Lessons from Jacco van der Kooij, founder of Winning by Design

Jacco van der Kooij is the founder of Winning by Design, a global growth advisory firm that helps B2B recurring revenue companies build scalable go-to-market strategies. He is the creator of several foundational sales frameworks, including the Bowtie Model and SPICED qualification, and the author of Revenue Architecture. A prominent thought leader in B2B SaaS, Jacco advocates for a scientific, systems-based approach to revenue generation, emphasizing that sustainable growth beyond the initial stages relies heavily on customer retention and recurring impact rather than acquisition alone.

On the Philosophy of Sales

On buyers who hate being pitched: In his 2024 write-up Jacco lists the principle "Buyers Hate Being Pitched, They Love Buying: Stop the hard sell and focus on empowering their buying journey." — Winning by Design: Back to the Future, process first, AI second (June 2024).
"I think we should help our customers solve their problems." [2]
On buyers calling the shots: Jacco writes "Buyers Call the Shots: Adapt the sales approach to cater to real-time interactions." — Winning by Design: Back to the Future, process first, AI second (June 2024).
On how you sell and what you sell: Revenue.io's summary of the episode says "When organizations treat how they sell, as important as what they sell, then sales will work." — Revenue.io podcast, episode 528: How to Fix the Failing Sales Model, with Jacco van der Kooij (archived February 2025).
On sales as a science: The CRO Club quotes The SaaS Sales Method: "In SaaS, sales isn't just an art—a science. And like any science, it demands precision, understanding, and a method." — The CRO Club: The Top 17 SaaS Books to Read in 2025.
"We're not the first to say “prescription without diagnosis is malpractice,” but it is still very true." [5]
" The number one factor that makes a great sales experience is when the salesperson makes you feel that their recommendations are in your best interest, not theirs.” InAccord 10-10 GTM: Growth, Discipline and Effective GTM with Jacco van der Kooij
On sales as service: Revenue.io's summary says "Sales is service," and quotes Jeff Bezos: "We don’t make money when we sell things. We make money when we help customers make purchase decisions." — Revenue.io podcast, episode 528: How to Fix the Failing Sales Model, with Jacco van der Kooij (archived February 2025).
On joy over performance: Selling Power reports that Jacco "believes that joy should always be prioritized over performance." — Selling Power: The Power of Design Thinking with Winning by Design.
On money coming second: Jacco said of why he started Winning by Design "The money is secondary. It’s important as anything, but it is not the lead." — GTMnow podcast 145: Lessons Learned From Winning by Design with Jacco van der Kooij (January 2021)
On helping the winners win: Jacco said sales teams should "help the winners win," because those winners, "when they’re going fast, they’re going way, way faster." — GTMnow podcast 145: Lessons Learned From Winning by Design with Jacco van der Kooij (January 2021)
On recurring impact: Jacco said "in order to achieve recurring revenue, you have to deliver recurring impact. No recurring impact, no recurring revenue." — GTMnow podcast 145: Lessons Learned From Winning by Design with Jacco van der Kooij (January 2021)
On sales as first responders: Jacco urged sales professionals "to consider ourselves the first responders of the economy" and to help put people back to work. — GTMnow podcast 145: Lessons Learned From Winning by Design with Jacco van der Kooij (January 2021)
On talking to customers directly: Jacco said "I talk to customers almost every day. Why do I need to listen to somebody else’s interpretation that I don’t know which customers they talk about?" — GTMnow podcast 145: Lessons Learned From Winning by Design with Jacco van der Kooij (January 2021)

