Strategy & GTM Advisor | Follow me for strategy, growth, and leadership tips.

I lead Growth at Pricing I/O, the leading hands-on SaaS pricing consultancy.

Our track record:
→ 400+ software companies
→ 98% client satisfaction
→ 15x average Year 1 ROI

Before joining Pricing I/O, I was their client. I spent 11 years at Mercatus, a private equity software company:

→ Started as employee #5
→ Navigated multiple promotions
→ Eventually became Global Head of Product & Marketing
→ Built global teams and owned pricing and GTM strategy
→ Hired Pricing I/O in 2019, a key inflection point
→ Delivered Avg 85% YoY ACV growth 
→ Led to a 9-figure exit to State Street (Fortune 250)
→ Company now manages $1.8+ trillion in private equity assets for the world's largest investors

I lived the pricing struggle every leader fears:
→ Sleepless nights: Are we leaving millions on the table?
→ Boardroom wars: Everyone has an opinion on price
→ Investor pressure: Triple revenue AND keep customers happy

If your feel the same way at your software company, let's talk.

Connect:
→ Book a FREE pricing strategy call at pricingio dot com
→ Join The Moat, my free newsletter for B2B leaders for an inside look at our growth playbook.

In 2012, Best Buy should’ve died:

Wall Street called it “dead walking.”
The stock hit a 10-year low.
They lost $1.7B in a single quarter.

The industry even named the problem: “showrooming.”

Customers walked into Best Buy, touched the TV, scanned the barcode, and bought it cheaper on Amazon - while standing in the aisle.

The advice to the incoming CEO Hubert Joly was obvious:
→ Close stores immediately
→ Fire thousands of employees
→ Accept that physical retail is dead

He did the opposite.

Joly launched "Renew Blue" with a simple insight:
"Showrooming proves customers want the store experience. They just don't want to overpay for it."

His counterintuitive solution:

1. Price Match Guarantee
↳ This didn’t win the sale.
↳ It removed the only reason customers had to leave.

2. Invested in employees
↳ While others treated staff as a cost center.
↳ Joly invested in expertise customers actually valued.

3. Turned stores into brand showcase partners
↳ He realized stores are media channels not just warehouses
↳ He got Samsung, Microsoft, Google, and later Amazon to pay for floor space to showcase their tech.

The result:
→ Stock rallied from $12 (2012) to $70+ (subsequent years)
→ Returned to profitability
→ "Showrooms" became an asset, not a liability
→ Became the go-to partner tech brands.

The lesson:
The leaders who win don’t eliminate their disadvantages. 
They reframe them and build a strategy around what others misinterpret.

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Ali Mamujee

In 2013, Adobe made the most hated pricing decision in tech:

~ 50,000 customers signed a petition begging them not to do it.
They ignored every single one.

For years, Adobe sold its creative suite in a box:
Pay once. Use it forever.

It worked - until it didn’t.

Customers skipped upgrades (the old version still worked)
Revenue spiked at launches and sagged in between
The upfront price locked out millions of would-be users

So in May 2013, Adobe CEO Shantanu Narayen announced:

CS6 would be the last major perpetual release.
Future innovation would ship through Creative Cloud.

The response was intense. Forums were flooded.
Long-time customers were angry.

And the financial impact was real.
Net income fell from $832.8M to $290.0M - a ~65% drop.

But Adobe wasn’t just changing prices.
They were changing who could enter.

Narayen faced a choice: listen to 50,000 angry customers or risk short-term pain for long-term transformation. He chose the risk.

By moving to subscriptions, they:
- Lowered the barrier to start
- Created continuous value instead of one-time upgrades
- Built an always-on relationship with customers

Over time, that changed everything.

→ Stock: ~$37.68 (2012) → $444.68 (2024)
→ Revenue: $4.4B (2012) → $21.5B (2024)
→ Subscribers: 37M+ (2024)

The lesson isn’t that subscriptions magically create growth.

It’s that pricing power comes from removing friction for the right customers.

When you make it easier for people to start, stay, and succeed, revenue follows.

♻️ Repost for your network
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The advice I needed the most when I felt incredibly lost:

Pursue yourself.

Sometimes feeling lost is that pause before clarity.

Here are 3 truths that helped me:

1. Find What Lights You Up 
 ↳ Pay attention to what energizes, not just what pays.
 ↳ Trust the moments that make you feel alive.

2. Break Free From Others' Dreams 
 ↳ Stop chasing someone else's definition of success.
 ↳ Your path doesn't need to make sense to anyone else.

