Sam Jacobs

Founder & CEO

I build elite, modern GTM operators - CROs, CMOs, CCOs, and Revenue Operations leaders - who drive growth at the world’s fastest-growing B2B companies, including Salesforce, Hubspot, Stripe, Oracle, Snowflake, Clay, Klaviyo, Xero, Upside, Owner.com, Otter.ai, and Square

That’s the mission behind Pavilion, the leading global community of over 10,000 high-performance go-to-market executives. We exist to help ambitious professionals unlock and realize their full potential—not just as employees, but as leaders, thinkers, and builders.  

Pavilion is a paid membership for GTM leaders at every level. We provide tactical support, advanced education - incorporating financial literacy, advanced AI-powered GTM motions, and modern leadership tools - career acceleration, and a powerful peer network to help Members perform better in their roles and grow into the next. We operate in every major global hub and represent a new way of thinking about career development—community-powered, principle-led, and relentlessly practical.

This all started with a belief: that greatness exists within all of us. Sometimes it just needs the right mechanism to bring it forth.

To learn more, visit: www.joinpavilion.com

I also co-host the Topline Podcast with AJ Bruno and Asad Zaman.

And I wrote a bestselling book, Kind Folks Finish First, about building with kindness at the center.

Host, Sales Hacker Podcast

Host of The Sales Hacker Podcast featuring interviews and discussion with leading sales practitioners from high growth companies around the world.  

Learn more here: https://www.saleshacker.com/podcast-announcement/

Dear CEOs, Investors, Boards,

Take some time to understand the discipline of marketing.  

It's clear we're approaching 2026 and most of us are right where we were 15 years ago.  In fact, it might be worse.

15 years ago people had a deeper appreciation for brand.

Now, if people think about marketing at all, it's exclusively demand generation.  

SOME STORIES FROM MY COACHING CALLS

I've been doing 4-5 calls with Pavilion Members a day for the past few weeks as we near the holidays.  The goal is to help as many people as possible during what can be a high anxiety time.  

Negotiating EOY comp.  Getting fired.  Maneuvering for a promotion.  Taking on responsibilities of a recently fired exec.

What's become clear: marketing is under siege.

Some anecdotes:

- A job interview for a CMO that has a screening question blindly asking "How many MQLs did you generate last quarter?" with no additional context (!!??)

- CMOs being fired and all of marketing rerouted to the CRO with no CMO backfill

- Continued attacks on any budget line item not directly tied to hiring more reps or near term demand gen

- CMOs & marketing dept. being fired after crushing every number because the company needs to show improved profitability before an exit

The list goes on and on.

The #1 feeling most marketers are expressing right now: EXHAUSTION

BACK TO THE OPEN LETTER

So if you're a CEO or Founder or Investor reading this, a couple things:

1. Brand is long term demand generation.  If you want to drive revenue in 2026 and 2027 and 2028 and 2029 and onward you'll need a brand.  Some part of your marketing budget should be allocated towards it.

2. You don't need a "Chief Storyteller".  That's your head of Marketing.  You need a marketing department.  Stop being a moron.  Just hire a great marketer.  

3. We are in a world of commodity software products where people think they can vibe code what you've spent 10 years building in 30 minutes on the weekend.  You'll need marketing to differentiate yourself.  Your marketing can't just be "Ha ha they don't have any security and we're SOC-2"  

4. Your CHEAPEST path to demand generation is MARKETING.  Not tons of sales people.  You don't need more AEs.  You need program spend that puts  your story in front of as many people as possible.  That generates awareness and interest and your sales team converts that to revenue.  

5. You're in the business of driving efficient revenue growth.  That comes through MARKETING and, relatedly, through PARTNERSHIPS.  Hiring 50 SDRs with a 3 person marketing team isn't smart.  You look like a fool.  INVEST in the discipline of marketing.

BOTTOM LINE

I am having call after call with Pavilion Members tearing their hair out that you have no f-ing clue what you're talking about when it comes to marketing.

Take some courses through Pavilion if you need to or DM me.  

But you're doing it wrong and it's going to cost you results in 2026.

Thanks for reading.

Love,
Sam

CEO @ Pavilion | Co-Host of Topline Podcast | WSJ Best Selling Author of "Kind Folks Finish First"

In 2026, the race will split into two categories.  

