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

Working with smart people is great.
But it is not enough.

Because intelligence can solve problems.
But humility and kindness build cultures where problems don’t have to exist in the first place.

Here’s why it matters so much 👇

Kind and humble people:

They make collaboration effortless.
You don’t waste energy defending ideas or egos. 
You build together - faster, cleaner, and with more trust.

They create psychological safety.
When people feel respected, they speak up, share bold ideas, 
and admit mistakes early. 
That’s how teams innovate and grow.

They inspire long-term loyalty.
People don’t leave companies - they leave toxic dynamics. 
Working with grounded, genuine teammates keeps great talent around.

 Ways to practice kindness and humility at work:

Listen more than you talk.
You don’t need to have the loudest voice to have the strongest impact. 
Listening builds connection and earns respect.

Give credit - generously.
Acknowledging others’ work doesn’t diminish your own. 
It multiplies the trust and energy in your team.

Keep learning.
The moment you think you’ve “arrived,” you stop growing. 
Stay curious, stay open, and never let success make you unapproachable.

Kind people build strong teams.
Strong teams create big results.

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

If your job costs you your peace,
it’s too expensive.

You deserve a job that lets you sleep peacefully at night -
not one that keeps you awake questioning your worth, your future, or your sanity.

A healthy career doesn’t rely on:

 ❌ burnout
 ❌ constant anxiety
 ❌ toxic expectations

A healthy career is built on:

 ✔️ clear boundaries
 ✔️ supportive leadership
 ✔️ meaningful work
 ✔️ respect for your time and well-being

Your job should challenge you - not drain you.

It should grow you - not break you.

And it should fit into your life, not become your life.

If your work steals your peace, it’s costing you more than it pays.

Funny how your brain has unlimited energy
for worst-case scenarios.

It can write entire disaster scripts at 3 a.m.
With dialogue.
With consequences.
With a soundtrack.

But ask it to imagine things going well
and suddenly it needs evidence, references, and a peer review.

That’s not intuition.
That’s anxiety pretending to be preparation.

You don’t need to stop overthinking.
You just need to stop letting it bully you into pessimism only.

If your mind insists on spiraling,
at least make it spiral in both directions.

Same brain.
Different hypothesis.

Image credit: bywiseword

Reality:
A small, ordinary action.

LinkedIn:
A “high-impact initiative” with “key learnings” and “next steps.”

Clear communication beats inflated language.
Strong professionals don’t need to oversell normal work.

Say what you did.
Say why it mattered.
Move on.

Clarity builds trust faster than buzzwords.

Image credit: TheSecretAcct on Twitter/X

It’s not about collecting business cards or follower counts.

It’s about building bridges with people who get it - who challenge you, inspire you, and open doors you didn’t know existed.

The right network doesn’t just grow your career - it expands your mindset, your confidence, and your opportunities.

Here are 12 ways to build powerful, authentic connections:

1️⃣ Lead with curiosity. Ask, don’t pitch. People love being seen and heard.

2️⃣ Add value first. Share insights, introductions, or encouragement before asking for anything.

3️⃣ Show up consistently. Comment, engage, and participate where your industry hangs out.

4️⃣ Find your communities. Join professional groups, Slack channels, or niche forums.

5️⃣ Attend events strategically. Go where your next mentor, collaborator, or client might actually be.

6️⃣ Follow up. A short, thoughtful message can turn a conversation into a relationship.

7️⃣ Be generous with your expertise. Give more than you take - it builds reputation fast.

8️⃣ Don’t chase status. The best opportunities often come from peers, not big titles.

9️⃣ Stay authentic. Pretending to be someone you’re not is the fastest way to disconnect.

1️⃣0️⃣ Keep it human. Share stories, not sales pitches.

1️⃣1️⃣ Support others publicly. Celebrate others’ wins - it builds goodwill that lasts.

1️⃣2️⃣ Play the long game. Relationships compound like interest; nurture them with time.

The truth? You’re one conversation away from a completely different path.

Image credit: Tim Stoddart

The advice I wish I could’ve given myself 8 years ago:

Create a culture people never want to leave.

Yes, you can’t keep everyone with a 0% turnover rate. 
Let’s face it.

