Greg Moran

Multi-Exit Founder & CEO, Advisor, Investor, Board Member | Posting daily insights to help you scale to $100m+. Host - The Founder’s Journey Podcast

Author of The Adaptive Innovator | Creator and Host, Scaling Across Borders | Founder | Investor | Founder Coach

NOTE: IF YOU'RE TRYING TO CONTACT ME, USE GREG@SCALINGACROSSBORDERS.COM, NOT LI MESSAGES. It's unmanageable and I will not respond through LinkedIn messages or InMail.

I’ve been a founder for most of my adult life, from glass-walled boardrooms in New York and Pali Alto to coffee-stained coworking tables in Kosovo and Delhi. Not because I planned it that way, but because I could never quite shake the pull of building something from nothing.

In my early years, I chased growth at all costs. The pace was relentless, the stakes high, and the wins… like realizing a bottled-up vice for the first time. You knew it was staying with you, for better or worse. I built and exited multiple companies, including two at nine-figure valuations.

It looked great on the outside, but inside? I was riding a bull that was kicking my ass.

Building a company is like taking off in a plane you’re still bolting together mid-air. The only goal at first? Get enough distance between you and the ground so when shit goes wrong … and it will … you’ve got time to respond before the ground rushes up to meet you.

If you’re not intentional, that ground gets closer a lot faster than you think.

That realization changed everything.

Today, I’m still building, but on my terms. I help founders scale with freedom: keeping their vision intact, owning their time, and leading teams built on trust and durable systems, not constant fire drills.

I do that through:

-> Evergreen Mountain Equity Partners — investing in and advising values-aligned companies.

-> Outsorcy — an AI-first, decentralized talent platform helping companies scale global teams smarter.

-> Scaling Across Borders — a docuseries capturing the unfiltered stories of entrepreneurs building in overlooked markets worldwide.

-> My book, The Adaptive Innovator — a playbook for leading with clarity and adaptability in an unpredictable world.

I post founder-to-founder insights here daily … from scaling a remote team across time zones to navigating your first big exit … so follow along if you want the real playbook, not the highlight reel.

The world’s best founders aren’t all in Silicon Valley … and I’m here to prove it.

-> More at GregMoran.me

-> Subscribe to my newsletter: Scaling Beyond Borders at https://expert-creator-5823.kit.com/82c0e3e8c9

-> Buy The Adaptive Innovator at https://a.co/d/75ifhwQ

📬 DMs open for 1:1 coaching, retreats, speaking and credible business opportunities.

Chief Executive Officer (Interim)

At Conquer we are making selling smarter through our enterprise sales enablement platform. Our comprehensive solution combines automation, advanced analytics and AI-driven insights to empower sales teams and drive revenue growth. 

By leveraging our platform, sales professionals can optimize their strategies, enhance customer engagement, and close deals more efficiently. 

Helping Executives and Professionals break into Private Equity as Operating Partners, Executives, Board Directors, or PE-Backed Buyers — positions most never knew were accessible to them.

The Real Problem: Most executives are invisible to PE not because they lack credentials, but because they position themselves wrong. They send resumes (job seeker signal) when PE needs Investment Theses (owner signal). They speak corporate language when PE needs value creation metrics.

My Background: Founder & CEO Single Family Office, Independent Board Director on a dozen boards and Chair of the PDA PE Portfolio Company Certification Task Force. Former PE Principal who made the same transition you want. 100+ M&A transactions and raised over $1 billion in capital. I've been the operator PE firms hire, the board director who advises them, and the investor evaluating thousands of deals & candidates. 

What I Do: I know exactly what they want and what works and compress the typical 18-24 month ‘if ever’ DIY struggle into 12 weeks. Executive & Professional strategic refinement of positioning and Introductions, without losing months of 'Opportunities'

•	PE Strategic Positioning 
•	PE-Readiness Assessment & Gap Analysis
•	Investment Thesis Development
•	Impact Story & Portfolio Examples
•	Targeted PE Network Introduction Map
•	Investment Thesis Pitch Event Invitation
•	Direct PE Introduction Events
•	Private Group Community (Peer networking bonus)

Your track record doesn't expire—your market window does. Let's talk about your PE transition.