VC Backed AI Native:
- Expected hyper growth.  Growth ain't a goal.  It's a commandment.
- Experimental ARR facing GRR collapse.  Explosive on a chart.  Fragile IRL.
- Gross margins that are “fine for now” and hand-waved away as a future problem.
- Dependent on hype cycle and enterprise enthusiasm
- Small chance at $1B ARR
- Race to get to exit or secondary before you have to prove the business model
- VC investors whipping you into a frenzy 
- "Unicorns are dead.  I'm all in on SuperNovas (or a new moniker my team came up with last night)
- Brutal intensity but maybe you'll end up like Fyxer, Manus, Elyse, Lovable and get to the finish line
- Expected ARR Growth: 
-- 0-$100M - 300%
-- $100M+ - 200%
- Time Horizon: Get out ASAP before the music stops
- "This time it's different"

Non-AI SaaS / Everyone Else (including me):
- Growth that’s intentional, modeled, and meant to survive contact with reality
- ARR that compounds quietly, supported by actual customers and real CS motion
- Goal is Rule of 40-60
- Gross margins you can explain without squinting (65–90% and proud of it)
- Iced out of the hype cycle
- No meaningful chance at $1B ARR
- Long term focus
- "Long term games with long term partners"
- Slow and steady wins this particular race (which isn't the same race the AI teams are running)
- Expected ARR Growth:
-- 0-$100M - 40%
-- $100M+ - 20%
- Time Horizon: 10+ years
- "I'll just keep building a good business. (And sleep at night)"

If you're in the first category, enjoy the ride.  It might burn you out.  But you also might win.  

If you're in the second category, find your composure and design your business around steady compounding every day.

Personally, I'm in the second category.

Community is the antithesis of AI native.  

It's real relationships
Real people.
And real experiences.

It doesn't respond well to hyper growth pressure (and often breaks when forced).

It does respond well to a long term steady vision, a focus on human connection and meaning, and an emphasis on craft.  

There's no judgement.  

We all have to grow where we're planted.

And mine is one that builds over years and decades vs quarters.  

What game are you going to play this year?

There's >$10B of ARR in this picture.  

And even with operators of this size and scale, folks need support.

We just got back from a 3 day Pavilion Gold Winter Retreat in Mexico, the first of its kind for this program.

To say it was "magical" is an understatement.

Something happens when you get people away from their screens and their Zooms and put them in a beautiful spot together to share, to experience the beauty of the environment, and to workshop difficult problems.

This group brought their full selves to this experience.

Discussions about:

Being laid off.
Negotiating the right package to protect yourself and your family.
The existential fear of not moving fast enough in a world dominated by AI.
What great operators are doing to stay ahead of the curve.
How to solve backwards from enterprise value.
Creating long-term incentives for your management team to drive business outcomes.
The POV of LPs who haven't received a distribution check in years from your 2021+ fund vintages.
Chips in shoulders translating to chips in pockets.
The profile of great founders.
Seat-based pricing migrations to usage-based pricing.
Dealing with difficult boards.
Sharing perspectives across PE, VC, and operators.
Building a career that spans operating roles, board roles, advisory roles, and asset allocation.

Beyond that though, and because we all knew that Chatham House Rules prevailed, people truly opened up.  

They shared their challenges.
Their fears.
Their concerns.

GTM can be a grind.
At any altitude.  

Even the folks that seem like they have it all are working their way through their careers with fear, anxiety, and optimism all at once.

---

Within Pavilion Gold, we do dinners, we do virtual masterminds, we connect people to subject matter experts to answer difficult challenges.

We put people into non-competitive peer groups called Small Councils where you can learn from a group of operators who become friends and ultimately your personal board of advisors.

And all of that is awesome.

But IRL is where the real magic happens.

And I can tell you -- it's powerful.

Real life.  
Real human connection.

That's the best hedge against a world dominated by AI.

---

We're going to do 2 big retreats a year plus a dedicated track at GTM (our big conference) for Gold Members.

Next up is Jackson Hole, June 9-12.
Next year we're looking at Whistler in Feb of 27 and then Amelia Island in June of 27.  
TBD on 2028 but we'll probably try to do something in Europe.

---

If you're an operator at scale and any of this sounds interesting, DM me.

There's no online sign-up to be clear.

I personally interview every Member.

We're not "scaling" Pavilion Gold.

It is an elite membership.
It's not for everyone.
It's a meaningful investment.

But it will change your career and your life.

So there's that.

The beginnings of a whirlwind tour that will take me through Washington DC, Mexico, Miami, Boston, Vegas and New York. 

First stop: Frankfurt where I’ve been waylaid due to terrible weather in Europe. 

Had to find a sports bar to watch the NFL playoffs. 

An attempt to stretch my legs took me through some kind of Red Light district by the train station.  Will find a different route back to the hotel. 

Over the next two weeks:

- Pavilion Gold Winter Retreat in Mexico featuring a number of incredible operators and investors including Cassie Young, Nate Nasralla, Jonathan Moss, Monika Saha, 🌱 Allison Munro, and many more. 

