulder… and realize building a business costs less than a decent laptop.”
That insight opens up a broader frame.
Because whether you start a company, go fractional, or join a team—you are now the builder. Your experience is the foundation. Your next role is the spec. The process of finding it is the go-to-market motion.
This next chapter is not a waiting game. It’s a system design.
You’ll use AI to define your role with more clarity
You’ll use AI to research and surface the right companies at the right moments
You’ll use AI to scale your messaging and open new doors
You’ll create a structure that grows your options, not just your inbox
This isn’t a call to reinvent yourself. It’s a call to rebuild with intention.
We begin by building your operating model.
Part 2: Growth by Design for People, Not Just Startups
Every founder I’ve worked with comes to a moment where clarity becomes non-negotiable.
Not a new tool. Not a vision deck.
A clear system.
They’re growing. But the execution is starting to break. Their messaging is muddy. Their team is misaligned. Their days feel reactive. They’ve outgrown their seat-of-the-pants stage.
That’s when we bring in Growth by Design.
It’s a framework for building on purpose.
Define the real value.
Design the system around what works.
Create structure that scales without chaos.
What surprised me is how often the same system works when a career hits that same pressure point.
A mid-career shift isn’t just a fork in the road. It’s a forcing function.
You’re no longer making decisions from energy alone.
You’re making them from experience.
And experience deserves an engine.
So we start the same way we start with companies: with a GTM system.
You define your offer—who you are, what you solve, what you want to be known for
You map the buyers—companies going through transitions where your skills make a measurable difference
You shape your positioning—language that lands with the right people and builds pull
You design a system—one that runs even when you're not hustling
Growth by Design turns ideas into motion.
It gives structure to momentum.
And it makes sure you’re building with alignment, not drift.
This approach works for people the same way it works for startups:
Your experience becomes a signal, not a list
Your role becomes a spec, not a label
Your outreach becomes a system, not a task
Your journey becomes repeatable, not accidental
Each artifact becomes part of a machine.
Each tool you touch—GPT, Claude, Clay, Notion, LinkedIn—becomes part of a GTM loop.
And in that loop, your career stops feeling like a search.
It starts operating like a launch.
Part 3: Define the Role You’re Built For (Using AI Projects)
You don’t need to guess what role to chase.
You’ve already done the work—years of it.
The next step is turning that history into signal.
This is where your AI workspace begins.
Set Up Your Project: Your Career GTM System
Open GPT-4 or Claude. Create a new “Project.”
Name it something simple: Career GTM, Next Chapter, or Startup of Me.
Now start uploading.
This is your raw material:
Your resume(s)
Performance reviews
LinkedIn profile
Case studies, presentations, screenshots
Draft bios, About pages, cover letters
Emails you’re proud of
Weekly updates from past roles
One-pagers or product specs you wrote
Anything that shows your way of thinking and executing
You're not trying to impress anyone yet.
You're feeding the system what it needs to reflect you back—accurately, with pattern and clarity.
This is your personal data set.
AI will help you extract the themes.
Run These Core Prompts to Extract Signal
Once your project is populated, start running prompts like:
“What are the 5–7 recurring strengths you notice across my work artifacts?”
“Describe the type of work where I seem to have the most momentum or clarity.”
“List three types of roles or environments where these strengths would compound.”
“Summarize my positioning in one sentence based on what you see here.”
“Draft a role spec for a job that aligns with the themes, skills, and work patterns shown in these documents.”
You can also ask it to:
Translate your experience into startup, enterprise, or AI-native environments
Show you how your skills might map to fractional work or transition-stage companies
Compare your current LinkedIn summary to your actual strengths and propose improvements
This is not reflection for its own sake.
This is structured self-definition.
You're not reinventing.
You're re-surfacing.
What You’re Building
By the end of this section, your GPT/Claude project will contain:
A one-line summary of your career positioning
A 3–5 sentence version you’ll use in outreach and interviews
A list of job titles, role types, or hybrid models that fit you
A draft “role spec” that describes your ideal work week, the problems you want to solve, and the kind of org structure where you thrive
A shortlist of industries, company types, or inflection points where your experience creates leverage
You’ll use all of this in every future step:
In messaging. In personalization. In finding the right leaders to talk to.
