Cosmo Tech | The Decision Twin Platform for Supply Chain, Finance & Asset Leaders at Fortune 500 Scale | Simulate Tomorrow. Decide Today.

I specialize in the messy middle of B2B SaaS scaling—taking companies from erratic growth to a disciplined, high-performance revenue engine.

Most sales teams don’t fail because they lack talent; they fail because of ambiguity.
When forecasts can’t be trusted, pipelines move only through founder heroics, and managers report activity instead of owning outcomes, you don’t need another playbook—you need an operating system.

My operating philosophy: Cadence | Ownership | Process

I install a repeatable flywheel of operational excellence:

Cadence
A rigorous Rhythm of Business—daily, weekly, and monthly operating cadence that surfaces execution risk early, before it becomes a board-level surprise.

Ownership
Managers own outcomes, not just activity. Forecasts are built bottom-up so leadership can commit without caveats.

Process
Qualification and execution are standardized before adding headcount, ensuring hiring is tied to capacity and real revenue impact—not hope.

The proof (Ekahau — SVP, Global Sales, 2019–2024)
	•	Revenue: Scaled $25M → $65M ARR in five years
	•	EBITDA: Increased $7M → $32M (margins ~20% → ~50%)
	•	Team: Built a 130-person global organization while reducing per-employee cost 25%

Selected wins
	•	Healthentic: Doubled ACV ($5M → $10M) and drove 10× pipeline growth through GTM transformation
	•	ControlCase: Delivered 34% YoY growth and 300% expansion revenue growth

Currently

Available for VP of Sales or Fractional GTM leadership with B2B SaaS companies $5M–$30M ARR. I also lead SalesGSS (revenue operating frameworks) and DigitalRegIntel (regulatory intelligence for AI/fintech).

The Senator perspective

Two terms as a Washington State Senator taught me the value of high-stakes negotiation and public accountability. I bring that same discipline to sales: clear ownership and execution when the pressure is real.

“Steve is ‘Instant Offense’ for sales—rare and valuable. World-class at creating strategic, data-driven sales teams.”
— Jeff O’Mara, CEO (Healthentic) / GM (Ekahau)

Steve Litzow

If revenue per employee is flat while headcount rises, you’re not scaling. You’re diluting.

Most $10M–$50M ARR teams are measuring the wrong thing.
They celebrate hiring.

Elite teams watch revenue per employee.

Here’s what 2026 is quietly proving:
Growth doesn’t stall because opportunity disappeared.

It stalls because attention fragmented.
New ICP.
New vertical.
New pricing model.
New feature set.
New partnership.
All rational.
All defensible.

Collectively? Expensive.

Revenue per employee isn’t a finance metric.
It’s a focus metric.

Bootstrapped SaaS companies at $1M–$3M ARR average ~$110K per employee.

Equity-backed peers average ~$94K.

Capital didn’t create the gap.

Discipline did.

Fragmentation increases decision latency.

Decision latency expands Signal-to-Action Time.

And once SAT expands, velocity stops compounding.
You don’t lose because you’re wrong.

You lose because complexity expands faster than discipline.

Pressure test your system:
• If you asked three reps to define your ICP, would they say the same thing?
• Do your top 20 deals look similar — or random?
• Has revenue per employee improved in the last two quarters — or are you hiring into flat output?
• When was the last time you killed an initiative?

Elite teams don’t run more plays.
They run fewer — with intensity.

Focus multiplies revenue per employee.
Complexity multiplies meetings.

Week 7 of the 2026 Operating Series.

Link in comments.

VP of Sales | Scaled $25M → $65M ARR | Operating Discipline for Growth & Scrutiny

No new rule last week.

That’s the risk.

On Feb 13, FinCEN quietly operationalized its whistleblower portal.

Now AML, AI governance, and digital asset supervision gaps can be reported directly to enforcement — before an exam ever starts.

This changes the timeline.

Enforcement is no longer tied to regulatory cycles.