But what you can do is build an environment people don’t want to walk away from.

Build a culture that makes employees:

↳ Recommend it to their friends as the dream job, 
↳ Stay, even if the paycheck isn't perfect yet, 
↳ Come back when the conditions are right.

Think about it:

👉 A competitive paycheck might keep someone for a while, 
But a toxic culture will drive them away for good.

👉 You can offer all the perks, but if the culture is unhealthy, 
Nothing will make your best people stick around.

People stay where they feel valued.

It’s not just about the money—it’s about creating a workplace 
that makes people excited to show up every day.

♻️ Share this post with your network if you agree. 

 Credit: Victoria Repa ( go follow her )

Small habit.
Big impact.

The way you speak to yourself
every morning
becomes your baseline.

Speak growth.
Speak calm.
Speak possibility.

It adds up.

Image credit: Wordofwise_ on Twitter/X

“Hire the people that…”

Interesting how the list skips:
– constant availability
– performative hustle
– being the loudest voice
– working 24/7 for optics

Great teams grow from maturity, not heroics.
From people who communicate clearly, take ownership, and move in sync.

Ego slows teams down.
Trust speeds them up.
Psychological safety keeps the work moving.

Hire for reliability and collaboration first.
Everything else gets easier after that.

“It wasn’t a waste of time if you learned something.”

That’s easy to agree with in theory.
Harder when the lesson came with lost money, bruised confidence, or a year you won’t get back.

Still - experience has a way of paying later.

It sharpens your instincts.
It changes what you tolerate.
It shortens the gap between seeing a red flag and acting on it.

Not every chapter produces visible wins.
Some exist to quietly upgrade your judgment.

And that upgrade shows up in every decision after.

Nobody talks about this part enough.

You can do it tired.
You can do it frustrated.
You can do it unsure.

You just can’t do it if you quit.

Keep going.


Image credit: Dearme2_ on Twitter/X

Here’s a hard truth most people avoid:

If you’re not making mistakes, you’re not moving forward.

I learned this the slow way.

Early on, I tried to get everything right.
Perfect plan.
Perfect timing.
Perfect execution.

And progress?
Basically stalled.

Things only changed when I gave myself permission to be wrong.

To test ideas that might flop.
To ship work that wasn’t perfect.
To learn out loud instead of waiting in silence.

Mistakes aren’t failure.
They’re feedback.

The people doing the most interesting work
aren’t avoiding mistakes.

They’re just willing to make them faster.

Safe paths feel good.
But they don’t teach much.

Growth always comes with friction.
That’s the price of trying something new.

Image credit: Tomas Gorny

Marketing is great they said…


P.S. If you write emails and you’re looking for inspiration, check out:

inboox.ai

10 years of rejection.

That's how long Squid Game's creator spent pitching his script.

Studio after studio said no.
Too dark. Too violent. Won't work.

Then Netflix took a chance.

28 days later, it became their most-watched show in history.

A decade of "no" turned into a $900M yes.

Most people quit after a few rejections.
They assume the silence means the idea is bad.

But rejection isn't a verdict.
It's just timing.

The right opportunity doesn't always show up first.
Sometimes it shows up tenth. Or hundredth.

If you're getting rejected right now, consider this:

You might not be wrong.
You might just be early.

Keep going.


Image Credit: Amy Sussman/WireImage; Noh Juhan/Netflix

How to survive marketing in 2026.

Open your laptop.
Check Slack.
Three notifications in…

…and you already feel behind.

Sound familiar?

In 2026, “digital marketer” doesn’t mean one role anymore.
It means the entire agency in one tab.

Copywriter.
Strategist.
Videographer.
Social media manager.
Designer.
Editor.
Analyst.

All before lunch.

From experience, the problem isn’t a lack of skill.
It’s the expectation that one person can do everything at once and do it well.

Burnout doesn’t come from hard work.
It comes from an impossible scope.

The marketers who survive aren’t the busiest.
They’re the ones who set boundaries, prioritize ruthlessly, and stop trying to be great at everything every day.

Because marketing isn’t about doing more.
It’s about doing the right things consistently.

Agree?

Most marketers track a ton of metrics.