- Miami to meet with Mike Lovell and brainstorm on the Miami Chapter

- Boston for a team offsite with Rich Gardner, Julia Segel, Josh Mait, Nicholas Tarnoff, and Samantha Carducci  and a big all community town hall to announce some major updates to the Pavilion community 

- Vegas to speak at the AlphaSense SKO with Kiva Kolstein, Ashley Hansen Grech, and Steve Rowland  

- Then back to Spain via NYC

Gonna be a whirlwind. 

Follow along. 

For now:

Frankfurt you have not made the best first impression and, on behalf of Carly Pallis, 

GO BILLS

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Someting beautiful and special about being at the airport at 6am in the cold winter morning, the sunrise barely scratching its auburn hues against the horizon, watching people get dropped off on their way to their flight.

Hugs.  Kisses.  And echoes of "love you" throughout the terminal as people say goodbye on their way to some new adventure. 

Sometimes the sheer overwhelming joy of being alive and giving and receiving love can catch you by surprise.

It's good to be alive.

After 25 years of building and scaling revenue teams across >$500M in ARR, the #1 reason I see sellers, managers, and CROs fail isn’t effort, strategy, or hustle.  It’s a lack of basic financial acumen (and I know Gal Aga agrees with me).

If I were going to design a course to fix that problem for revenue leaders, here’s exactly how I’d structure it. 👇🏻

Module 1: Understanding the P&L and the core financial statements

This module would cover financial literacy, not accounting theory.  The goal wouldn't be to go deep on the different kinds of depreciation or why R&D should be capitalized.  

It would be to quickly help revenue leaders get up to speed.  

Specific elements should include:

- How the P&L actually works: revenue, gross margin, operating expenses, EBITDA
- How the P&L connects to the balance sheet and cash flow statement
- Where revenue decisions quietly create downstream cost, margin, and cash consequences
- What “healthy” vs “fragile” P&Ls look like at different stages of growth

Key Takeaways:

Leaders would be able to scan a P&L in 60 seconds and understand:
- How the business is really performing
- Where the obvious gaps and inefficiencies are
- Whether growth is creating leverage or just hiding problems

Module 2: Unit economics and the true cost of growth

This is where most revenue leaders get dangerous with partial knowledge.

We would cover:
- GRR, NRR, churn, expansion, and why revenue quality matters more than topline growth
- LTV:CAC and why averages lie
- Cohort and channel-based unit economics
- How sales efficiency, payback periods, and growth rates interact

Key Takeaways:

You'd know whether growth is creating value or destroying it — and which segments, channels, or motions are responsible.

Module 3: Valuation, benchmarking, and building durable value

Benchmarks without context are how bad decisions get justified.  Too many people have no clue why revenue multiples exist, what they imply, and why they change with the market.

Benchmarks are the crutch of the half-informed.  This module would change that.

We'd focus on:

- How investors actually think about valuation
- Why different business models earn different multiples
- The real drivers of revenue and EBITDA multiples
- A valuation-first mindset for revenue strategy and investment decisions

Key Takeaways:

You’ll stop optimizing for vanity metrics and start making decisions that compound long-term enterprise value.

Revenue leadership without financial fluency is guesswork with confidence.

This course would be designed to change that.

Given its importance, I'm hoping someone is building this course and target it at CROs, CMOs, and revenue leadership.  

And given its urgency, I would hope that someone would launch this course on January 27th, ideally to the best and most enduring revenue community in the world.

Because this course would be an absolute banger.

Fingers crossed.

🤞🏼

Two important and related books. 

Wallace Wattles “The Science of Getting Rich” and

James Carse “Finite and Infinite Games”

Wattles speaks of the difference between the Creative and Competitive Minds. 

Carse classifies two types of games. Finite games are played for the purpose of winning. Infinite games are played for the purpose of continuing the play. 

Connecting those dots: there is a different approach to life that is not defined by the success or failures of other people but simply by your ability to continue to create from the source of your personal genius.  

Forcing myself to play other people’s finite games has been the source of most of my unhappiness in life. 

And conversely, the freedom to pursue creative non-zero infinite games has been the source of my greatest joy.

A mentor once told me, "At some point everyone becomes a capital allocator."

MY INTERPRETATION:

There's only so far advisory or employee equity will take you.

If you want to be a player in this world you'll have to write big checks.  

Like it or hate it, the way power is distributed is according to who actually invests.  

Not advisory equity.
Not small $5K checks.

But the people that commit 6, 7, and 8 figures into causes and companies they believe in.

Many people are understandably not in that position.
Many people don't have the privilege of coming from that position,.
Many people are struggling every day to simply put food on the table.

This is not a judgement.
At many times in my life, I've been one of those people.
For the majority in fact.

So this is not social commentary.

But there are lots of people who could make meaningful commitments, who have simply become used to people giving them ownership without making a financial contribution for it.

And those folks will always be on the outside.