It’s tied to internal observation.

An email.
A Slack message.
A deferred monitoring upgrade.

Those can now become time-stamped federal evidence.

The real shift isn’t rulemaking.

It’s attribution infrastructure.

When regulators look back 24–36 months from now, the question won’t be:

“Did you know the rule?”

It will be:

“Can you prove you supervised in real time?”

Documentation is no longer defensive.

It’s existential.

Full breakdown in this week’s Brief. (Link in comments.)

US enforcement is accelerating through whistleblower infrastructure.

EU regulation is accelerating through statutory documentation and logging requirements.

Different systems.

Same burden.

You must be able to prove:

• What management knew
• When it knew it
• How it assessed applicability
• What action (or deferral) followed

Frameworks don’t fail companies.

Missing chronology does.

Your deal didn’t lose to a competitor.

It died in a conference room.

40–60% of B2B deals end in “no decision.”

Not lost.

Just never aligned.

At $10M–$50M ARR, most teams still sell to a champion.

But the real sale is to the committee.

If a deal is single-threaded beyond day 45, your forecast isn’t aggressive.

It’s structurally optimistic.

This week’s issue breaks down how elite teams prevent ghost pipeline.

Comment PLAYBOOK and I’ll send it.

Marcos Rivera

Most B2B SaaS leaders build value.
But forget to capture it.

Let me guess:

- You’re guessing your price
- You’re losing revenue
- Scaling feels stuck

What if pricing could drive growth?

Here’s what I help you do:

→ Capture more value
→ Make pricing your edge
→ Build pricing confidence

Why should you trust me?

- 25+ years in tech pricing
- Ex–Head of Pricing at Vista Equity
- Priced 400+ SaaS products
- Author of *Street Pricing*
- Trusted by MBAs and SaaS CEOs

Beyond coaching, 

I’m an:

→ Investor 
→ Speaker
→ Entrepreneur 

passionate about helping businesses unlock their full revenue potential.

Ready to take control of your most powerful growth lever—pricing?

Checkout my featured section.

Founder and CEO

We help growth-stage B2B SaaS companies design the right pricing model to scale up

Ready to shift your pricing from guesswork to framework?

For the first time in my career, I lowered our growth forecast.

A few weeks into 2026, and I made a decision that felt counterintuitive: we're going to grow less this year. On purpose.

Here's my thinking.

I've been watching F1 lately, there's a scene in the new movie where Brad Pitt tells the pit crew: "Slow is smooth, and smooth is fast."

That line stuck with me.

What got us to 25 people and on the way to $10M bootstrapped isn't going to get us to the next stage. 

We're about to launch our first product. 
We're shifting from pure services to technology-enabled transformation.

That's a pivot. And you can't pivot at full speed.
The sports analogy holds up everywhere. 
Tennis, basketball, skiing, you have to slow down before you change direction. 

Get your balance underneath you. 
Build momentum. 
Then move.

Business is no different.

Here's what slowing down actually looks like for us:
→ Keeping quality at 98% satisfaction instead of chasing volume.
→ Reducing the number of engagement types. Fewer SKUs, less variability.
→ Saying no to projects that don't fit the middle of our fairway, even when the money's good.

Why? Because it's way harder to recover from a quality drop than a revenue dip. 
One bad quarter of delivery can undo years of reputation.

If you're considering a similar move, here's my framework:

1/ Identify the pivot. 
2/ Reduce variability first. 
3/ Protect what got you here. 
4/ Get alignment before you announce. 

The target is lower now. 
Less ambitious. 
But it's more achievable, and it sets us up for what's actually coming.

Sometimes slowing down is the most aggressive move you can make.

What's a decision you've made that felt counterintuitive but turned out right?

CEO of Pricing I/O • Award-Winning Author • Sought after Slayer of Bad Pricing

Everyone told me I was crazy to leave.