Greg Head

I spent 25 years watching boards destroy value in a way nobody talks about.

Not through bad deals or weak talent.

Through something quieter: blurred lines between governance and operations.

Here's what it looks like in practice.

A board member with operating chops decides to "help."

They start joining weekly standups.

Request dashboards.

Weigh in on pricing models, sales comp, product roadmaps.

The CEO treats it like guidance.

The team treats it like direction.

Then results miss.

And suddenly?

"I'm just a board member. That was your call."

The hat gets switched retroactively.

Authority flows one way. 

Accountability flows the other.

That's not support. 

That's a shell game.

I've seen this pattern wreck companies from the inside.

Not because anyone was incompetent.

Because the system allowed someone to operate without owning the outcome.

The damage compounds fast.

CEOs second-guess themselves because someone "above" them might reframe the decision later.

Exec teams start optimizing for board perception instead of market reality.

Speed dies. 

Trust evaporates.

You can't build a durable business when authority and accountability live in different zip codes.

The best boards I've worked with don't do this.

They're ruthlessly clear about lanes.

Governance. 
Capital allocation. 
CEO support.

That's it.

If you're going to step into operations, own it.

Define who owns the decision before you influence it.

Stay accountable to the result, not just the recommendation.

If you're advising, advise.

If the CEO ignores you, that's a CEO problem to solve through governance.

Don't create shadow authority through pressure or proximity.

And if you're the CEO?

Name the lanes early.

Be explicit about when you're accepting input versus direction.

Don't let decisions get made implicitly through board dynamics.

You're accountable either way. 

So protect your operating authority like it's oxygen.

Switching hats after the fact doesn't just erode trust.

It collapses the foundation value creation depends on.

Clean roles. 
Clean accountability.

That's how real operators build real businesses.

Helping Professionals break into Private Equity as Operating Partners, Executives, Board Directors, or PE-backed buyer | How to sell your business to PE | Founder Single Family Office | 100+ deals | $1 billion raised

The 5 metrics Private Equity cares about.

Everything else is noise.

PE firms don't build dashboards to feel informed. 

They build dashboards to make decisions.

The only 5 KPIs that matter to PR:

1.  Customer Acquisition Cost tells you if growth is sustainable or just expensive. Most operators can't answer this in 60 seconds.

2.  Lifetime Value shows if customers are assets or liabilities. You need 3:1 minimum against CAC. Anything less? You're subsidizing growth.

3.  Net Revenue Retention reveals if you're building or churning. When existing customers expand their spend, you've got a compounding business. When they leave, you're trying to fill a leaky bucket.

4.  Gross Margin exposes unit economics. SaaS under 70%? Services under 40? You don't have leverage. You have a job that scales linearly.

5.  Cash Conversion Cycle shows if you're profitable or just pretending. Revenue on the P&L means nothing when cash never hits the account.

Five metrics. Five decisions. Every week.

I've walked away from deals where revenue looked great. 

But, these five numbers told the real story.

Here's what nobody tells you about landing a job at a PE-backed company.

The playbook everyone follows is backwards.

They chase:
• McKinsey on their resume
• "PE experience" bullet points
• Perfect LinkedIn keywords

Wrong game entirely.

PE-backed companies operate on a different clock.

They've got 3-7 years to multiply value and exit.

Every hire either accelerates that or slows it down.

So they're not hiring credentials.

They're hiring velocity.

The real question they're asking:

"Can this person make us more valuable faster?"

That's it.

Here's what moves the needle in their world:
~Revenue growth that compounds
~Margin expansion that sticks
~Systems that don't break when you scale
~Execution without constant oversight

If your track record doesn't answer "yes" to those, you're invisible.

