Chase Dimond

Top Ecommerce Email Marketer & Agency Owner | We’ve sent over 1 billion emails for our clients resulting in $200+ million in email attributable revenue.

I help brands make more money with email marketing.

I’m a Co-Founder of Structured, an ecommerce email marketing agency. Since launching in 2018, our team has helped brands send billions of emails and generate over $200M in email-attributable revenue.

We’re a top agency partner for platforms like Omnisend and Klaviyo.

Shopify featured me as a top email marketing influencer. I’ve also received LinkedIn’s Top Voice Award for Email Marketing, and Favikon has ranked me as the top email marketer across social media.

Some of the brands we’ve worked with include:

Poo~Pourri
Eight Sleep
Health-Ade
Mixtiles
Vessi

If you’re looking to hire an experienced email marketing agency, you can reach me here:

chase@chasedimond.com

——

Outside my agency, I run a number of other fast-growing businesses. I’m fortunate to have over 750,000+ followers and subscribers across my social channels and email newsletter.

I’ve worked with companies including:

LinkedIn
Amazon
TikTok
Gamma
Alibaba
Zapier
ClickUp

I work with a small number of paid sponsors and partners each year.

If you’re interested in exploring a potential fit, please email me with details:

chase@chasedimond.com

Founder

My newsletter is your no BS guide into what's working in email marketing - I'll give you the latest tips + tactics to help you drive more revenue from your email marketing channel. 

Sign up (it's free) here: https://chasedimond.com/chase-email-newsletter

Leadership isn't climbing the ladder. 

It's pulling others up with you.

But here's what most managers get backwards:

They serve upward, not downward. 
They protect their own reputation, not their team's. 
They take credit for wins and deflect blame for losses.

The best leaders flip this entirely.

Here's how to lead from beside, not above:

1️⃣ Share the risk, not just the reward 
↳ Put your reputation on the line for their ideas 
↳ Take accountability when experiments fail

2️⃣ Learn in public alongside your team 
↳ Admit when you don't know something 
↳ Show growth happens at every level

3️⃣ Fight battles together, not for them 
↳ Teach them to advocate for themselves 
↳ Stand shoulder-to-shoulder in tough conversations

4️⃣ Celebrate their wins as team victories 
↳ Amplify their voices in leadership meetings 
↳ Make their success the team's success

5️⃣ Build their confidence, not dependence 
↳ Ask "What do you think?" before giving answers 
↳ Help them trust their own judgment

Great leaders don't just reach the top.

They clear the path for their team to get there too.

Defend your people. Develop your legacy.

♻️ Repost to inspire someone 

Сredit: Carmen Morin ( go follow her )

Top Ecommerce Email Marketer | $200M+ Generated via Email

Take the risk.

Because here’s the math:

If it works → Happiness.
If it fails → Wisdom.

If you do nothing → Stagnation.

Why smart founders take bets:

• Action produces data
• Data reduces fear
• Experience builds judgment
• Judgment compounds

Example:

Apply for the stretch role.
Pitch the bigger client.
Ship the imperfect version.

Worst case?
You gain feedback most people never see.

Best case?
You change your trajectory.

Risk is a teacher.

Silence is not.

Next time you hesitate, ask:

What do I gain if I try?

Credit: TheArtidote on Twitter/X

Most people quit right before it works.

Because effort and reward do not move at the same speed.

Years 1 to 2:

You are bad.
You know it.
Everyone else knows it.

Good.

You are building muscle.

Year 3:

You are decent.
Still invisible.
Doubt gets louder.

This is the danger zone.
Most people exit here.

Year 4:

Your skill is real.
Your voice is clear.
Your network trusts you.

Now one catalyst matters.

A post.
A partnership.
A product launch.

And it looks sudden.

But here’s what really happened:

You compressed 4 years of learning into 30 days of output.

Example:

Builder ships 50 small tools over 4 years.
None break 1k users.

Tool #51 solves the right pain at the right time.
Hits 100k users in 2 months.

People call it overnight.

They did not see the first 50.

The playbook:

1. Treat early years as paid training.
2. Ship in public.
3. Build assets, not moments.
4. Stay until the math flips.

The lag is the price.