High-paying role at a PE firm. 
Direct access to a billionaire's inner circle. 
I was flying to portfolio companies on 24 hours notice, promising boards 18% revenue increase, and delivering.

But I was hitting airline status in two months flat, with a 4-year-old at home and a daughter on the way.

So I walked away and started Pricing I/O with a credit card and my savings.

That was the beginning. 

We're 25 people now, approaching $10M, and I still get a little stunned when I see how many seats we fill at team get-togethers.

I sat down with Mark Osborne, MBA, CEPA® on the B2B Growth Blueprint podcast and got into the full journey—the leap, how we actually scaled, and the leadership framework I use to run the business today.

Watch the full conversation:
→ https://skd.so/kPle2t

Most SaaS companies are pricing blind.

They copy competitors who are also guessing. 

They slap "AI-powered" on the pricing page and hope it justifies a premium. 

They build credit systems because everyone else is doing it, without understanding why credits work for Audible but might destroy their business.

And then they wonder why sales cycles drag, why customers push back on renewals, why the board keeps asking uncomfortable questions about unit economics.

We all have seen this pattern. Right?

→ The CEO who approved a "usage-based transformation" only to watch churn spike 40% because customers couldn't predict their bills.

→ The VP of Product who spent 6 months building an AI feature, then gave it away for free because nobody knew how to price it.

→ The founder who copied HubSpot's model without realizing HubSpot has 15 years of pricing iteration behind every decision.

Here's what I've learned: pricing isn't a simple math problem. 
It's a strategy problem disguised as a spreadsheet.

Is to understand the psychology behind why customers say yes, and structure their pricing to remove friction, not add complexity.

That's why I built this playbook.

A single page with the frameworks we actually use when we're in the trenches with B2B SaaS clients.

It's dense, but I can send you the high-res version. 
Comment "playbook" ↓

Today Satya Nadella leads a $3 trillion company with 228,000 employees.
But when he took over in 2014, Microsoft was stuck.

Losing mobile. 
Windows-obsessed. 
Falling behind Amazon in cloud. 
→ Market cap at $300 billion while competitors lapped them.

Most people expected a safe, incremental CEO.
Instead, Satya rewired the culture without burning it down.

Killed the stack-ranking system that turned teams against each other. 

Replaced "know-it-all" with "learn-it-all." 
Bet everything on cloud when Azure was still a distant second to AWS.

That bet alone now generates $75B+ in annual revenue.

But what I admire most isn't the strategy.

Technical depth. Emotional intelligence. Business instinct. 
Most leaders I've worked with have one, maybe two. Satya has all three, and deploys them quietly.

No theatrics. No ego. 
Just calm, steady decisions at a scale most of us can't comprehend.

He turned a legacy software company into the world's second-most valuable business by doing what every great leader must: read the room, commit to the shift, and bring the whole organization with you.

That last part, bringing people with you, is the hardest part of any transformation. Pricing, product, culture, doesn't matter.

I've seen it across hundreds of companies. 
The team leading the change matters more than the change itself.

A decade of selling B2B SaaS to PE firms teaches you something most pricing strategists never learn firsthand.

James joined us as a Pricing Strategist after years on the other side of the table.

If you've ever sold to PE, you know, they understand value as well as anyone, and they're ruthless about ROI.

That experience shaped how James thinks about pricing: always tie it back to quantifiable business outcomes. Never be vague about value drivers. Surface the trade-offs so clients can make better decisions, not just hear what they want to hear.

That mindset is exactly why we wanted him here.

What surprised him most about joining?
"We're a lean organization that punches well above its weight. Everyone on the team is incredibly sharp and moves fast."

He also mentioned being staffed on two client projects in his first week. That's not an accident, it's a vote of confidence in what a sales background brings to strategy work.

His mindset says it all.
Sales and product team alignment is the most crucial step in executing any pricing strategy.

Simple. True. And something most companies underestimate until it's too late.

Oh, and his karaoke song is "Escape (The Piña Colada Song)."