The roles that get hired fastest:
• Finance leaders who speak EBITDA
• AI and automation implementers
• RevOps and supply chain fixers
• Sales leaders who've scaled before
• Product people who ship fast
• Anyone who builds reporting systems

These aren't random.

They're the levers that change enterprise value.

Frame your experience like a deal memo:
- Show the before and after.
- Quantify what shifted because of you.
- Prove you've operated under pressure.

Most people waste time here:

Cold emailing the PE fund directly.

Better move:

Go straight to the portfolio companies.

1. Find the CFOs.
2. The Operating Partners.
3. The talent acquisition teams.
4. Execs who've already taken companies through exit.

They're the ones actually hiring.

When you interview, skip the corporate theatre.

They don't want to hear about your "passion for the mission."

They want to know:

Have you fixed broken things?

Can you prioritize when everything's on fire?

Do you need your hand held?

Fastest way in:
~Join a smaller PE-backed company first.
~Work for a firm that services portfolio companies.
~Sell into PE-backed businesses.

Once you're in the ecosystem, doors open fast.

The pattern recognition becomes your currency.

It’s been a while since I started my role at PE-Ready Executive Accelerator - The Greg Head Helping Executives & Professional Break into Private Equity, but I wanted to share this update with everyone.

I watched another executive get cut last month.

Three months in. 
Strong resume. 
Good intentions.

Gone.

The pattern is always the same.

PE-backed companies don't give you time to figure it out.

Here's what actually gets you fired:

You mistake activity for impact.

Being busy means nothing if you're not moving the needle.

You chase the wrong fires.

Treating symptoms while the real value leaks go untouched.

You wait for perfect information.

PE values decisive judgment over endless analysis.

You create dependency.

When every decision needs your approval, you become the problem.

You hide problems until they explode.

Delivering bad news late destroys trust instantly.

The real issue isn't making mistakes.

It's creating uncertainty.

PE firms can handle problems.

They can't handle surprises.

Most executives think they have quarters to prove themselves.

They have weeks.

The ones who survive understand this from day one.

The Mistakes That Get PE-Backed Hires Fired Fast.

Most PE-backed hires don’t fail slowly.

They fail suddenly.

The One Question Private Equity Is Always Asking About You

But doesn’t ask out loud.

But it drives every decision:

“Does this person act and reduce risk — or create it?”

Not your resume. 

Not your pedigree.

They're measuring: Do you shrink problems or multiply them?

Every move you make answers that question.

The way you frame bad news.

The speed you kill small fires.

The clarity you bring to chaos.

The systems you build so things don't break twice.

Most people think PE firms are hunting for the smartest person in the room.

They're not.

They're hunting for the person who makes everything easier.

The executive who simplifies complexity instead of adding layers.

The operator who surfaces invisible work before it becomes a crisis.

The leader who turns one-time wins into repeatable systems.

That's the actual game.

You're not proving you're smart.

You're proving you're safe.

And in PE, safe means scalable.

Think about it like this:

When something breaks, do people come to you because you'll fix it fast?

When you deliver bad news, does leadership breathe easier or brace for impact?

When you build something, does it work without you or fall apart the moment you're gone?

The executives who understand this build trust at 10x speed.

The ones who don't spend their careers explaining why things went sideways.

If a PE firm shadowed you for a week, would they see someone who shrinks problems or multiplies them?

How I Used AI to Find $500K+ in Hidden Cash Flow That PE Spreadsheet Didn't (Without Cutting Headcount)

Every business has a leaky bucket.

Most operators panic and start cutting headcount.

That's the wrong move.

I run AI analysis on three specific areas first:

1.  Leads die in the inbox.
2.  Reps stop following up.
3. Existing customers churn quietly.

Problem: Sales reps take too long to respond to new inquiries.

AI Solution: AI chatbots or agents engage leads in seconds. These tools qualify prospects and book meetings on the calendar immediately.

