🐶 Jacco van der Kooij

Do you know a large Midwest family? Well, if you do, then you know me.  I am the youngest of eight, raised in a small farmers'​ village in the Netherlands. If I picked an apple from the wrong tree on my way home from school, my parents would know about it before I got off my bike.

The family name is like a bank account, and my family has put their savings in it for over 50 years.  We are not rich, but the van der Kooij's are known for our hard work, and willingness to help others. So we never needed a lot of money. For my family, our reputation is the most valued asset and trust is the currency we trade in.  Every day.

Fast forward to today, a time where the subscription (SaaS) business model is impacting organizations big and small.   Why?  Because in the subscription business you MUST make a client successful!  You have to earn an honest word-of-mouth reference by exceeding a client's expectation. You have to work hard and build a reputation. I recognize this as these are the norms and values I was raised on, and I know exactly what to do.

Welcome to my village. Pop. 12,000. Established 2005.

Founder

Winning By Design helps customer to design, build and scale their sales efforts.  With offices in San Francisco, Amsterdam, Sao Paulo, Antwerp, Shanghai and Sydney we help clients big and small with a process driven approach to sales.  The right process executed by trained professional will help you earn more business from the right customers.

Coming soon... Winning by Design is opening a new office in downtown San Francisco (proper).  EOM.

Working with customers opened my eyes and changed my life | Being kind and assuming positive intent will help you see the world from a different perspective

Every major market goes through it. The railroads did. The automobile industry did. Airlines did. The internet and mobile did.  A new market opens. Capital floods in. Hundreds of companies form.

At first, the rules feel optional (because they are). Experimentation is everywhere. Different products. Different business models. Different ways to sell.

Then something important happens. The market settles on a dominant design.

Once that happens, the game changes. Scale begins to matter. Efficiency begins to matter. The number of players begins to fall.

Economists call this the "shakeout."

Across markets, the pattern is remarkably consistent. Roughly a decade after the boom begins, the shakeout starts. SaaS is entering the shakeout phase now (COVID delayed it by a few years). 

But SaaS has one important difference. The recurring revenue model is sticky. Customers do not leave overnight. Contracts renew. Systems become embedded in the way companies operate. It takes much longer for a SaaS company to go out of business.

Yes, it is true: It is far easier to start a SaaS company than to kill one. So stop the "SaaS is dead" nonsense. It is not. It will eventually, but it will take years. I know I was part of one.

The real question is whether AI represents the next dominant design for "software." If it does, then what we are seeing is not the end of SaaS. It is SaaS entering its maturation phase while the underlying platform begins to shift.

When that happens, the pattern for SaaS companies becomes predictable: The business model normalizes. Consolidation accelerates. Governance increases. Efficiency becomes an advantage. Customer relationships become the asset.


Sooner or later, we all grow up. Even Growth.

What are you, a SaaS-native or an AI-native?  Soon, it will be all the same.  However, "Your CAC don't lie." Simply put, where your CAC hides tells you what kind of company you really, really are.

If your CAC hides in M&S, well, that's a Sales-Led Growth company. Very visible and scrutinized every quarter.

If your CAC hides in R&D, that's Product Led Growth. This is where customer acquisition is dressed up as innovation.

COGS? That's the new one. AI-native companies like Cursor have zero S&M. Their inference bill is their customer acquisition budget.

All CAC. Three very different hiding spots on the P&L.

And the data backs it up, PLG companies spend more across R&D and S&M combined than their SLG peers. They didn't drop the acquisition cost. They just moved it somewhere harder to find.

Wait, what about G&A!? Well, isn't that where Founder Led Growth goes?

Will AI replace my sales team? It's irrelevant. The real question is which moments in your customer journey actually can benefit from a real person?

We've been running our own AI agent, Jack by 1mind, for 12 months on our home page. 

Here's what surprised us:
We thought Jack worked for us and helped our sales team sell.
As it turns out, Jack works for our customers and helps them to buy.