Pay it.

If you are in year 2 or 3, this is your sign to keep going.

Great leaders don’t need fans. 
They need challengers.
Fans protect ego. Challengers protect future.

(Credit: Mike Leber)
(Image credit: Eric Partaker)

Early in my leadership journey,
I mistook quiet rooms for strong alignment.

No pushback.
No friction.
Nodding heads.

I thought I was leading well.
I wasn’t.

People weren’t aligned.
They were careful.

And careful teams don’t build bold companies.

If no one challenges you,
you might not be respected.
You might be avoided.

That’s not leadership.
That’s authority on paper.

The higher you rise,
the less truth you automatically hear.

People filter.
They soften.
They protect ego instead of mission.

And slowly ...
you start believing your own narrative.

That’s how smart leaders become stagnant.
And confident leaders become fragile.

Strong leaders design for challenge 👇

1. Seek truth, not comfort
→ Surround yourself with thinkers, not echo chambers.

2. Ask open questions
→ “What am I missing?” is a power move.

3. Stay curious, not defensive
→ Curiosity signals strength. Ego signals fear.

4. Reward dissent
→ Publicly thank the person who challenges you.

5. Model vulnerability
→ Admit mistakes. It opens the door for honesty.

6. Celebrate better ideas
→ Especially when they replace yours.

7. Promote the brave, not the agreeable
→ Advance the voice that risks friction for progress.

8. Hire for courage
→ Skills matter. So does backbone.

9. Put data above hierarchy
→ Let evidence outrank seniority.

Policies shape culture.
But your reaction reveals it.

Here’s the real test:

When someone challenges you,
does your body tense ...
or does your curiosity rise?

Great leadership isn’t about agreement.

It’s about being brave enough to be wrong.
And smart enough to grow from it.

If no one challenges you, 
you’re not leading. 
you’re just managing an echo.

Be the leader who can handle the truth.
And build teams brave enough to offer it.

Perfection is just fear in a nice outfit.

Make it exist first.
Make it better later.

Image credit: itsme_urstruly on Twitter/X

Most of what you fear will never happen.

And what does happen is survivable.

Break fear down:

Fear of death
Out of your control.

Fear of shame
People forget fast. They move on to their own lives.

Fear of losing everything
You rebuild. Humans are wired to adapt.

Here is the 3 Step Fear Audit:

1. Define the worst case clearly
Not vaguely. Specifically.

2. Ask, can I recover?
In most business and career decisions, yes.

3. Calculate the cost of inaction
Regret compounds. Avoidance compounds.

Example:

Launch the idea.

Worst case
Low traction. Public flop.

Reality
You gain feedback. Improve. Try again.

Fear says permanent damage.

Reality says temporary discomfort.

Keep climbing.

Most ceilings are mental.

Image credit: iamfearlesssoul on Twitter/X

A fake caring culture is worse than a toxic one.
At least with toxicity, you know where you stand.

Fake caring hides behind smiles.
It says "we care", but means "please don’t make this uncomfortable".
It praises your work in meetings...then ignores your feedback after.

It’s leadership with empathy in words,
and apathy in action.

Here’s how fake caring shows up at work:

1️⃣ "We hear you" → but nothing changes.
2️⃣ "We’re like a family" → until KPIs drop.
3️⃣ "We value feedback" → unless it’s critical.

The result?
Distrust. Burnout. Quiet quitting.

Because pretending to care kills trust faster than open conflict ever could.

Real care isn’t a slogan.
It’s honesty, follow-through, and doing the right thing even when it’s inconvenient.

What’s one small action leaders can take this week to show they genuinely care? 👇


Image credit: Lorenzo D.

Sometimes we underestimate the quiet power within us.

We look at challenges and think
this might be too much.
Too difficult.
Too far beyond what we can handle.

But often the real limit is not the challenge.

It is the story we tell ourselves about what we are capable of.

(Credit: Christian Kampf)

Courage rarely arrives as a loud moment of strength.

More often it is something quieter.
A small inner voice that says
try one more time.
take one more step.
keep going.

And step by step we discover something remarkable.