Problem: Most sales require five or more touchpoints, but reps quit after two.

AI Solution: AI sequences send personalized follow-up emails based on specific prospect actions. The AI varies the messaging and timing to stay relevant without human effort.

Problem: Companies focus on new sales while current clients leave due to neglect.

AI Solution: AI sentiment analysis monitors support tickets and usage data. It alerts the team when a customer shows signs of frustration so a human can intervene before the account cancels.

We didn't fire anyone.

We didn't renegotiate contracts.

We fixed the leaky bucket

You don’t fix a leaky bucket by pouring more water in it.

Stop climbing the corporate ladder.

Buy the company instead.

You spend years building someone else's business.

You grow your division. 

You hit your numbers.

Your reward is a bigger title and a bonus...maybe

The owners get the equity value.

You think you need millions to buy a business.

You don't.

Your track record is the currency.

Private equity firms have capital.

They need proven operators to run their companies.

This is the Executive-as-Acquirer model.

They provide the money.

You provide the playbook.

You become CEO with a major equity stake.

I watched a division President do this.

She ran a $200M unit for a public company.

She partnered with a PE firm.

They bought a $40M competitor.

Three years later, they sold it for $120M.

Her personal take exceeded $10M.

PE firms want executives with:

→ A history of full P&L ownership.
→ A specific, repeatable growth playbook.
→ Deep expertise in a single industry.
→ A clear thesis on how to create value.

Here are your first steps:

→ Define your ideal acquisition criteria.
→ Document your 100-day plan and value creation strategy.
→ Identify PE funds that invest in your sector.
→ Build relationships with deal sources.

Your salary pays your mortgage.

Your equity builds generational wealth.

Stop renting out your talent.

Start deploying it for ownership.

You are the asset the capital is searching for.

I help Professionals break into Private Equity as Operating Partners, Executives, Board Directors, or PE-backed buyer | How to sell your business to PE | Founder Single Family Office | 100+ deals | $1 billion raised

I've watched 47 Investment Bank Analysts get rejected by Private Equity this year who would've been automatic hires 18 months ago.

Same pedigree. 

Same modeling chops. 

Same work ethic.

What changed?

The skillset that made you valuable in 2023 became table stakes in 2024.

I've been on both sides of the M&A table for 25 years. 

Run businesses...bought them...Fixed the broken parts...and then sold them. 

Raised over $1 billion across portfolio companies.

Those landing offers today bring two capabilities that weren't on anyone's radar two years ago.

Capability 1: Operational Risk Assessment

This isn't about satisfying LP questionnaires.

It's about identifying cash flow vulnerabilities before the deal closes.

How does a 40% turnover rate in diverse talent pools compress exit multiples?

They model the downside, not just check compliance boxes.

Capability 2: AI as a Value Creation Accelerator

PE firms aren't hunting for AI companies.

They're acquiring underperforming operations and using AI to compress turnaround timelines.

Here's what this looks like in practice:

A portfolio company has a bloated sales process with 47% of rep time spent on admin work. 

You identify where an AI agent can automate CRM updates, proposal generation, and follow-up sequences. 

That 47% becomes 12%. 

Sales capacity doubles without hiring.

Or you inherit a customer service operation drowning in tickets. 

You implement an AI triage system that resolves 60% of inquiries without human touch. 

Response time drops from 18 hours to 90 minutes. 

Churn falls by 8 points.

I've spent two decades fixing leaky sales funnels and systematizing chaos. 

The difference now isn't the problems. 

It's the speed of the fix.

AI compresses "eventually profitable" into "profitable next quarter." 

Analysts who can identify these leverage points become operators, not just spreadsheet builders.

What This Means for Your Career

Your MBA and financial modeling foundation remain essential.

But they're no longer differentiators.

The analysts who can't articulate how ESG affects cash flow or where AI creates operational leverage are competing with yesterday's playbook in tomorrow's market.