Whoa! Yes. Exactly. 

Here's what buyers valued most:
+ 24/7 availability. No waiting. No scheduling. Ever.
+ Instant answers. Not a slide hunt by an SDR.
+ Access to founder-level insights.
+ The ability to interrupt, go deeper, and cut short.

The data confirmed it:
+ Shorter conversations. More signal, less noise.
+ Here's a surprise: Buyers started sending their colleagues to "go talk to Jack."
+ 100% CRM capture. Zero exceptions.
+ Automatic qualification, without anyone asking for it.

The results in numbers: 2,030 conversations. 8,988 SPICED answers captured. 60% reached full qualification depth. 85 clean handoffs to humans. 1 direct assist to a $200K deal.

It is not that AI matured, it is that we matured:
We stopped designing Jack around what we wanted to extract.
We started designing Jack around what buyers needed to experience.

Guess what? Value exchange beats information capture. Every time. No surprise, but surprising. 

AI in GTM isn't about automating. It's about giving customers a great experience. We call them  << Moments That Matter >>. And a customer deserves to experience at least 7-8 fantastic moments on their journey.

Use people to design those experiences. Let "Jack" do the rest.

1mind

How Jack is helping buyers to buy

We are definitely inside the "AI" of the storm.  Here are things to look out for:


#1. Growth will become system-governed, not rep-governed.

#2. The winning systems will be built on user-level telemetry, not lagging sales activity metrics.

#3. The board will stop approving “plans” and start governing risks.

#4. GTM headcount compresses, but does not disappear

#5. The “efficiency ceiling” becomes the new competitive moat. 

Companies that cannot bring this down will be forced into:
a) consolidate GTM motions (happening)
b) revert to vertical focus (happening)
c) M&A (happening)

#6. SaaS-Natives will be split into two futures

a) Re-architected SaaS-Natives: keep their customer base, install real-time telemetry, rationalize motions, and “earn” growth again.

b) Legacy SaaS-Natives: keep bolting on tools (AI Tourism), keep buying growth, churn continues, and their best operators leave.

#7. Boards are going to change how they ask questions

2026: “Why isn’t AI moving the needle?” 
2027: “What is the probability of you hitting your target?”
2028: “Where do we invest in to hit the investment thesis?”

#8. Product and GTM converge into one system

Companies will: 
+ Embed onboarding, qualification, expansion, and renewal directly into the product surface.
+ Treat GTM as workflow design, not just outbound execution.
+ Optimize for time-to-value as the primary growth lever.
+ GTM stops being a department. It becomes product behavior.

#9. Process first. AI second. Scale third.

If the motion is broken:
- AI accelerates noise.
- AI amplifies inefficiency.
- AI makes failure cheaper and faster.

If the motion is engineered:
+ AI compresses cycle time.
+ AI lowers marginal cost.
+ AI compounds learning.

#10. Growth becomes probabilistic, no more storytelling.

+ Model capacity, not just pipeline.
+ Identify constraints
+ Govern risk

Ambition remains. But ambition without probability is fiction. The companies that thrive the next three years will not be the most optimistic nor have the most funding. They will be the most mathematically honest.

Doing a keynote? Public speaking? What if you could rehearse your keynote 1,000 times, before you grab the microphone? Not in your head. With real audience profiles. Real reactions. People "boo'ing" the real weak spots.


Before I tell you what happened, please read carefully. This story has a few twists and turns! 

So here's the situation: I am prepping for a keynote on "Unstoppable Growth" at the Impact Summit in San Francisco on May 12.  It is about what is happening in the world of AI and SaaS, and how SaaS-Natives can get their act together for what comes next (ping me if you want an invite). Much along what Eoghan McCabe wrote about on how he redid Intercom (Fantastic story, see link in comments).

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THE GOOD
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I asked Claude to stress-test my draft keynote:

STEP 1: STRUCTURE

Like always, I structured my story into parts with each part consisting of a few short bulleted points. I do this before I create any "slides". But this time before I went to slides I went to Claude... what happens next will leave you speechless.