But most importantly:
This becomes your clarity anchor.
Every tool we introduce next flows from this foundation.
Part 4: Build Your Personal GTM System in AI
Your project is now loaded with context.
You’ve defined your ideal role. You’ve articulated your positioning. You’ve seen patterns in your past work that give you forward momentum.
Now you’ll structure all of it into a system that does the heavy lifting.
This is your Career GTM Engine - and it lives entirely inside your Claude or GPT Project.
Core Components of Your System
These are the living assets you’ll now create, store, and evolve inside the Project:
Positioning Summary
A one-sentence articulation of what you do and why it matters. Built to lead LinkedIn bios, cold messages, and intros.Role Spec
A short-form version of your ideal role: structure, responsibilities, metrics, ideal manager, culture traits, and lifestyle parameters.Story Block
A clear, short narrative about your journey: what you’ve done, why you’re in this moment, and what kind of value you’re focused on delivering next.LinkedIn Rewrite
A full refresh that incorporates your real voice and new direction. GPT will draft this for you from what it already knows in the Project.Referral Templates
Short messages others can use to introduce you to hiring managers, partners, or team leads. You’ll make it easy for people to forward you.Outbound Messaging Drafts
A few versions of your cold outreach—one for full-time, one for fractional, one for strategic explorations. Each one tuned to different archetypes of companies.Target Company CRM
A running list of companies that match your inflection point filter (covered in Section 6). This can live in Notion, Airtable, or Clay, and your Project will help generate research on each.Weekly Reflection Template
A short weekly input where you track learnings, themes, and responses from the field. Helps GPT improve your messaging over time.
How to Build This Inside AI
Use simple structured prompts:
“Draft a LinkedIn summary that reflects my ideal role and matches my tone.”
“Write a cold outreach email to a VP of Ops at a growth-stage SaaS company.”
“Create a referral email someone could send on my behalf to a startup CEO.”
“Summarize the key value I bring to a company going through a post-Series A scale phase.”
“Generate 10 companies to research based on this role spec and the industries I’m aligned with.”
Update and refine these artifacts as your clarity deepens.
Each one becomes a plug-and-play component in your outbound and inbound engine.
Each one reduces friction.
Each one builds surface area for opportunity.
You’re not just preparing to search.
You’re designing a GTM motion that will continue running in the background as you have conversations, learn from signals, and develop new interest areas.
Your next move: scale it with tools.
Section 5: Learn AI by Using It to Scale You
You’re already using AI.
Now you’ll start operating with it—building workflows, automating friction, and teaching it to act like an extension of your process.
This is where your AI Project shifts from workspace to system.
You’ll Learn AI Through Applied Use
You don’t need to take a course or study prompt theory.
You’ll learn AI by doing the exact things your search needs:
Writing 10x faster with consistent tone
Researching company signals across news, funding, and hiring
Generating personalized outreach with minimal lift
Matching your skills to job specs at scale
Drafting comparison docs, one-pagers, and interview prep in your voice
This is applied learning.
And because it lives inside your GTM system, every output is relevant, usable, and cumulative.
What Tools You’ll Touch (And Why)
Start with the essentials:
GPT-4 (ChatGPT Pro) or Claude Opus
Use these for deep project context, system building, tone alignment, and long-form writing. They’ll power your main project workspace.Notion AI
Great for drafting, tracking, and summarizing ongoing job pipelines, ideas, and reflections. Use this to house your CRM and content system if you want it in one place.Clay
Pull company signals, enrich people data, and trigger email workflows. Clay helps you monitor when to reach out and what to say.Zapier or Make
Connect tools you already use—Gmail, Airtable, LinkedIn, calendar—to automate repetitive tasks like saving job leads, logging follow-ups, or sending nudges.Airtable
A simple, visual CRM to track your outreach by company, stage, and point of contact. Easy to search, sort, and scale.Bardeen
Automate lead scraping, news monitoring, or recruiting signals right from your browser. Perfect for passive discovery.Instantly, Smartlead, or Apollo
Run light, automated outbound campaigns to selected audiences. You’ll still lead with warmth, but these tools give you coverage.