If you want to be on the inside:

Your goal should be to create enough resources that you can make meaningful bets on the things you believe in.  

Only if you want to be on the inside.

And everyone's journey is their own.

But the path to power is derived from capital allocation.

So you have to get out your checkbook.

In my early 20's, I moved into a homeless shelter.

It wasn't because I fell into financial hardship, but rather I wanted to experience what service oriented work could look like outside of traditional ministry vocation. (Hello Bible college degree 👋)

This experience led me to non-profit work. It was my first introduction into how business practices and redemptive vision could co-exist...and I was hooked! 

After six years in the non-profit sector I found myself hosting conversations with leaders around the globe through a bi-weekly podcast on redemptive entrepreneurship and impact within culture. With over 200 interviews with leaders across the world, we grew this message of Gospel Driven entrepreneurship to an audience of 10,000 downloads a month.

This passion project led me to joining two amazing teams with the world's #1 leadership expert, John C. Maxwell and eventually the nation's #1 financial expert, Dave Ramsey.

Serving in a variety of roles over the years, I've found a niche in helping redemptive leaders accomplish large visions through helpful digital strategies, carving a passion in go-to-market campaigns and customer journey optimization.

I've come to believe (as Andy Crouch has said) that today's digital assets are tomorrow's cultural artifacts. We build digitally because we believe something about the world, something about how the world is today and what it should be tomorrow.

P.J. Simmons

As we enter into 2026, I’m stepping into a new role as Head of New Business for Whiteboard. Over the last 4 years, I’ve sat with a myriad of clients who are working to solve problems that drive meaningful outcomes for their business. 

These problems range from:
- Identification of market opportunity for new product launches
- Positioning and messaging for brand transformations
- Go-to-Market clarity and plans in new technology environments 
- Creating intuitive UX experiences for content first organizations
- Donor formation campaigns for attracting younger demographics 
- Empowering internal marketers and web teams with low-code technology 
- Lead acquisition challenges to ensure acquisition costs are ROI+
- Providing consultation on agentic engine optimization strategies 
- Many, many more.

Because no problem is alike, I’ve found myself developing somewhat of a muscle for pattern recognition:

Challenge -> Opportunity -> Unique Contribution -> Differentiation -> Strategy -> Execution

In seeing these patterns, I’ve really come to enjoy the process of aligning our services at Whiteboard to meet the needs of our clients - based on the outcomes that matter most to their business, not just the deliverables requested at face value.

It’s been advisory - strategy - planning - service based execution.

Because of this, I’ve now been asked to lead and steward Whiteboard’s process of developing new business. 

And I am ecstatic.

I’m ecstatic to serve, to advise, and ensure that when an organization is in need, we’re aligning our services to outcomes that matter most to them.

So - here’s what we have going on…

Whiteboard provides strategic advisory and creative execution in brand, web, and marketing campaigns.

Our desire is to be the leading creative and technology partner to visionary leaders and brands.

Simply put - we make vision, visible.

I’ll drop a comment with a link to our capabilities deck.

And if there’s a need in 2026 for you, it would be an honor for me to advise on how we can serve.

My DMs are open.

I didn’t expect to be here

But here we are…

Nearing 40…

Wearing blue jeans with Brooks tennis shoes and socks with my kids faces on them. 

But I’m embracing it.

The Ministry of Imagination

What happens when Whiteboard begins to partner with some of the world's most talented creative agencies in their own right?

You get a creative collective founded on the belief that imagination is responsibility - forging hopeful and redemptive futures together.

I'm excited to announce our most recent partnership with Colours and Shapes as we've respectively created physical and digital environments for brands like:

- TED
- Ford
- Practicing the Way
- Passion
- NCR
- Clear
- IEX
- More

We specialize in:

- Brand Strategy
- Environmental & Experiential Design
- Web/UX Design
- Campaigns
- Animation & Motion Design
- More

In an age of overload where noise drowns out meaning and speed overshadows substance, we believe creativity can renew culture, technology, can serve humanity, and collaboration can shape new futures.

Feel free to check out the new initiative here: https://lnkd.in/gXvdJQiQ

Organizations I want to collaborate with in 2026 to provide brand, web, and campaign services to. Obviously we have an existing pipeline at Whiteboard of clients we serve, but these would be a ton of fun:

World Vision
Big Brothers Big Sisters of America
Convoy of Hope
Nike
Human Rights Watch
International Justice Mission
InterVarsity Christian Fellowship/USA
RightNow Media
Special Olympics
YouVersion
The Walt Disney Company
Warby Parker
Center for Humane Technology
Spotify
Basecamp
NPR

I always know I'll run into a friend when visiting Franklin, Tn for a quick trip with a client. 

Great to see Trey Sheneman today and having a quick catch up!

taplio

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The Battle

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