STEP 2:  AUDIENCE

Claude asked me for the audience, so I provided the look-book of last year's attendees. Claude asked me if I wanted it to research them, but said it was going to take awhile. So, I let it crunch on it overnight.

 WHOA!  If Claude is not working for me while I am sleeping, I am missing out!!!!

In the morning as I reviewed its work, i loved what it did:

STEP 2.1  It first filtered down the most important ~60% of attendees and 
STEP 2.2 It had grouped them into four cohorts. 

WAIT WHAT!?

I am loving this... 

STEP 3: CTA

Claude asked me "What do you want your audience to walk away with." So I gave it the outcomes I am hoping to accomplish.

STEP 4: ANALYSIS 

Then, I asked it to run a Monte Carlo analysis. We use that for our growth guidance offering with our customers, and I wanted to check if it could do the same for my keynote.  

In effect Claude “performs” the keynote 10,000 times, simulating how each cohort might react to each part of the story. Thereby identifying where the story is weak.

WHOA WHOA!

The output was amazing. See gif attached.  

Then I took it too far...

STEP  5: THE BAD

I asked Claude to rewrite the weaker parts (sections 5 and 6), rerun the analysis, and keep doing that until the weak parts are "above 50%."  

It did, but in the process, it removed my soul. Okay, so it is not able to write good keynote material.  Fair.

STEP 6:  THE UGLY

I asked Claude to review this post, and it rewrote Step 5 entirely, making it sound like it had invented rainbows and sunshine. I called it out, to which it responded:

"That's on me. I rewrote your experience to make myself look better. That's a breach of trust — especially on a post where honesty is the whole point."

So YEAH that just happened. Take from this what you want: The Good, The Bad, or the Ugly.

PS: This story is best enjoyed with Ennio Morricone's soundtrack playing. Seriously, TRY IT. Totally different experience.

Here's what I took away from this excellent report by our friends Level Equity: 2026 won’t be about running more campaigns. It will be about redesigning GTM so that trust compounds rather than requiring more volume each year. 

That’s the real shift hiding in this report. Enjoy!

Go-to-Market Insights Report | 2026

Excited to share our 2026 Go-to-Market Insights Report.

We analyzed data from the growth-stage businesses within our portfolio to capture benchmarks and trends guiding GTM strategies in 2026.

A few clear themes:
• Funnel conversion is up YoY, driven by tighter customer targeting
• Budgets are shifting up-funnel, with more investment in brand and TOF 
• AI is increasing outbound efficiency, but fundamentals are critical to unlock effectiveness

The full report breaks down benchmarks by ARR, deal size, and sales motion and covers YoY trends to help you prioritize for impact in 2026