3. Start Small, Start Now 
 ↳ Take one tiny step toward what interests you.
 ↳ Let action clear the fog of uncertainty.

Your gut knows where you need to go. 

Trust that voice – it's been right all along.

♻️ Repost for others who need to hear this.
 
Quote credit: @elevated states

In 1962, Ford spotted a generation priced out of their dreams:

A wave of young buyers (baby boomers) wanted something sporty. Something that felt like freedom.

But the options were out of reach: 
Corvette: ~$4,000. 
European sports cars: even more.

Ford’s research showed these buyers would pay up to $2,500 for the right car: style + identity, without luxury-sports pricing.

Most automakers would've tried to build a cheaper Corvette: strip features, cut corners, compete on specs.

Ford took a different bet.

Lee Iacocca, Ford's VP and the internal champion for this vision, realized these buyers weren't buying horsepower.

They were buying identity. Style. Customization. A car that said something about who they were.

So the Mustang was designed around that insight:
→ Style over specs (emotion beats horsepower)
→ Customization over bundles (let buyers make it theirs)
→ 4 seats, not 2 (sporty and practical)
→ Built on the Falcon platform (so the economics worked)

They didn't build a cheap sports car. 
They created a new category: the pony car.

Result:
→ Launched April 1964 at $2,368
 → Forecast: 100,000 in year one
 → Actual: 418,000
 → 1M+ in 18 months

The lesson:

That's what value-based pricing really means:
Pick the market you want. Pick the buyer you're serving. 
Then design the offer that wins at that price point.

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Patrick's strategy for Colossus hit different. 

(Colossus is a premium print magazine + media company run by Patrick O'Shaughnessy - it’s one of my favorite things to get in the mail.)

He wrote: "I don't like to destroy competitors. 
I just feel bad that it's not unique enough."

That’s always been my philosophy.
If we’re being compared, we haven’t built something distinct enough yet.

I see too many B2B companies stuck in feature warfare - matching competitors point-by-point, racing to parity.

The problem isn't that they're losing.

It's that they're playing a game where "winning" still leaves them commoditized.

Most strategies sound like:
"We'll be faster."
"We'll be cheaper."
"We'll outwork them."

But the best strategies don't start with comparison.
They start with: What are we building that didn't exist before? 

When your offering is truly unique:
- Price objections disappear
- Competitors become irrelevant
- Customers can't find alternatives

The best strategy isn't about winning the race.
It's about running a different race entirely.

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If your B2B deals keep stalling, run these 3 checks:

These checks come straight from our sales-call reviews with trusted advisors.

This is for complex, multi-stakeholder B2B cycles.

1) Are all the right people in the room?
In complex B2B purchases, decisions rarely sit with one person.
Buying groups average ~5.4 stakeholders - each with different incentives and concerns (CEB).

That’s why stalled deals often sit with a single champion: someone who loves the idea but doesn’t own the budget.

Test: If your champion left tomorrow, would the deal survive?

Fix: Keep your champion empowered but earn access to the people who weigh in and sign off.

2) Can you make the future state concrete?
Deals drag when the customer keeps re-explaining themselves.
Calls spread out. People rotate in. Memory resets.

Test: On every call, can you say:
→ Here’s the problem you described
→ Here’s what “better” looks like (in your words)
→ Here’s the gap between now and there

Fix: Restate the before/after every call. Not once. Every time.

3) Have you put a number on their pain?
Most reps stop at “that sounds painful.”
But pain without numbers rarely creates urgency.

Test: When they say "discounting is out of control," do you know the actual cost?

Example: A $100M SaaS company with a 5% discounting gap leaks $5M/year.
Make it real:
→ ~$400K/month
→ ~$20K/day 

Suddenly a $200K engagement isn’t “expensive.” It’s a 10 working-day payback.

Fix: Don't build a fancy ROI calculator. Get one simple number they agree is real.

If a deal is stuck in “maybe,” it’s usually failing one of these checks.

Run the diagnostic. Fix the failure point. Watch it move.

♻️ Repost if your sales team needs this
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A $100M+ company wrote this in an RFP they sent us:

“We’ve created the appearance of modern pricing with none of the behavior.”

Most honest thing I've read.

They had done everything “right”:
→ Moved from seats to usage
→ Launched a self-serve tier
→ Built enterprise packaging

On paper, it looked modern. But underneath:

→ Sales still discounted like it was 2015
→ Customers still couldn’t explain what they were paying for
→ Finance still couldn’t forecast revenue with confidence

The model changed. The behavior didn’t.