Very few know which ones actually matter.

Here are 7 worth paying attention to, plus how to improve each one:

(bookmark this)

Our email domains kept getting blacklisted at my agency.

Everyone assumed we were sending too aggressively.

After diving into the data, we found the real issue.

18% bounce rate.
From a "verified" list.

We had bad data.

𝗧𝗵𝗲 𝗵𝗶𝗱𝗱𝗲𝗻 𝗰𝗼𝘀𝘁𝘀 𝗻𝗼𝗯𝗼𝗱𝘆 𝘁𝗮𝗹𝗸𝘀 𝗮𝗯𝗼𝘂𝘁:

Deals lost during 2-3 weeks of rebuilding.
Hours spent verifying and cleaning lists.
Teams questioning their skills when it's not their fault.
Buying new domains every month.

We thought this was just how outbound worked.

Then I saw a friend's company sending thousands of emails each week.
Same domains. Month after month.
Strong deliverability maintained.

They were using Prospeo.io's data.

SMTP handshakes verify emails before you send.
BounceBan removes risky addresses automatically.
Weekly updates catch job changes that kill domains.

After testing several providers, Prospeo consistently delivered the cleanest data.

Our domains have been going steady for months now.
Data prep time cut by 80%.
Bounce rates dropped from 18% to under 2%.

Clean data isn't just about deliverability.
It's about keeping your team confident and productive.

What hidden costs is bad data creating at your agency?

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

6 Copywriting Techniques You Can Leverage for Your Sales Pages:

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January hits different for ecommerce founders.

Sales slow down. Costs don't.

You're staring at:
- Depleted inventory
- Q1 expenses stacking up
- Ad costs that won't wait
- Cash tied up in last quarter's orders

The revenue will come. But the bills are here now.

This is the ecommerce cash flow trap.

Most founders either:
→ Wait it out and lose momentum
→ Take on debt with rigid terms
→ Give up equity way too early

That's where Wayflyer comes in.

Capital in 24-48 hours. Non-dilutive. Flexible repayment based on your actual sales.

No giving up ownership. No waiting weeks for bank approvals.

You restock. You scale Q1 ads. You keep the momentum going.

$6B+ already deployed to brands like yours.

If your cash flow is playing catch-up, get your offer today: 

https://lnkd.in/gJsgPrrm


#WayflyerSponsor

I used to think GTM complexity was just part of the job.

Multiple tools. Manual handoffs. Workflows that took hours to build and days to fix.

Last week I tested Apollo's AI Assistant on something different: workflow creation.

Instead of clicking through menus and configuring triggers manually, I just described what I wanted in plain English.

The AI built the multi-step workflow in minutes.

What used to require:
→ A GTM engineer
→ Multiple tools stitched together
→ Hours of setup and testing

Now happens in a single conversation.

Same thing with building prospect lists, creating sequences, or analyzing campaign performance. Describe what you need. The AI handles the execution.

Most teams are still doing GTM the old way. Clicking through settings, connecting triggers, testing each step manually.

Meanwhile, the fastest operators are just talking to the AI.

GTM shouldn't require an engineering degree.
It should require clear thinking and the right tools.

Join the beta waitlist:

https://lnkd.in/gW2ZeEUb

#ApolloAIAssistant #ApolloPartner

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?

Most pricing consultancies hire from McKinsey or Simon-Kucher.
We hired Emily Sanz from American Airlines and British Airways.

When I was building out the Pricing I/O team, I had a choice. 
I could hire the typical profile: ex-consultants who'd spent their careers making slide decks about pricing but never actually owned a P&L.

Or I could find people who'd lived pricing in industries that do it better than almost anyone.

Emily had spent years in airline pricing. The joint business between them. 
She'd done consumer pricing, B2B pricing, and everything in between.

Airlines invented revenue management. 
They've been optimizing for 50+ years. 

They deal with infinite data points, razor-thin margins, and customers who compare prices obsessively. If you can do pricing there, you can do it anywhere.

What Emily brought to Pricing I/O that we couldn't have gotten from a traditional consultant:

→ An obsession with customer segmentation. 
Airlines don't have "3 tiers." They have hundreds of price points for the same seat, because different customers have different willingness to pay.