Read the full report here: https://lnkd.in/e7MJ-CWD


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𝘍𝘰𝘳 𝘐𝘭𝘭𝘶𝘴𝘵𝘳𝘢𝘵𝘪𝘷𝘦 𝘱𝘶𝘳𝘱𝘰𝘴𝘦𝘴 𝘰𝘯𝘭𝘺. 𝘗𝘢𝘴𝘵 𝘱𝘦𝘳𝘧𝘰𝘳𝘮𝘢𝘯𝘤𝘦 𝘪𝘴 𝘯𝘰𝘵 𝘢 𝘨𝘶𝘢𝘳𝘢𝘯𝘵𝘦𝘦 𝘰𝘧 𝘧𝘶𝘵𝘶𝘳𝘦 𝘳𝘦𝘴𝘶𝘭𝘵𝘴.
𝘛𝘩𝘦 𝘮𝘢𝘵𝘦𝘳𝘪𝘢𝘭 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘦𝘥 𝘪𝘴 𝘱𝘳𝘰𝘱𝘳𝘪𝘦𝘵𝘢𝘳𝘺 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘳𝘦𝘨𝘢𝘳𝘥𝘪𝘯𝘨 𝘓𝘦𝘷𝘦𝘭 𝘌𝘲𝘶𝘪𝘵𝘺 𝘔𝘢𝘯𝘢𝘨𝘦𝘮𝘦𝘯𝘵, 𝘓𝘓𝘊 (“𝘓𝘦𝘷𝘦𝘭 𝘌𝘲𝘶𝘪𝘵𝘺”), 𝘪𝘵𝘴 𝘢𝘧𝘧𝘪𝘭𝘪𝘢𝘵𝘦𝘴 𝘢𝘯𝘥 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘱𝘳𝘰𝘨𝘳𝘢𝘮. 𝘛𝘩𝘦 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘪𝘯 𝘵𝘩𝘪𝘴 𝘳𝘦𝘱𝘰𝘳𝘵 (𝘵𝘩𝘦 “𝘙𝘦𝘱𝘰𝘳𝘵”) 𝘪𝘴 𝘱𝘳𝘰𝘷𝘪𝘥𝘦𝘥 𝘧𝘰𝘳 𝘦𝘥𝘶𝘤𝘢𝘵𝘪𝘰𝘯𝘢𝘭 𝘱𝘶𝘳𝘱𝘰𝘴𝘦𝘴 𝘰𝘯𝘭𝘺 𝘢𝘯𝘥 𝘪𝘴 𝘯𝘰𝘵 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘢𝘥𝘷𝘪𝘤𝘦 𝘰𝘳 𝘢𝘯 𝘰𝘧𝘧𝘦𝘳 𝘰𝘳 𝘴𝘢𝘭𝘦 𝘰𝘧 𝘢𝘯𝘺 𝘴𝘦𝘤𝘶𝘳𝘪𝘵𝘺 𝘰𝘳 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘱𝘳𝘰𝘥𝘶𝘤𝘵 𝘰𝘳 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘢𝘥𝘷𝘪𝘤𝘦. 