Use one or two of these at first. Then expand. You’re layering, not rushing.
How to Structure the Work
Keep your AI Project open every day
Ask it to re-draft, refine, or summarize real things you’re working on
Add new insights weekly: calls you’ve had, learnings from outreach, new positioning ideas
Let the model deepen with you—it remembers what you teach it
This isn’t extra work.
This is the work.
And every prompt you run makes your search stronger, faster, and more creative.
You’ll start noticing a shift: instead of catching up with AI, you’re operating inside it.
And the same way you’ve scaled systems before—now you’re scaling yourself.
Part 6: Spot Companies in Motion Before They Post Roles
Most roles are already filled before they’re ever posted.
The companies you’re built to help are often deep in transition—right before they realize they need someone like you.
This is the moment you’re aiming to meet.
Your system now shifts from self-definition to external awareness.
You’re building pull by spotting motion.
Look for Inflection Points
You’re not just targeting industries. You’re listening for signals.
These are the moments where your background, systems thinking, or leadership make you highly valuable:
A new round of funding
A Series A company prepping for scale
A post-acquisition integration
A strategic shift toward AI or automation
A new C-suite hire reshaping the org
A job post that’s been live for 60 days without a hire
A public layoff that precedes a re-org
Each of these moments creates friction.
And you’ve spent your career solving friction.
The key is to surface these signals consistently—and connect them to companies that match your ideal role spec.
Tools That Surface These Signals
You’ll layer tools into your workflow that make listening easier:
Clay
Monitor companies by funding, headcount change, AI mention, or title churn. Push updates into your CRM or email when something triggers.SignalRank
Prioritized rankings of emerging startups based on funding activity and market indicators. Good for identifying top-performing Series A–C companies.Crunchbase Pro
Filter by last raise date, team size, job openings, or hiring signals.Google Alerts
Track news around target companies, funding rounds, or exec changes.LinkedIn + X (formerly Twitter)
Follow key operators, founders, and vertical-specific newsletters to hear what’s happening before the press release.Bardeen
Automate scraping of team pages, blog updates, or new product announcements.Notion or Airtable (Your Company CRM)
Store every target company and include fields like:Trigger event (e.g., Series B raised)
Key team contacts
Current open roles
Industry alignment
Outreach status
Personalized notes from GPT
Your AI Project stays central to this system.
You can ask:
“Which of these companies seem most aligned to my background?”
“Draft a short context paragraph for each of these five based on recent activity.”
“Summarize what this leadership change might imply for their product org.”
AI handles the synthesis. You show up ready.
Make the Discovery Loop Part of Your Workflow
Set a 30-minute research session each week.
Refresh your CRM
Tag new leads
Log high-signal events
Identify three companies to reach out to
Let GPT help draft the messages
When you monitor motion, you arrive ahead of need.
You’re no longer applying after the fact.
You’re stepping into the story before it’s written.
Part 7: Reach Out with Precision and Warmth
Your GTM system is now live.
You’ve defined your role, clarified your value, built your message blocks, and identified companies in motion.
Now you turn signal into connection.
Warm, smart outbound is how you activate opportunity.
It’s not about mass emails. It’s about context, timing, and clarity.
Start From Your Project Workspace
You’ve already built everything you need:
A clear one-liner that describes what you do
A short, thoughtful paragraph about your recent work
A few tailored messages for different audience types
A CRM of companies in transition
A set of referral emails others can forward on your behalf
Everything lives in your Claude or GPT project.
You can now prompt:
“Write a warm outreach message to the VP of Product at [company], based on their new Series B and my background.”
“Draft a follow-up to this cold email with a link to my case study and a short personal note.”
“Summarize my alignment with this job post using my project context and role spec.”
Each message is personal. Each message reflects readiness.
Where and How to Send
There are two core tracks: direct connection and warm referral.