→ The concept of "quality of revenue." 
Not just how much you closed, but what kind of revenue it is. A discounted seat to fill the plane is not the same as a full-fare business traveler. Same applies to SaaS.

→ A data-first mindset. 
In aviation, you don't guess. You measure, test, and iterate constantly.

When she joined back in 2023, I asked her what surprised her most about SaaS pricing.

Her answer was about how little data most companies actually use. 
They have it. They just don't look at it.

We don't hire career consultants who've never operated.
We hire people who've lived pricing in industries that do it better than anyone, and bring those lessons to SaaS.

That's how we work in the trenches differently.

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

Four years ago, it was just me and a laptop.
This room held 25 people last meeting.

We gathered the Pricing I/O team for our end-of-year off-site, and something hit me during the planning session.

We're not just growing. 
We're building something that compounds.

→ 30% revenue growth year over year.
→ Pipeline doubled since Ali joined in Q3.
→ Client satisfaction scores hitting 10 out of 10.

But here's what really gets me: the debates in that room.

Some of them going back and forth on engagement models. Others challenging assumptions. 

The whole team leaning into problems that didn't exist when we were a team of four.

I used to think scaling a consulting firm meant losing the magic.
Turns out, with the right people, the magic multiplies.

2026 is going to be even better. 

We're cooking up something new, can't share details yet, but let's just say it involves working code and a launch window in Q1/Q2.

Stay tuned.

The best hires don't just check boxes, they make you rethink what the boxes should be.

Lauren DeGirolamo, MBA, CPP joined us as a Pricing Strategist back in December.

Before Pricing I/O, she was Director of Strategic Pricing at Baker Distributing, leading a team of 9. Before that, she spent nearly three years at Resideo navigating pricing through supply chain chaos.

One thing from her background that stuck with me: she restructured a pricing matrix from over 1,400 customer conditions down to 7.

That's not optimization. That's the kind of simplify-the-complex thinking that separates good pricing people from great ones.

When I asked her what surprised her most about joining us, she didn't mention the work or the clients.

She mentioned our offsite.
"This was the first time I had ever seen a CEO involving his entire team in high-level strategic decisions, listening with open ears to hear all perspectives."

That one got me.

Because that's exactly the culture we're building. 
Not top-down mandates. Real debate. Real input. Real ownership.

Lauren called it "the secret weapon behind Pricing I/O's success."
I'd have to agree.

Her spiciest pricing take?
"Lowering prices too much can actually hurt market share, it signals to enterprise buyers that your product is less capable."

Strong opinions backed by experience. That's what we look for.

Oh, and her karaoke song is "Remember the Name" by Fort Minor. 
If you know, you know.

Welcome to the team, Lauren. 
Love seeing you win already.

25 people. $10M bootstrapped. Zero outside funding.
And the culture is the best I've ever been a part of.

I'm not saying this to brag. 
I'm saying it because it almost didn't happen this way.

The original plan was me, myself, and I.

But here's what I've learned building Pricing I/O:
The company you build reflects the problems you solve.

We help companies capture value. 
So we had to build a company that captures its own value, through people, not just process.

We teach teams to own pricing long-term. 
So we had to build a team that owns their work, not just executes tasks.

We work in the trenches with clients. 
So we had to hire people who want to get their hands dirty, not just advise from a distance.

Every value we preach to clients, we had to live internally first.

That's what makes the culture real. It's not a poster on a wall. 
It's the business model.

We're still figuring it out. Still learning. Still making mistakes.

But building in public means being honest about the journey, not just the wins.

Clio scaled from 250 to 1,000+ employees.
Their pricing strategy? "Sporadic" and "on a needs basis."

Here's the thing most people miss about hyper-growth: 
the faster you scale, the more your pricing cracks show.

When we started working with Clio, they had a cultural resistance to monetization. 

The team genuinely wanted to deliver "outsized value" to customers, which sounds noble until you realize it was capping their ability to reinvest in the very innovation customers were asking for.

So we ran a full revision of all their products and service offerings.

The foundation? Their own "law firm maturity model", a blueprint that let us design pricing and packaging that grows alongside their customers, not against them.