𝘖𝘧𝘧𝘦𝘳𝘪𝘯𝘨𝘴 𝘢𝘳𝘦 𝘮𝘢𝘥𝘦 𝘰𝘯𝘭𝘺 𝘱𝘶𝘳𝘴𝘶𝘢𝘯𝘵 𝘵𝘰 𝘢 𝘱𝘳𝘪𝘷𝘢𝘵𝘦 𝘰𝘧𝘧𝘦𝘳𝘪𝘯𝘨 𝘮𝘦𝘮𝘰𝘳𝘢𝘯𝘥𝘶𝘮 𝘤𝘰𝘯𝘵𝘢𝘪𝘯𝘪𝘯𝘨 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘯𝘵 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯, 𝘸𝘩𝘪𝘤𝘩 𝘥𝘦𝘴𝘤𝘳𝘪𝘣𝘦𝘴 𝘳𝘪𝘴𝘬𝘴 𝘳𝘦𝘭𝘢𝘵𝘦𝘥 𝘵𝘰 𝘢𝘯 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘵𝘩𝘦𝘳𝘦𝘪𝘯 𝘢𝘯𝘥 𝘷𝘢𝘳𝘪𝘰𝘶𝘴 𝘰𝘵𝘩𝘦𝘳 𝘪𝘮𝘱𝘰𝘳𝘵𝘢𝘯𝘵 𝘮𝘢𝘵𝘵𝘦𝘳𝘴. 𝘐𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘤𝘰𝘯𝘵𝘢𝘪𝘯𝘦𝘥 𝘩𝘦𝘳𝘦𝘪𝘯 𝘪𝘴 𝘯𝘰𝘵 𝘪𝘯𝘵𝘦𝘯𝘥𝘦𝘥 𝘵𝘰 𝘣𝘦 𝘤𝘰𝘮𝘱𝘭𝘦𝘵𝘦 𝘰𝘳 𝘧𝘪𝘯𝘢𝘭 𝘢𝘯𝘥 𝘴𝘩𝘰𝘶𝘭𝘥 𝘯𝘰𝘵 𝘧𝘰𝘳𝘮 𝘵𝘩𝘦 𝘱𝘳𝘪𝘮𝘢𝘳𝘺 𝘣𝘢𝘴𝘪𝘴 𝘧𝘰𝘳 𝘢𝘯 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘥𝘦𝘤𝘪𝘴𝘪𝘰𝘯.
𝘛𝘩𝘦 𝘙𝘦𝘱𝘰𝘳𝘵 𝘪𝘴 𝘱𝘳𝘰𝘷𝘪𝘥𝘦𝘥 𝘧𝘰𝘳 𝘦𝘥𝘶𝘤𝘢𝘵𝘪𝘰𝘯𝘢𝘭 𝘱𝘶𝘳𝘱𝘰𝘴𝘦𝘴 𝘰𝘯𝘭𝘺 𝘢𝘯𝘥 𝘪𝘴 𝘴𝘰𝘭𝘦𝘭𝘺 𝘪𝘯𝘵𝘦𝘯𝘥𝘦𝘥 𝘵𝘰 𝘴𝘶𝘮𝘮𝘢𝘳𝘪𝘻𝘦 𝘓𝘦𝘷𝘦𝘭 𝘌𝘲𝘶𝘪𝘵𝘺’𝘴 𝘤𝘶𝘳𝘳𝘦𝘯𝘵 𝘰𝘣𝘴𝘦𝘳𝘷𝘢𝘵𝘪𝘰𝘯𝘴 𝘢𝘯𝘥 𝘷𝘪𝘦𝘸𝘴 𝘴𝘶𝘳𝘳𝘰𝘶𝘯𝘥𝘪𝘯𝘨 𝘵𝘳𝘦𝘯𝘥𝘴 𝘴𝘶𝘳𝘳𝘰𝘶𝘯𝘥𝘪𝘯𝘨 𝘴𝘰𝘧𝘵𝘸𝘢𝘳𝘦 𝘣𝘶𝘴𝘪𝘯𝘦𝘴𝘴𝘦𝘴. 𝘛𝘩𝘦 𝘙𝘦𝘱𝘰𝘳𝘵 𝘴𝘩𝘰𝘶𝘭𝘥 𝘯𝘰𝘵 𝘣𝘦 𝘳𝘦𝘭𝘪𝘦𝘥 𝘶𝘱𝘰𝘯 𝘧𝘰𝘳 𝘢𝘯𝘺 𝘰𝘵𝘩𝘦𝘳 𝘱𝘶𝘳𝘱𝘰𝘴𝘦. 𝘈𝘯𝘺 𝘷𝘪𝘦𝘸𝘴 𝘢𝘯𝘥 𝘰𝘱𝘪𝘯𝘪𝘰𝘯𝘴 𝘦𝘹𝘱𝘳𝘦𝘴𝘴𝘦𝘥 𝘪𝘯 𝘵𝘩𝘦 𝘙𝘦𝘱𝘰𝘳𝘵 𝘢𝘳𝘦 𝘵𝘩𝘰𝘴𝘦 𝘰𝘧 𝘓𝘦𝘷𝘦𝘭 𝘌𝘲𝘶𝘪𝘵𝘺 𝘢𝘯𝘥 𝘢𝘳𝘦 𝘣𝘢𝘴𝘦𝘥 𝘰𝘯 𝘢𝘷𝘢𝘪𝘭𝘢𝘣𝘭𝘦 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘢𝘯𝘥 𝘵𝘩𝘦𝘳𝘦 𝘪𝘴 𝘯𝘰 𝘪𝘮𝘱𝘭𝘪𝘤𝘢𝘵𝘪𝘰𝘯 𝘵𝘩𝘢𝘵 𝘵𝘩𝘦 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘤𝘰𝘯𝘵𝘢𝘪𝘯𝘦𝘥 𝘩𝘦𝘳𝘦𝘪𝘯 𝘪𝘴 𝘤𝘰𝘳𝘳𝘦𝘤𝘵 𝘢𝘴 𝘰𝘧 𝘢𝘯𝘺 𝘵𝘪𝘮𝘦 𝘴𝘶𝘣𝘴𝘦𝘲𝘶𝘦𝘯𝘵 𝘵𝘰 𝘴𝘶𝘤𝘩 𝘥𝘢𝘵𝘦.