1. Direct Connection via Email or LinkedIn
Use the tools below to keep it clean and trackable:
Clay – for enriched profiles and email sequences
Apollo or Instantly – for lightly automated, high-relevance campaigns
Smartlead – for sequencing and reply detection with inbox rotation
LinkedIn Messaging – still effective when short and personalized
Keep your cadence intentional:
Day 1: Send short intro
Day 4: Follow-up with 1-line nudge and a clear ask
Day 8: Share a short insight or value add (example: “Just built this AI workflow for a similar company—happy to walk you through it.”)
Track every step in your CRM.
Let GPT draft each variation and log it back into the Project.
2. Warm Referral from a Connector
Use the done-for-you approach:
Draft a full email someone can forward
Attach a short one-pager or case study
Offer a specific conversation ask: 15-minute intro, insight exchange, or interview interest
Keep it light, not salesy
Prompt GPT to write:
“A referral message that explains my AI PM background and how I can help Series A–C product teams navigate automation.”
“A message for someone introducing me to a Head of Ops at a fintech company going through re-org.”
Referrals land because they reduce decision friction.
You’ve already written the brief.
Maintain Consistency With Light Automation
Once you’ve sent 10–15 messages by hand and refined your tone, you can scale it slightly:
Group similar targets by theme (e.g., Fintech, Series A, Ops-focused)
Use Smartlead or Instantly to send 30–50 messages per week
Personalize the first sentence with AI
Build GPT templates for replies, follow-ups, and nudges
Let your system run quietly in the background.
Every week:
Send 5–10 personalized messages
Follow up on past outreach
Log learnings into your Project
Add new companies to your CRM
Outbound becomes motion.
Motion builds surface area.
Surface area creates optionality.
Part 8: Choose from a Place of Strength
You’ve put your system in motion.
You’ve clarified what you want, connected with the right people, and activated real conversations. Some will convert quickly. Some will take time. A few will open doors you didn’t know existed.
This is where your advantage compounds.
Your Engine Keeps Running
You no longer need to pause your life to job hunt.
Your outbound system continues:
Tracking company motion
Refreshing lists
Personalizing messages
Following up on leads
Generating introductions
AI is now part of your operating rhythm.
You’ve taught it your voice, your value, and your intent. Every time you drop a new opportunity into the system, it helps you evaluate, respond, and stay consistent.
You’ve created leverage—the kind that frees you from one-size-fits-all timelines.
What to Say Yes To
Your GTM engine brings opportunities. But your clarity determines direction.
Here are ways to evaluate offers:
Role fit: Does the scope match the work you enjoy and the outcomes you create?
Lifestyle alignment: Does the structure respect your energy, family, and focus?
Growth curve: Can you evolve inside this environment—or will you be parked?
Culture chemistry: Can you show up as you are—and get better at what you’re great at?
Long-term leverage: Will this experience compound into new relationships, capital, insight, or momentum?
You're not choosing between full-time, fractional, or independent.
You're choosing based on clarity, optionality, and alignment.
Let the System Support Transitions
Some people land roles.
Some build advisory relationships.
Some take fractional contracts that evolve into something else.
Some start ventures slowly—on the side, with intention.
Your system supports all of it:
Add new projects to your workspace
Shift your outbound focus toward warm intros or strategic partnerships
Use your AI Project to scope new products, advisory decks, or service design
Keep weekly reflections going—feeding the loop with real-world signal
This isn’t just a job search engine.
It’s a career operating model.
Built by you.
Run by you.
Designed to grow with you.
You’ve already stepped off the default path.
Now you’re building one that holds.
One with structure.
One with momentum.
One with choice.
You’re not starting over.
You’re building forward.
Or pass along the first prompt:
“Create a Claude or GPT project called ‘Career GTM.’ Upload your resume, LinkedIn, one-pagers, and messages. Then ask: Based on this, what role would I thrive in—and how do I build a system to get there?”
Let them build forward too.
And if you found this personally valuable, would love to have you join so we can share more on engineering your future with intent, purpose and focus.
Subscribe for real systems to navigate your career like a go-to-market motion—whether you’re stepping into your next exec role, exploring fractional work, or building the business only you can lead.
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