Make of that what you will.

Glad to have you on the team, James.

"Claude, let's code this SaaS, try not to hallucinate this time."

Honestly? We're getting there.

Recently we watched founders spin up products in weeks that used to take engineering teams 18 months.

→ Claude writes the code
→ Cursor ships the features
→ Bolt scaffolds the whole thing

But then the product is live, and someone asks: 
"What do we charge for this?"

That's where the vibe coding stops.
Because pricing isn't a code problem.

It's a "which metric scales with their success" problem.
It's a "what does your customer actually value" problem.
It's a "what does your board need this to say about your business" problem.

I've worked with 400+ SaaS companies. 
I've never seen a model spit out the right answer to those questions.

Not because AI isn't smart enough.

Because the answer lives in your customers, your data, your market, and someone who's seen enough patterns to know the difference between a pricing model and a pricing strategy.

That's still a human job.

If the pricing conversation is already giving you a headache, that's exactly what we do at Pricing I/O.

Let's talk.

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$285 billion wiped from software stocks in 48 hours.
The reason? Investors finally realized what we've been saying for 2 years, per-seat pricing breaks when AI agents replace human users.

Salesforce lost 7% in a day. ServiceNow, Adobe, Workday, all hit.

But here's what's wild: most SaaS companies I talk to are STILL running per-seat models with zero backup plan.

The "SaaSpocalypse" wasn't a surprise. 
It was a pricing model catching up with reality.

If your revenue model depends on headcount growth, and AI is shrinking headcount, and just like that: you have a monetization crisis.

"Rapid pricing experimentation" is dangerous advice.

I keep seeing the same pitch from billing platforms and entitlement tools: configure your pricing, launch a test, learn fast, iterate, repeat.

Sounds great in theory.

If you're selling a $9/month product to 100,000 users? Sure. 

Test away. Change that $9 to $9.99 and see what happens. 
You've got statistical significance and low stakes.

But if you're negotiating a $150K deal with a CFO at a Fortune 500?

→ Try explaining that your quote from last week was "just a test."
→ Try telling your sales reps that pricing changed again—third time this quarter.
→ Try building credibility when the prospect remembers seeing different prices six months ago.

Expertise over experimentation. 
That's my stance.

I'm not against testing. 
Testing is essential. 

But blind, rapid iteration creates more problems than it solves: internal confusion, external credibility risk, sales teams who don't know what to sell, and customers who don't know what to trust.

The answer isn't more speed. 
It's more intention.

Informed. Measured. Deliberate.

If your team is about to make a pricing decision too fast, that's exactly what we work through at Pricing I/O. Drop a comment or DM me.

Most SaaS companies blame product for churn.
But the data usually points somewhere else: pricing.

3 steps. 10 minutes. 
You'll know if churn is pricing-driven or product-driven.

Segment by cohort. Compare NRR vs. LTV. 
Read churn surveys for the real signals.

If customers say "can't justify cost", that's not a product problem.

2026 is the year the pack separates.
Not with a dramatic crash, more of a slow exposure.

On one side: companies that are deliberate about AI integration, honest about their metrics, and strategic about pricing.

On the other: the copycats. The aimless AI adopters. The ones chasing "Wishful Thinking ARR" with creative revenue definitions and 50x valuations.

The fallout we expected in 2025? 
I think it shows up in 2026. 

Here's why:
→ AI scrutiny goes up (budgets need justification now)
→ Differentiation pressure increases (the checkbox AI gets exposed)
→ Companies under pressure make desperate pricing moves

And here's the opportunity: the smart operators will start picking up technology AND talent from the companies that couldn't adapt.

Acqui-hiring in 2026 is going to be massive.

The question is: which side of the separation are you building for?

The best pricing leaders are readers.
And these are the 12 books every SaaS pricing expert should read.