We are far more resilient.
Far more capable.
Far stronger than we ever believed.

Sometimes courage is simply the decision to believe in that possibility.

Can I share something uncomfortable?

Doubt is louder than effort.

I’ve seen talented people stall
because they kept second-guessing every move.

And I’ve seen average ideas succeed
because the person behind them believed hard enough to execute fully.

Belief doesn’t guarantee results.

But hesitation guarantees small ones.

Here’s the shift:

Stop asking, “What if it fails?”
Start asking, “How would I move if it succeeds?”

Because you make different choices from belief:

• You follow up.
• You raise your rates.
• You apply anyway.
• You speak up in the room.

Momentum favors the committed.

Not the cautious.

You don’t need blind faith.

You need aligned action.

Are you building from belief…
or protecting yourself from disappointment?

Quote Credit: Leadersonlyco

The most influential leaders aren’t the loudest in the room.

They’re the ones who make others feel seen and respected.

Your communication style, empathy, and respect for others don't just shape your reputation.

They build bridges, foster collaboration, and create a positive work environment for everyone.

Active listening makes others feel valued.
Constructive feedback shows you care about growth.
Kindness and respect build trust and rapport.

It’s in the words you choose and the way you treat people.

That’s where real influence starts.

Quick thought:

The dream isn’t the hard part.

The discipline is.

Anyone can imagine the outcome.

Few commit to the inputs.

Big results are built quietly.

Early mornings.
Tight standards.
Consistent reps.

And humility?

That’s the anchor.

It keeps you learning.
It keeps you improving.
It keeps you coachable.

Ego stalls growth.

Humility accelerates it.

Dream big.

But work in silence.

Image credit: Daily__wisdom_ on Twitter/X

Most ads fail for one simple reason:

They focus on the product instead of the person.

Great copywriting flips that.

It’s not about sounding clever.
It’s about making people feel understood.

Here are a few timeless copywriting principles that still drive results today:

1️⃣ Sell what people want. Deliver what they need.
People buy the promise first.
But they stay for the real value.

2️⃣ Features tell. Stories sell. Emotion closes.
Listing features informs people.
Stories help them see themselves using it.

3️⃣ Every word should connect to the customer’s problem.
Your product isn’t the hero.
Your customer is.

4️⃣ Good copy pulls, it doesn’t push.
Curiosity is one of the most powerful marketing tools.
Make people want to keep reading.

5️⃣ Your CTA should feel like a reward.
Instead of: “Submit form.”
Try: “Get your free strategy.”

6️⃣ People don’t read ads.
They read what interests them.
Your job is to make the message about them.

There are also proven frameworks that simplify writing:

• AIDA – Attention → Interest → Desire → Action
• PAS – Problem → Agitate → Solution
• FAB – Features → Advantages → Benefits
• 4Cs – Clear, Concise, Compelling, Credible

You don’t need to reinvent marketing.

You just need to understand how people think and decide.

Because the best copy doesn’t feel like marketing.

It feels like someone finally understood your problem.

👉 Which copywriting framework do you use most often?

Most people treat Claude like a writing partner.

I’ve started treating it like a proposal team.

Once Gamma is connected, you can build full presentations without leaving the conversation.

Here’s the flow I’m running:
• connect Gamma
• connect Gmail
• connect Notion

Then prompt:

“Pull the discovery call. Grab the project brief. Create a campaign proposal.”

Claude finds the context.

Gamma outputs the deck.

Budget, milestones, deliverables. All there.

If I refine the strategy in chat, the slides will evolve as well.

No copy-pasting.
No version chaos.
No losing momentum between idea and output.

One more thing that makes a big difference:

Set up your brand style in Gamma and tell Claude to use it.

Now, everything generated is already client-ready.

This is what AI should feel like.
You think, it builds.

Give Gamma a spin inside Claude. 

https://lnkd.in/eUJ-Skh3

Brand partnership • Top Ecommerce Email Marketer | $200M+ Generated via Email

How to turn emails into client decks

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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taplio

The Battle

Chase Dimond

Marcos Rivera

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Engagements

Likes

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);}Chase Dimond's LinkedIn Performance

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