The results hit across the board: NRR improved. ARPA improved. LTV improved.

But here's what changed the game long-term:
Pricing is now part of every single new product launch and release at Clio.

Not an afterthought. Not a "we'll figure it out later." A strategic lever from day one.
That's the shift. 

→ From reactive to proactive. 
→ From sporadic to systematic.

And it doesn't happen by accident, it happens when you treat pricing like the growth engine it actually is.

Me and Min S. FitzGerald talked about it on my podcast.
You can watch the full episode on Pricing IO Youtube channel.

Most pricing projects start with excitement and end with a deck nobody opens.
I've seen it happen dozens of times.

Great research. 
Solid recommendations. 
And then... nothing changes.

Why?

Sometimes it's because nobody owned the implementation.
Sometimes it's because the company wasn't ready, they didn't have a clear product strategy, and pricing can't fix that.

But when the foundation is solid, and you have a partner who works in the trenches with your team?

That's when pricing goes from "expense" to "investment."
Swipe through for what actually works, and what doesn't.

Failure

How long does it take your company to launch a new pricing model?

If the answer is "we'd need to check with engineering" or "probably a quarter," you have an infrastructure problem.

Most billing systems were architected when pricing was three simple tiers and annual contracts. 

Adding each new capability felt manageable, usage tracking here, credits there, custom packages for enterprise.

But step back and look at what you've built right now. It's infrastructure. 
Complex, mission-critical infrastructure that nobody planned for.

Now there's a gap opening up. 
Some companies can test new pricing in days. 
Others need months for basic changes.

Some can close deals with flexible packages. 
Others lose deals because their system literally can't support what the customer needs.

That gap isn't about engineering talent. 
It's about whether your monetization infrastructure was designed for the world we're in now or the world we left behind.

Tomorrow, Manish Choudhary from Flexprice and I are walking through how this shift happened, why it caught everyone off guard, and what separates companies that can move fast from companies that are stuck.

How Monetization Became Infrastructure and No One Noticed
January 15, 10:00 AM EST
Register here ↓
https://skd.so/LBzBi3

Vibe coding is going to kill more B2B SaaS companies than AI competition will.
Here's why ↓

Right now, there are CEOs downgrading every SaaS subscription to the cheapest tier, and building custom tools on top with Lovable, Bolt, and Claude.

The CRM becomes "just a dumb database."
The premium analytics features? Vibe-coded in an afternoon.
The RevOps workflows you charge extra for? Replaced by something stitched together over a weekend.

The implication for pricing is massive:
Differentiation that used to last 5-6 years in client-server days... then 1-2 years in SaaS... now lasts weeks or days.

When your customer can vibe-code a "good enough" version of your premium features themselves, your pricing power evaporates.

So what becomes the moat?
Two things:
→ Distribution (can they find you before they build it themselves?)
→ Depth of integration (are you so embedded they can't rip you out?)
→ Data (do you have proprietary data they can't replicate?)

If your pricing strategy assumes feature differentiation will protect you, you're already behind.

The companies that win will price for outcomes and depth of integration, not feature access.

Because features are getting commoditized faster than anyone predicted.
How are you thinking about this in your pricing model?

Credit-based pricing is an admission that you don't understand your value yet. 
I've been watching the AI pricing space closely, and here's what I'm seeing across dozens of companies ↓

They're adopting credits and tokens not because it's the best model, but because they're uncertain about two things:
→ What use cases will actually drive adoption
→ What value those use cases deliver

So they default to tracking costs (tokens, compute, API calls) instead of outcomes. 
And here's the thing, that's not necessarily wrong at this stage.

But there's an important distinction to make here.

Cost-plus credits tied to tokens or compute? 
That's transitional. 

When you're genuinely uncertain about value delivery, it buys you runway to learn. 
But it shouldn't be a destination.

Action-oriented credits tied to meaningful outcomes? 
That's different. 

Companies like Clay AI and HubSpot have built successful credit systems because the credits correlate to actions that derive value, updating a contact, enriching a record, taking a step that moves the business forward. 

Easy to understand, easy to connect to ROI.

The difference is whether credits measure what you spend or what the customer gains.