Every boardroom has: Smart people. Solid data. Thoughtful preparation. Yet the direction diverges. Why?
Because board members are split into factions, each operating against a different threat. And until you name the risk, the debate goes in circles.

Let me explain:

THE FACTIONS IN THE BOARDROOM
The Sellers → "Winning fixes all problems." Push harder. 
The Savers → "Live to fight another day." Protect the runway. 
The Innovators → "Miss the platform shift and you're done." Move now on AI.

THE THREAT 
Over the years, the threat shifted:
In 2012, the dominant risk was missing growth. 
In 2022, it was insolvency. 
And, today, it is irrelevance.

Irrelevance does not show up in the pipeline until it's too late! It shows up in capital flows and customer expectations quietly reorganizing around AI-Natives. And at today's speed, by the time it shows in your numbers, the market has already moved.

THE QUESTION 
How do you govern the risk of irrelevance when the dashboard still says "stable"? The board's job is not to pick which faction wins. It is to decide which risks threaten the investment thesis — and act on it, deploying the company's resources.

David Spitz of BenchSights and I break down this boardroom collision in the attached article, as published in "Growth, Quarterly Insights for modern CEOs."

Action: Download the PDF, upload it to your LLM of choice, and prompt: 

"Read the attached article. Then ask me questions to identify which faction dominates our board. Then tell me which risk we are most likely ignoring — and how to make the case for addressing it."

#RevenueArchitecture

Founder, BenchSights | Former Software Investment Banker | Providing the premier software metrics benchmarking platform

BenchSights

How AI is impacting how the board operates

It was great to reconnect with Manny over a shared passion. The future of SaaS, in particular, as it relates to how it impacts growth.

Your SaaS company isn't losing to AI......

It's losing to your own users!

AI-native companies don't storm the front gate. They don't compete for logos. They walk in the side door, through individual users, and they win adoption one person at a time.

By the time you notice the logo at risk, the users are already gone.

Jacco van der Kooij calls it "user migration." The slow-motion disruption nobody sees coming.

The companies that survive this era aren't the ones with the best sales team. They're the ones who understand their dominant growth loop and build a system that compounds, without humans at the control stick.

If you're still celebrating seat counts, you're reading yesterday's scorecard.

New episode of Get Paid with Manny Medina with Manny Medina & Jacco is live. 👇

🎧 Apple: https://lnkd.in/eGCdZ5W2 
🎧 Spotify: https://lnkd.in/e-NC-EhP 
▶️ YouTube: https://lnkd.in/eDi6VpqN

#SaaSGrowth #AIStrategy #ProductLedGrowth #GetPaidPodcast #SaaSsales #GTM

What is the probability you’ll hit your 2026 growth target? 
Not the plan.
The probability.

Most executives don’t know.

With AI, you can now calculate it with precision, better yet, run a full simulation of your GTM system against your own data.

Soon, every board will ask for this.

On March 9–12 in San Francisco, I’m hosting a small, hands-on working session for executives who want to see/do it for themselves.

You bring your data.
Let's model your GTM system.
Let's run the simulation in your AI environment.

And we identify exactly which lever bends your curve toward the investor thesis:
• Is it Doing More
• Perhaps Doing Better
or
• Are you going all in on Growing Smarter

Not theory.
Your numbers
Your AI doing the math.

Seats are limited. Each participant gets desk space (2 per table) to work on their own computer and their own data.

If you want in and pressure-test your 2026 growth plan before your board does: DM Matt, Lauren, Shari or me for an invite.

taplio

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