At Pricing I/O, we're seeing this pattern everywhere:

Companies adopt the language of modern pricing - usage-based, PLG, value-aligned - without building the system to support it.

So what happens?

→ The new pricing sits on a page no one actually uses
→ Sales defaults to whatever closes the deal
→ Customers feel the disconnect and push back harder

The gap between “announced pricing” and “real pricing” quietly grows.

And leadership wonders why the transformation isn’t working.

Here’s the truth most teams miss:
Pricing transformation isn’t a launch. It’s a rewiring.

It touches:
→ How sales gets paid
→ How CS talks about value
→ How finance measures success
→ How product designs packaging

Change the model without changing those and the organization pulls it back to the old way.

If your pricing looks modern but still feels stuck, the problem probably isn’t the model. It’s everything around it.

♻️ Repost if this hit close to home
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Your discount tiers aren’t protecting revenue.
They’re teaching buyers how to negotiate against you.

I see it all the time:
Deals cluster at the exact same numbers - 10%, 15%, 20% off list.

Leaders look at that and think: “Good. Discount discipline.”
What it usually means: your approval bands became the price.

- Reps can approve up to 10%
- Managers up to 15%
- VPs up to 20%

Buyers learn this faster than we think.
They stop asking, “Is this worth the price?”
And start asking, “Who do I need to talk to for 20%?”

You’re no longer pricing to value.
You’re pricing to whoever can approve the biggest cut.

The fix is simple: 
Give to get (no discount without a trade)

Make the trade pre-approved so reps don’t improvise:

- 10% = annual upfront or a firm close date
- 15% = multi-year and/or bigger seat commit
- 20% = reduced scope + exec sponsor + expansion clause

Now reps stop thinking, “How much can I discount?”
They start thinking, “What can I get in return?”

That one shift protects margin and shortens cycles without turning sales into red tape.

Every discount you approve without a trade teaches buyers to ask for more. Stop teaching.

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VP Growth of Pricing I/O

A higher price can literally make the same product feel better:
(according to brain scan)

Not “feel” as in marketing fluff.
Feel as in: your brain processes it differently.

In a 2017 experiment (INSEAD + University of Bonn), people tasted the same €12 red wine but saw three different price tags:

- Wine bottle #1: €3
- Wine bottle #2: €6
- Wine bottle #3: €18

The “€18” wine was rated as more pleasant.

And brain scans (MRI) showed price cues shifted activity in reward/valuation-related regions.

Same liquid. Different reality.

The point isn’t “charge more.” 
The point is: price is part of the experience.

The pricing lesson for SaaS:

If you underprice (or over-discount), you don’t just lose revenue.

You often create:
- more skepticism (“what’s the catch?”)
- more nitpicking (“why doesn’t it do X?”)
- less patience during onboarding (“not worth the time”)

Because the brain uses price as a shortcut for value.

So the real question isn’t:
“What’s the minimum I can charge?”

It’s:

“What price supports the value story customers need to believe - so they actually experience the value?”

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Source: Schmidt et al. (2017), Scientific Reports - INSEAD & University of Bonn

In 2008, Airbnb was failing.

They had almost no traffic. 

Co-founders (Brian Chesky and Joe Gebbia) had racked up $20,000 in credit card debt each. 
 
And they’d made less than $5,000 from the actual Airbnb business.

So they did something that sounds like a joke…
They made election cereal.

Two boxes: Obama O’s and Cap’n McCain’s. 

They printed and hand-assembled 1,000 boxes, and sold them as limited edition collectibles for $40 each. 

The press ate it up.
Obama O’s sold out. 
Cap’n McCain’s didn’t. 

But the stunt did what the product couldn’t (yet):
It generated $20,000–$30,000 - more than the company had made from bookings. 

Then came the interview that changed everything.

Paul Graham - the founder of Y Combinator, the startup accelerator - didn't love the Airbnb idea.

Until he heard the cereal story.

His line: "If you can convince people to pay $40 for a $4 box of cereal, you can probably convince strangers to stay in other strangers' homes."

He called them "cockroaches."
They just wouldn't die.

Then → Now
Airbnb’s FY2024 revenue was $11.1B. 
And it generated $4.5B in trailing-twelve-month free cash flow. 

The lesson for founders:
Runway isn't only money in the bank. 
It's your ability to manufacture value when the core model isn't working yet.

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I spent 11 years at Mercatus that sold for 9 figures.
If I had to credit one framework, it’d be this one slide.