On Sales Process and Methodology

On what a process is: Revenue.io's summary says "A process is doing something that is proven to work, and doing more of it, while stopping what doesn't work." — Revenue.io podcast, episode 528: How to Fix the Failing Sales Model, with Jacco van der Kooij (archived February 2025).
On executing a process consistently: Revenue.io's takeaways say Jacco states "the single biggest challenge facing sales professionals is that they are unable to execute a proper sales process consistently." — Revenue.io podcast, episode 528: How to Fix the Failing Sales Model, with Jacco van der Kooij (archived February 2025).
On land and expand: Winning by Design's blueprint calls "Land and expand" "a buzzword" and "a metaphor rooted in conflict," and recommends that expansion teams think about growing the customer relationship instead. — Winning by Design: Blueprint, The SaaS Sales Method.
On committing and trading: Revenue.io's summary says "Think Committing, not closing; Trading, not negotiating." — Revenue.io podcast, episode 528: How to Fix the Failing Sales Model, with Jacco van der Kooij (archived February 2025).
"We recommend that salespeople think of negotiation as “trading.” With trading, both parties give up something of value in order to benefit." [5]
On the trade at the heart of sales: Revenue.io's summary says "The trade in the heart of sales is the customer's time for the salesperson's value." — Revenue.io podcast, episode 528: How to Fix the Failing Sales Model, with Jacco van der Kooij (archived February 2025).
On experiences, not stages: Revenue.io's summary says "The methodology must become customer-centric: experiences, not stages. The experiences are emotional steps." — Revenue.io podcast, episode 528: How to Fix the Failing Sales Model, with Jacco van der Kooij (archived February 2025).
"Come up with a plan for how your teams can improve each of these conversion rates with a few basic actions." [5]
On repeatable action: Explaining why he gravitated to process-driven sales from his engineering background, Jacco said "Perform the same action, get the same result." — GTMnow podcast 145: Lessons Learned From Winning by Design with Jacco van der Kooij (January 2021)
On conversation, not qualification: The blueprint says "Conversation is a more natural, more human activity," and that it helps you "connect with the prospect on an emotional level." — Winning by Design: Blueprint, The SaaS Sales Method
On impact reframing fit: The blueprint says "In the SaaS Sales Method, the concept of “fit” is reframed by impact." — Winning by Design: Blueprint, The SaaS Sales Method
On orchestrating, not onboarding: The blueprint says to treat the first engagement after commitment as "an opportunity to orchestrate the entire business relationship going forward." — Winning by Design: Blueprint, The SaaS Sales Method
On results, not usage: The blueprint notes that product usage "is often a proxy for success," but "the software doesn’t measure the success of the customer, but rather the success of the product itself." — Winning by Design: Blueprint, The SaaS Sales Method
On discounts and trading: The blueprint says "most deals that reach the negotiation stage seldom turn on price," and that trading can cause the average discount to drop "say, from 20% to 10%." — Winning by Design: Blueprint, The SaaS Sales Method
On three process mistakes: InAccord's write-up lists three common go-to-market mistakes: "Wrong process, well executed," "Right process, poor execution," and "No process in place." — InAccord 10-10 GTM: Growth, Discipline and Effective GTM with Jacco van der Kooij

On Growth and Retention

"Up to $10M, growth primarily comes from acquiring new customers. Beyond this, growth comes mostly from retention." InAccord 10-10 GTM: Growth, Discipline and Effective GTM with Jacco van der Kooij
"Retention needs to be seen as the same as acquisition. It's an element of growth.” InAccord 10-10 GTM: Growth, Discipline and Effective GTM with Jacco van der Kooij
"Retention behaves the same way as acquisition. The customer needs to be convinced that the impact is still there, and if you don't do that, they won't renew.” InAccord 10-10 GTM: Growth, Discipline and Effective GTM with Jacco van der Kooij
On the end of growth at all costs: RevCity's write-up of his keynote says historically growth was driven by a "growth at all costs" approach, but "this is no longer feasible." — RevCity by 6sense: Building a Revenue Factory, Jacco van der Kooij.
On recurring impact: RevCity's write-up of his keynote says "Recurring impact leads to recurring revenue." — RevCity by 6sense: Building a Revenue Factory, Jacco van der Kooij.
On expansion as its own function: Jacco writes "success in Phase III depends on the organization treating Expansion as its own function, not as an afterthought of Acquisition." — Winning by Design: Back to the Future, process first, AI second (June 2024)
On not shifting sales to upselling in a downturn: Jacco said "you cannot shift during this moment of downturn your sales resources to start upselling and cross selling customers because the cost of that is way way way too high." — Video: The SaaS Reset and what's next, with Jacco van der Kooij
On the bowtie: RevCity's write-up says recurring revenue "requires extending the funnel into a bowtie model, emphasising onboarding, retention, and expansion." — RevCity by 6sense: Building a Revenue Factory, Jacco van der Kooij