Three questions to ask yourself if you're running credits today:
1/ Are you tracking which actions correlate with customer success?
2/ Do you know which use cases drive the most willingness to pay?
3/ Do your credits reflect cost consumption or value delivered?

If your credits are just a proxy for compute, you're not pricing strategically, you're billing for infrastructure.

What's your take, are your credits measuring cost or value?

AI companies can capture more value than SaaS ever could.
Here's why ↓

On-premise software captured roughly 5% of the value it created. 
You were paying for access, that's it.

SaaS changed the game. 
Suddenly you could track activity, usage, outcomes. 
Value capture jumped to 10-15%.

AI changes it again. 
Usage patterns vary wildly. 
One customer might use 10x what another does, and get 10x the value.

The companies figuring this out are capturing far more than the old SaaS playbook allowed.

But here's what most are getting wrong:
They're still pricing AI like it's SaaS. Flat seats. Fixed tiers. One-size-fits-all.

That made sense when usage was predictable. It doesn't when one user generates 50 API calls and another generates 5,000.

The shift isn't just about pricing models. It's about how you think about value exchange entirely.

Your CFO now needs data science skills to understand AI unit economics. Performance margins can swing from 10% to 75% depending on which model you're running.

This is a different game with different rules.
Are you still playing by the old ones?

You're not going to lose your customers if you raise your prices.
I know. It doesn't feel that way.

I've heard this from hundreds of founders and CEOs. 
Smart people. Running great companies. 
Paralyzed by the thought that one pricing change will undo everything they've built.

Here's what actually happens:
We help them build the case. 
Research. Data. Competitive benchmarks. 
They see the evidence that they're underpriced.

Then comes the hard part: actually telling customers.
They start with a few. Hold their breath. Wait for the backlash.

And most of the time?
Customers say yes.

Not all of them. But enough. 
And suddenly the fear dissolves. 

They realize they were leaving money on the table for years because of a story they told themselves.

Here's what we've learned from 400+ engagements:
We almost never recommend lowering prices across the board.

What we find is companies are underpriced in segments they didn't realize, while over-discounting in others.

The problem isn't usually "we charge too much."
It's "we're not charging for the right things, to the right people, in the right way."

If you've been putting off a price increase because you're scared of the reaction, you're not alone.

But the fear is almost always bigger than the reality.

Nobody wakes up thinking "today's the day I fix pricing."
But by the time pricing feels urgent, you've already paid the price.

It usually gets pushed. Delayed. Deprioritized.

There's always something more urgent, a product launch, a reorg, a board deck due Friday.
Meanwhile, the warning signs pile up quietly.

Your best rep starts discounting 30% "just to stay competitive." Finance notices tier 1 is overflowing while tiers 2 and 3 collect dust. A prospect tells you "you're too expensive", then signs with a competitor charging 40% more.

Each one feels manageable in isolation.

But together? They're symptoms of pricing that stopped reflecting your value a long time ago.
The hardest part isn't the fix. 

It's admitting you've been leaving money on the table while focused on everything else.

I've seen this exact pattern in hundreds of companies. 

If you want to win it, start by recognizing the early signals and acting before the damage compounds quarter over quarter.

How many of these signals are showing up at your company right now?

$300K to $30M ARR in two and a half years.
100x growth.

One change: the pricing metric.

The product was a dispatching tool for insurance companies. Seat-based pricing.

Here's the problem, the better we performed, the less revenue we got.

Customers optimized routes, needed fewer seats, and downsized at renewal.
We were penalizing ourselves for delivering value.

So we tested five or six different metrics. Ran correlations. Talked to customers.

Per claim made the most sense.

It aligned with how insurance companies already tracked value and cost. 

Claims scaled with their business. Our revenue finally moved with theirs.

That's when I realized: pricing isn't a math problem. It's a value alignment problem.

The metric you choose determines whether you grow with your customers, or get left behind.

If you're adding AI to your SaaS product, you're about to face a pricing decision that most companies get wrong.

Do you charge per seat? Per usage? Per outcome? Some combination?

The answer depends on how you layer your pricing model. And there are really only three layers to work with.

Base 
Your platform, features, functionality. What customers get access to regardless of how much they use.