Back in 2015, Peter Cohan trained our team at Mercatus.
(He wrote Great Demo, Doing Discovery, & Suspending Belief)

He taught us the Situation Slide (see image 👇)
Real example + editable slide link in the comments 👇

If you run B2B sales calls, use this as the North Star for discovery.

It forces clarity before you pitch.
Who it’s for. What’s at risk. Why now. And what it’s worth.

It didn’t just improve sales. It became our storytelling framework for the entire company.

→ Sales used it to qualify pipeline 
→ Product used it to prioritize the roadmap 
→ Marketing pulled messaging directly from it
→ Customer Success referenced it during onboarding 

Fast forward to Pricing I/O: our pipeline nearly 2x'd - and win rates had to follow. So I brought it back.

It’s the fastest way I know to spot unqualified pipeline early.

Incomplete slide = incomplete qualification. 

♻️ Repost if your sales team needs this
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Mailchimp’s accidental move 5x’d growth in a year.

Here’s how it happened:

In 2009, Mailchimp had $0 in funding.
Their competitor, Constant Contact, had raised $100M+.

Mailchimp couldn’t outspend them.
So co-founder Ben Chestnut needed a different way to grow.

Ben’s plan: split Mailchimp into two products.
→ Free for building email lists
→ Paid for sending emails

But the lead engineer said the codebase was too complex to split.

The engineer’s workaround:
“Instead of two products, I’ll make it one but free up to a limit.”

Ben’s response: “We’re running out of time. Do it.”

Ben later said they didn’t want to give anything away for free:
 “We wanted to charge the hell out of people.

That’s it. No grand strategy.
An engineer’s shortcut became the freemium model.

The results: 

→ Users: 85k → 450k in 12 months (≈5x)
→ Profit increased by 650% 
→ CAC dropped to under $100

Here's what made it work:

Free wasn't charity. Free was the funnel.
Every email sent by a free user carried Mailchimp's badge. 
Customer usage became the marketing engine.

In 2021, Intuit acquired Mailchimp for $12B.

The lesson:
Freemium only works when "free" creates a loop: 

→ What action delivers value fast? 
→ What action spreads the product? 
→ What moment naturally triggers "now I'll pay"?

If your free tier doesn't answer all three - it's not freemium. It's just free.

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AI was supposed to deliver massive value

Instead it’s delivering massive shelfware.

AI has become the easiest justification for a price increase.

But a lot of customers aren’t adopting it. They’re hesitating.

Because they don’t trust they’ll stay in budget.

Some numbers that explain why:
→ 68% of vendors restrict AI to premium tiers 
→ AI add-ons can add 30–110% to the base cost 
→ Orgs use only 47% of their SaaS licenses 

And the pattern looks like this:

Vendor: “We added AI. Price goes up.”
Buyer: “Fine. We need to stay current.”
Finance: “Why did spend jump?”
Users: “I’m not clicking that - what if it charges us?”

One pricing strategist put it perfectly:
“Usage stopped not because of price, but because admins didn’t trust they’d stay in budget.” 

If customers are afraid to use what they’re paying for, you didn’t create value. You created anxiety.

The best pricing doesn’t maximize what you can charge.
It maximizes what customers will actually use.

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How to sell your most expensive plan:

Change what it’s compared to.

Behavioral economist Dan Ariely showed this in an experiment.
He tested The Economist’s subscription options with 100 MIT students:

→ Web Only: $59 
→ Print Only: $125 
→ Print + Web: $125

With all three options available:
→ 16% chose Web-only
→ 0% chose Print-only
→ 84% chose Print + Web

Then he removed the "useless" Print-only option.

The results flipped:
68% chose Web-only while 32% chose Print + Web

The high tier went from the clear favorite to the minority choice just by removing an option nobody wanted anyway.

People decide based on what something sits next to.

If your high tier plan feels expensive instead of worth it, look at the context you're giving it.

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The strangest thing happened as I look ahead to 2026:

I have the least anxiety about work I’ve ever had.
Yet I feel more motivated than ever.

That surprised me.
Usually, ambition brings pressure with it.
This time, it brought clarity.

Stepping away at the end of the year - slowing down, spending time with family, creating space to think - helped that clarity surface. It made the priorities obvious.

Here's what's getting my attention in 2026:

At work:
- improving our win rate by making sales trusted advisors
– building the right awareness before buyers ever reach out
– building a growth team that’s hungry and aligned

Outside of work:
– health comes first
– deeper, face-to-face relationships
– more intentional time with family while the window is still open

Thank you all for being part of the journey.

Wishing you a steady start and a very happy new year

P.S. What’s getting the majority of your attention this year?

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