On the Role of AI and Technology

On AI and a flawed design: Jacco writes "AI is like a souped-up rocket engine, which can propel us to new heights, but any flaws in its design will cause it to crash faster." — Winning by Design: Back to the Future, process first, AI second (June 2024).
On AI and GTM processes: Jacco writes "Just like automation relies on well-oiled factory processes, AI thrives on robust GTM processes." — Winning by Design: Back to the Future, process first, AI second (June 2024).
On drilling into rotten floorboards: Jacco writes "if we're drilling into rotten floorboards, we're just going to make bigger holes. AI can't fix underlying issues in the GTM processes. In fact, it might even amplify them." — Winning by Design: Back to the Future, process first, AI second (June 2024)
On AI flipping the symmetry of SaaS: Jacco is quoted saying "AI is flipping the symmetry of SaaS. The buyer has the earlier advantage and is already using AI systems to write proof of concepts, while the seller is trying to figure out how to use AI to proofread emails to the customer." — InAccord 10-10 GTM: Growth, Discipline and Effective GTM with Jacco van der Kooij
"AI is the strongest where we close loops where we bring lots of data together we draw insights from that." [13]
"AI is consumer grade not enterprise grade... I cannot trust it in the enterprise." [14]
On AI and the buyer experience: Jacco writes "Leverage AI to elevate the buyer experience. It's not about giving sellers an unfair advantage–it's about using AI to make things easier for buyers." — Winning by Design: Back to the Future, process first, AI second (June 2024).
On activity and productivity: Selling Power reports that Jacco believes the shift from activity to productivity is "the major shift that needs to be addressed," and that turning activity into productivity takes "knowledge and skill." — Selling Power: The Power of Design Thinking with Winning by Design.
On activities versus jobs: The Revenue Formula's notes say "It’s not necessarily that 70% of jobs get replaced, but 70% of activities most likely will." — The Revenue Formula: Why 70% of Sales Jobs Might Disappear (with Jacco van der Kooij).
On agents and knowledge: The Revenue Formula's notes say agents "are constantly iterating and improving - and they will never walk out of the door with their knowledge." — The Revenue Formula: Why 70% of Sales Jobs Might Disappear (with Jacco van der Kooij).
On moving past pain: The Revenue Formula's notes say "70% of sellers start pitching after they learn the pain. AI is advancing the conversation much further before pitching." — The Revenue Formula: Why 70% of Sales Jobs Might Disappear (with Jacco van der Kooij).
On a first-mover opportunity: The Revenue Formula's notes say companies "are presented with an opportunity: zero day exploit," like Amazon when Google Ads launched, which "gave them an unfair advantage." — The Revenue Formula: Why 70% of Sales Jobs Might Disappear (with Jacco van der Kooij).

On Team Building, Learning, and Culture

"I don't hire sales people... early on what you'll do as a as a founder CEO... they understand the problem really well... what I generally recommend is that you hire people who are passionate about solving the same problem or passionate about having the same solution." [15]
"The true expertise of selling at every GTM motion, from PLG to deep enterprise, needs to be properly taught and educated." InAccord 10-10 GTM: Growth, Discipline and Effective GTM with Jacco van der Kooij
"I like a person that fails in front of me. I like a person that has things that I see that they're failing. And I like to see how they deal with that failure. I don't like people who are perfect." [2]
On measuring productivity: Jacco said "Today in the remote world, we need to look at people, at the productivity that they’re generating, not just their activity or their presence." — GTMnow podcast 145: Lessons Learned From Winning by Design with Jacco van der Kooij (January 2021)
On knowing when to quit: Jacco said "knowing when to quit is the real key skill." — GTMnow podcast 145: Lessons Learned From Winning by Design with Jacco van der Kooij (January 2021)

On Communication and Customer Conversations

On customer conversations: The CRO Club quotes the book: "Customer conversations are more than transactions; they are the bridges that connect a product's potential to a client's need." — The CRO Club: The Top 17 SaaS Books to Read in 2025.
On asynchronous video follow-ups: Jacco described asynchronous selling as "an interaction in which I can record it at the time and place I want it, send it over to you, and you can watch it at the time and place you want it." — GTMnow podcast 145: Lessons Learned From Winning by Design with Jacco van der Kooij (January 2021)
On customer-centric engagement: SoBrief's summary of the book says "Effective customer engagement starts with a customer-centric methodology." — SoBrief: The SaaS Sales Method, summary.
On active listening: SoBrief's summary of the book defines active listening as "mindfully listening to your customers, building on the response they are giving, and providing cues that show them that you're actually comprehending what they are saying." — SoBrief: The SaaS Sales Method, summary.
On avoiding interrogation: SoBrief's summary of the book advises "Avoid making it feel like an interrogation. Identify pain and impact." — SoBrief: The SaaS Sales Method, summary.
On the TALKER acronym: Revenue.io's summary says Jacco "uses TALKER as an acronym for Tone, Ask questions, Listen actively, Keeping notes, Elaborate on the conversation, Repeat what you’ve heard." — Revenue.io podcast, episode 528: How to Fix the Failing Sales Model, with Jacco van der Kooij (archived February 2025).
On making it about the customer: SoBrief's summary of the book advises "Avoid starting with 'I' statements; make it about the customer ('You')." — SoBrief: The SaaS Sales Method, summary.
On the knowledge reversal: Jacco's 2024 write-up has a section headed "AI is causing buyers to have more knowledge than sellers," and says that today "buyers are the ones with all the knowledge." — Winning by Design: Back to the Future, process first, AI second (June 2024).

On Mindset and the Future

"By the time you get to this particular point you're stubborn... it's the only way how you get here right if you haven't listened to all the naysayers you would have never gotten here." [15]
On the Revenue Factory era: RevCity's write-up of his 2024 keynote says "the era of the Revenue Factory" followed the end of "growth at all costs" in 2022. — RevCity by 6sense: Building a Revenue Factory, Jacco van der Kooij.

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