If you want to break into PE today, you need to think like an operator who sees risk and opportunity beyond the model. 

That's the shift.

Your LinkedIn profile is your most underrated tool for breaking into private equity.

You think PE opportunities come from your network. 

Or a headhunter.

You believe it's about who you know.

This is outdated thinking.

Private equity firms need deep niche expertise.

They need operators who see around corners.

When they look for this expertise, they don't start with their phonebook.

They start with a search bar.

A fund wants to buy a SaaS company in the construction space.

They need to vet the tech. 

They need to understand the customer.

They search LinkedIn for "construction tech trends".

They find you.

You have been writing about this exact topic for six months.

Your posts are sharp and specific.

You offer a clear point of view.

You get a message. 

Not from HR. From a partner.

The first project is a diligence assignment.

The next is an offer for a board seat.

Your content becomes your digital resume.

It works for you while you sleep.

It qualifies opportunities for you.

This is not about vanity metrics. 

It is about proving your expertise.

→ Your analysis of a recent deal in your sector.
→ A framework for operational improvements you've used.
→ A prediction about a market shift no one is seeing.
→ Your take on new technology affecting your industry.

A resume shows where you have been.

Your content shows how you think.

A PE firm is not buying your past.

They are investing in your future judgment.

Stop treating LinkedIn like a job board.

Treat it like your personal thought leadership platform.

Don't ask for a role.

Demonstrate your value.

The right people will find you.

A PE board seat isn't a corporate board seat. 

It’s an entirely different sport.

Public company boards prioritize governance. 

They manage risk. 

They ensure compliance. 

The timeline is long. 

The pace is measured.

A PE-backed board is about speed. 

The goal is value creation. 

Now. 

Your timeline is compressed to 3-7 years. 

Your singular focus is a high-multiple exit.

The work is different.

Corporate boards meet quarterly to review reports.

PE boards meet constantly to solve problems.

Your role is hands-on. 

You are an operator, not an overseer. 

You have a direct line to the firm’s Operating Partner. 

The 100-day plan is your bible.

What this means in practice:

→ Driving the value creation plan
→ Mentoring the CEO on rapid execution
→ Making introductions to key customers
→ Helping vet acquisition targets
→ Constantly preparing the company for sale

A public board seat is often a capstone to a career.

A PE board seat is a high-stakes sprint. It is not a retirement gig.

Public boards ask: "Are we compliant?"
PE boards ask: "How do we grow faster?"

One role protects existing value.

The other builds new value from the ground up.

Know which game you are signing up for.

Your executive skills are becoming obsolete.

Your job title is safe for now.

Your job description is not.

Soon, 'executive' will mean 'AI-powered executive'.

The two roles will be the same.

This is not about learning to code.

You do not need to be a data scientist.

You need to be the pilot, not the engineer.

The old executive role was managing people.

The new executive role is managing systems of decision.

Most leaders ask their teams for reports.

They get a summary of the past.

AI-powered leaders ask for models.

They get a forecast of the future.

This is the new job description:

→ Ask your data team better questions. 

Not 'What happened?', but 'What is the most valuable question we could answer with our data?'.

→ Identify business processes that run on guesswork. 

Find the points of friction where your team makes slow, gut-feel choices.

→ Deploy AI to automate and improve those specific decisions. 

Start with pricing, inventory, or lead scoring.

→ Build a culture that trusts data. 

Reward teams for making fast, profitable decisions based on the models.

Yesterday's value came from experience and intuition.

Tomorrow's value comes from the speed and accuracy of your decisions.

Your intuition is still critical. 

It helps you ask the right questions.

But you must stop running your business on feelings.

You must start running it on a decision engine you help design.

The best leaders are no longer just leading people.

They are building systems that lead the business to the right answer. 

Faster than the competition.

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The Battle

Greg Moran

Greg Head

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The Battle

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Greg Head's LinkedIn Performance

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