Save this one to read later ↓

→ Month 1:
Monetizing Innovation
The Pricing Roadmap

→ Month 2:
Street Pricing
Blue Ocean Strategy

→ Month 3:
The Cold Start Problem
Hooked

→ Month 4:
The Go-To Market Handbook
The Lean Startup

→ Month 5:
Influence
Predictably Irrational

→ Month 6:
The Art of Pricing
The Subscription Boom

If you want to go deeper than books, this is what we work on every day at Pricing I/O.
Drop a DM and let's talk.

After working with 400+ SaaS companies, I see three types when it comes to AI integration, and only one of them survives the next 2 years.

Most companies say they're using AI.
Very few can explain why.

The difference isn't budget. It's not talent either.
It's whether AI is a checkbox or a strategy.

Some companies know exactly where AI fits in their pricing, packaging, and go-to-market. 

They've mapped the ROI. 
They've planned the process change.

Others bolted AI onto a roadmap with no monetization strategy behind it, and their boards are starting to notice.

Where does your company fall on this spectrum?

I almost lost myself to AI news last year.
Every day there was something new. 

OpenAI did this. Anthropic launched that. Google's catching up. Startups raising at 50x revenue.

I was reading everything. 
Trying to understand every perspective. 
Watching every announcement.

And then I noticed something: 
I was paying less attention to my team.

The conversations were shorter. 
The check-ins were surface-level. 

I was physically present but mentally somewhere else, chasing the next headline, the next hot take, the next "you need to know this" thread.

FOMO was pulling me away from the work that actually matters.

Here's what I've been obsessing over instead: clarity.

Not mission statements. Not OKRs. 
Actual clarity, where your team can articulate what they're doing, why they're doing it, and how it connects to where you're going.

It sounds simple. 
It's brutally hard.

I've started asking my direct reports one question:
"Do you understand what we're doing and why?"

If they have a different point of view, I want to hear it. 
If they're confused, I need to know. 

A 10-second answer tells me everything: 
"Yes, I get it, I think we're going the right direction." 

Great. But more often, that question opens a door to something I was missing.

Here's my test:
→ If you have 5 direct reports and all 5 say the same thing about your direction—high five, you're leading well.
→ If all 5 have completely different views of what you're trying to do? That's not a them problem. That's a you problem.

People can feel when you're paying attention. 
They can also feel when you're not.

Forget FOMO. Focus.

2026 isn't the year SaaS dies.

It's the year people finally realize AI needs SaaS as much as SaaS needs AI.

Distribution, data, workflows, customer trust, none of that disappears because ChatGPT exists. 

But the SaaS companies scrambling to slap "AI-powered" on their pricing page without rethinking what they actually deliver? Those are the ones in trouble.

We've watched this play out across hundreds of companies.

Companies treating AI like a feature are missing the real forcing function, the question they've been avoiding for years: what outcome are we actually selling?

Seat-based pricing made sense when humans were the unit of consumption. 

When AI agents are doing the work, you're not selling seats anymore, you're selling results, throughput, outcomes that scale beyond headcount.

Most SaaS companies haven't touched their pricing model in years. 
AI just made that procrastination expensive. 

→ Boards are asking harder questions. 
→ Valuations are getting squeezed. 
→ And every month without a clear answer is revenue left on the table.

To surf the hype in 2026, get deliberate about monetizing what AI actually delivers.

That's what we spend every day working on at Pricing I/O, and the urgency we're hearing from founders and boards right now is unlike anything from the last few years.

The window to get ahead of this is open. It won't be for long.

I had to look in the mirror and ask myself a hard question.
Am I drinking my own Kool-Aid?

I've sat in rooms with founders who had their goggles on. 
Convinced they're smarter than everyone. 
Convinced the market is theirs for the taking.

And I've watched them fail.

Smart. Ambitious. Dedicated. Motivated.
Still failed.

So when I started building our new product, I made myself three promises:

1/ Assume there won't be a warm reception.
2/ Assume my assumptions are wrong.
3/ Assume this is a longer journey than I think.