Allowance 
What's included before overage kicks in. This is where most companies mess up. Too little creates friction before customers see value. Too much kills your expansion revenue.

Meter 
The unit you charge for when they scale. Get this wrong and customers game the system. Get it right and revenue grows with their success.

Every hybrid pricing model is just a different combination of these three layers.

Access Tiers? Just Base. 
Platform fee plus usage? Base + Meter. 
Credits with overage? All three layers working together.

I broke down five models we see working in the market right now, with specific examples like Intercom Fin's $0.99/resolution and when each model fits best.

Here's what I've learned after 400+ pricing engagements: the model you pick matters less than whether it matches how your customers actually buy and scale.

Most companies copy competitors. 
The ones that win design for their own customer journey.
Which model fits how your customers grow?

Labeling something as "AI" actually lowers trust.
I know. It sounds backwards.

Every company is racing to slap "AI-powered" on their product. 
The assumption is it increases perceived value.

The data says otherwise.
In willingness-to-pay research, the AI label barely moves the needle on what customers will pay. And in some cases, it actively creates skepticism.

Why?
Because the market is shifting from "play AI" to "may I", as in, "may I see proof this actually works?"

Early adopters bought the hype. 
The next wave of buyers wants evidence.

ClickUp figured this out. 
Their standard plan is $7. Their AI plan is $28, 4x the price.

But they didn't just slap "AI" on it and hope for the best.
Their positioning: "This replaces 4-5 other AI tools you're already paying for."

The value prop isn't "we have AI." 
It's "we simplify and centralize what you're already doing across multiple tools."

Simplification + consolidation = worth the premium.

The companies winning at AI pricing aren't selling AI. They're selling outcomes that happen to be powered by AI.

What are you actually selling?

If your sales team doesn't believe your solution is worth the price, they won't sell it.

They'll discount it. They'll apologize for it. They'll position it as "a bit expensive, but..."

I had a client where the salesperson literally felt bad charging customers. 
Not because the product was bad. Because SHE didn't believe it was worth what they were asking.

That feeling? It bleeds into every demo, every negotiation, every close.

You can have the perfect pricing model. The perfect packaging. The perfect positioning.

But if your own team doesn't buy what they're selling, your customers sure as hell won't.

The problem isn't your price. 
It's that you never convinced your team of the value first.

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Pragmatic Marketing, Product Management Certification Level 4

Invited as guest lecturer for lab to market capstone courses to speak on topics of product management, general management, and technology trends

I managed to work my way through all four years of college while achieving Provost honors.

Warren College - Minored in Japanese Language and Studies.

Hi, I'm Marcos Rivera

•  I have 25+ years of pricing expertise in Tech
•  I was the Head of Pricing for Vista Equity Partners
•  I have helped price 400 products...and counting​
•  I teach pricing confidence from MBA students to world-class CEOs
•  I am an award-winning author, speaker, investor, and entrepreneur

Here's My Story in a Nutshell

I was raised by a single mother in a one-bedroom apartment in the Bronx. The streets were hard on me, but I survived by applying what my mom taught me:  Stay curious, take the lead, and give help.

Fast forward to today, Software as a Service has transformed almost every business, from music to marketing to medicine. I learned a lot straddling dual roles as a product executive and pricing expert my entire career, but my AHA moment came to me after noticing an unwavering pattern:

Most B2B SaaS leaders spend time building value but not enough time capturing it!

So in the spirit of staying curious, I discovered that many B2B SaaS leaders see pricing as a "black box"; they guess, fumble, and wing it most of the time.  They needed help!

From there, I decided to take the lead and help B2B SaaS businesses by dedicating a practice that teaches them step-by-step directions for monetizing value and unlocking growth.

And this is where our story begins. Join us and take control of your most powerful growth lever - Pricing.  It would be my honor to help you! Send me a DM or head to our website: www.pricingio.com

You can also order my debut book, Street Pricing: A Pricing Playlist for Hip Leaders in B2B SaaS (link in bio)

Go capture that value!

Marcos

For this benchmark report, PricingSaaS has examined over 400 B2B SaaS companies across 10 different categories to uncover AI monetization strategies, usage based pricing metrics and created a recap of changes in Q1 of 2024.