Mike Tyson said it best: 
"No plan survives the first punch in the face."

We're going to get punched in the face. 
Every product does.

The question isn't whether it happens. It's how we react.

So instead of chasing a blowout launch, I'm building systems. 

Feedback loops. 
Prioritization frameworks. 
Quick cycles to learn and pivot.

How do I figure out how to figure out stuff?

That's the real question.

If we get a blowout launch? Hallelujah.

But I'm planning for the worst and hoping for the best.

Building something new is freaking hard. 
And it's full of trapdoors.

What's one assumption you're making about your business that might be wrong?

I think Mark Benioff is overrated.
I'll say it out loud.

Look, Salesforce is the godfather of SaaS. 
Many people give it that title, and it's earned. 

They pioneered cloud software. Built a $40B+ company.

But I think that was more Mark's team and the great people he had around him than Mark himself.

He's good at sales. He makes smart decisions. He’s a pioneer.  
I'm not saying he's bad.

But I lost a lot of respect for him when he said AI would be easy. 
That he could sell the world on his AI overnight.

That's obnoxious.

AI isn't easy. Anyone who's actually building with it knows that. 
Anyone who's helping companies integrate it knows the complexity, the change management, the friction.

Saying "AI is easy" tells me you're selling, not building.

I'd rather follow leaders who are thoughtful than leaders who are loud.
Give me Satya Nadella's calm over Benioff's bravado any day.

Pricing for the wrong thing is one of the most expensive mistakes I see.
(And still most companies miss this completely)

In a PLG motion, pricing does the heavy lifting early. 
→ It's the packaging, the free tier boundary, the upgrade trigger that converts users before a human ever gets involved.

In a sales-led motion, pricing shows up late. 
→ It's a negotiation lever, a discounting battlefield, and often an afterthought bolted onto whatever the rep promised on the call.

I've seen 400+ SaaS companies try to use the same pricing playbook for both motions. 

It doesn't work, because the moment where pricing creates or destroys value is fundamentally different.

The consequences cascade:
→ Your packaging
Does it need to sell itself on a webpage, or does it need to survive a 6-month procurement process?

→ Your discounting exposure
PLG has almost none. Sales-led can hemorrhage 20-40% if there are no guardrails.

→ Your expansion path
PLG expands through usage and upgrades. Sales-led expands through rep-driven upsell conversations.

→ Your pricing team's focus
Optimizing conversion rates vs. optimizing deal structures.

Neither is wrong. 

Your go-to-market motion dictates where your pricing has leverage.

If you're not sure your pricing is built for your motion, that's the first thing we diagnose at Pricing I/O. 

To book a free discovery call drop me a DM.

Most companies wait until something breaks to revisit pricing. 
Here are the 7 signals it's time to take a closer look.

In this video I'll talk you through:
→ Triggers that indicate pricing needs attention
→ Why "not the right time" is costing you money
→ Common patterns from 400+ SaaS companies

#saas #pricing

When people ask who I'm being inspired by, I don't have a good answer.

I never looked for figures to follow.
No heroes. No role models I'm trying to copy.

Just me, trying to make more good decisions than bad decisions. 

Keep learning forward. 
Treat people right.

That's it. That's the whole philosophy.

I like outside perspective. I get inspired by others. But what works for them doesn't necessarily work for me.

And I think that's okay.

Not everyone needs a leader to chase.

Some of us just need to stay honest with ourselves about where we're strong and where we're not.

Be introspective. 
Be blunt with yourself. 
Make trade-offs intentionally.

In the end, business is all about getting people to do stuff for you. 

→ Engineers to build for you
→ Employees to work for you
→ Customers to buy from you

Once you figure out how to do that, there's really no limit to what you can do.

No heroes required.

SaaS Founder: Stop copying competitor pricing pages.

That pricing page you're copying was built for a completely different business.

Here's how to fix it.

Watch more pricing insights here https://skd.so/E9ur5M

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