We hope you find it helpful and insightful.

2024 B2B SaaS Pricing Q1 Benchmarks & Models

Pricing I/O is a training and coaching boutique helping high-growth B2B SaaS companies accelerate ARR growth and market share. We unlock growth by taking a simple, powerful, and easy to understand approach to monetization – we call this approach the 5Q Pricing Framework.

Pricing I/O: Your B2B SaaS Pricing Experts

25 years of pricing. 500+ SaaS companies.
One conversation where I held nothing back.

Rohit asked me the questions most people are afraid to ask:
→ What's the single biggest pricing mistake you see repeated?
→ How do you know if it's a pricing problem or something else?
→ Should AI features be bundled or priced separately?
→ What made you change your mind on pricing cadence?

I shared the 100x growth story I don't tell often.

Admitted where I got it wrong.

And broke down how to actually think about pricing AI, not the theory, the real decisions.

If you've got 35 minutes, this one's worth it.

Watch the full episode of The AI Pricing Podcast ↓
https://skd.so/OCIaV6

Most SaaS companies treat usage limits as technical guardrails.
Big mistake.

They’re your upgrade engine.

Data retention windows. 
Source limits. 
Processing hours. 

These aren’t just product constraints, they’re monetization strategy.

The key: Set limits where customers naturally hit them as they get MORE value. Not where they get frustrated.

When customers hit limits, they’re succeeding. That’s when they upgrade.

Here’s what that looks like:
→ Starter: 3 sources, 30-day retention
→ Pro: 10 sources, 90-day retention
→ Enterprise: Unlimited, 1 year+

That structure creates a $47K ARR expansion path per customer.
These should feel like growth milestones, not arbitrary restrictions.

What usage limit is driving the most upgrades in your model?

Should you charge for AI separately or bake it into the product?
I get this question constantly. 

And the honest answer is: it depends on what your AI actually does.

I've seen companies destroy expansion revenue by giving AI away for free when they should have charged. 

I've also seen companies kill adoption by charging separately for AI that should have been invisible.

The mistake is thinking there's one right answer. There isn't.

After working through this with dozens of companies, from $10M ARR startups to PE-backed portfolio companies, I keep coming back to three distinct approaches.

The first works when AI enhances the existing experience. 
Makes things faster, smarter, better, but the job-to-be-done is the same. 

Think autocomplete, smart suggestions. 
In this case, don't charge separately. 
Bake it in and raise prices across all plans.

The second works when AI unlocks adjacent use cases. 
Same user, but now they can do something they couldn't before. 
This is your premium tier or add-on play.

The third works when AI creates entirely new users or workflows. 
Different audience, different product. 

This needs its own identity, maybe bundled, maybe standalone.

The question isn't "should we charge for AI?" It's "where does AI create value, and for whom?"

Which of these three describes your AI?

Your packaging model isn't broken because it's "wrong."
It's broken because you outgrew it.

Here are 5 signals I see when companies need to evolve their packaging:

1. Sales is discounting on every deal to "make it fit."

When your tiers don't match how customers buy, reps start hacking. Custom bundles. Creative discounting. Anything to close.

That's not a sales problem. It's a packaging problem.

2. Customers cluster in one tier while others sit empty.
If 80% of customers are in your middle tier and the other two barely move, your packaging isn't giving them a reason to choose.

3. You're building features no one's paying for.
Product ships something great. It gets buried in "Enterprise." No one upgrades for it.

That's a signal the feature deserves its own packaging conversation.

4. Expansion revenue is flat even though usage is up.
Customers are using more. Getting more value. But NRR isn't moving.

Your model isn't capturing the growth happening inside accounts

5. The pricing conversation dominates every sales call.
When customers spend more time asking "what's included where?" than talking about their problems, packaging is creating friction, not reducing it.

None of these mean you picked the wrong model.
They mean your business evolved and your packaging didn't keep up.

Here's the thing about packaging: it's not a one-time decision.

Companies that treat it like infrastructure instead of a living system end up stuck, either too rigid to capture value or too complex to sell efficiently.

The best packaging matches your stage. 
And as you grow, it should grow too.

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