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Hello Friend,

In this issue, we have:

  • RESEARCH:  Why AI is delivering in product but not yet in revenue

  • IN PRACTICE:  Why AI is filling the funnel but not closing it, and what the teams pulling ahead built first
  • EVENTS: A live webinar, a live Impact session in SF, and a 4-city European Roadshow
  • KICKOFF SEASON: Announcing the 2027 kickoff season lineup
  • GROWTH INSIGHTS QUESTION OF THE MONTH: What's the biggest driver of rising the GTM Spend Ratio in SaaS right now?
  • REVENUE ACADEMY COURSES: Enroll in upcoming courses across the Bowtie

RESEARCH: Why AI Is Working in Product and Not Yet in Revenue

 

Your board has a new question this year. Engineering is shipping AI-driven gains. Revenue is not. Why?

The honest answer is not the one most teams fear. It is not your people. GTM entered the AI game later, and it entered a harder game.

Product runs on code. Code is centralized, controlled, and observable. Tests, logs, and diffs show exactly what happened and whether it worked. That is a native feedback loop, and AI improves fastest where feedback loops already exist.

GTM runs on people. People are spread across reps, channels, calls, and inboxes. No two deals are the same. Most of what decides a deal happens off-system, in a room you were not in. GTM behavior is not observable by default, so the feedback loop has to be built before AI can compound.

Product behavior is visible by default. GTM behavior is not. That one difference is worth about a two-year head start.

This is why most AI spend in revenue has not produced growth. Teams funded the move from Literacy to Fluency. A budget line, fifty dollars a month per person, go use it. People got faster at drafting, summarizing, and researching. Real gains. But Fluency was never the goal. Productivity is.

A seller who writes emails three times faster in a market where email no longer converts has not created growth.

Here is the part worth sitting with. Almost no one outside Silicon Valley has deployed AI into anything that touches revenue yet. And no one anywhere, including in the Valley, has finished the move to Productivity. Being eighteen months behind is not the disadvantage it gets sold as. It is eighteen months of watching other people pay for the lessons.

– Bottom Line –
Engineering is not smarter than your revenue team. It started earlier, in an environment where AI could learn faster. The edge now goes to leaders who build the feedback loop GTM never had, and who fund Productivity instead of mistaking Fluency for it.


These insights are adapted from an Executive Brief authored by Jacco van der Kooij, Founder & CEO of Winning by Design. The full piece can be found on Linkedin - read here.

    Figure 1: AI adoption moves through three stages, from understanding the tools to using them to create growth. Most GTM organizations fund and celebrate the jump to Fluency, but the dashed line marks the step that actually produces revenue, and it is the one most teams have not yet crossed. 

    IN PRACTICE: AI Is Not the Advantage. The System Around It Is.

    Nearly every B2B company is now using AI in its go-to-market motion. Ask a revenue leader what it is doing and you will hear about tools, workflows, and hours saved. Ask the board what it is doing for growth and the room goes quiet.

    That gap is the story of AI in GTM right now, and it is the one Dan Kimball takes apart in the latest Growth Journal. A GTM operating partner and former CMO, Kimball has spent the past few years advising companies on AI-enabled go-to-market. His read is direct. Adoption is everywhere. Impact is uneven. Some companies are working harder just to hold the growth rate they already had, while absorbing the new cost of the tools.

    The gap is not a tools problem. It is a systems problem.

    The companies turning AI into real growth share a pattern. One shared definition of the ideal customer. Connected data. Joint accountability across functions. Clear rules for where AI investment goes.

    AI is already moving the top of the funnel. Companies with AI embedded across GTM convert 11 points more raw leads into qualified pipeline and 8 points more into sales-ready opportunities. Then the gain nearly vanishes at close, where the lift is a single point. AI is filling the funnel. Converting it is still a human system, and in most companies that system has not been redesigned.

    The gains leak at the seams. Data that AI amplifies before it is clean. An ICP that has not been revalidated in eighteen months. Marketing running AI while sales still runs manual, so lead quality improves and then the lead sits in a queue for three days. A leadership team that reviews pipeline and revenue, but never reviews how the AI-driven system is performing as one thing.

    Close those seams and the numbers move. Kimball points to companies with AI fully embedded across GTM hitting 67% quota attainment against 59% for their peers. Among strategic sellers the gap is wider, 109% of quota against 88%. They also run leaner. Faster growth, fewer people.

    The move that separates them is not a bigger AI budget. It is sequence. Diagnose where the system is leaking revenue first. Then point AI at the leak. Not the other way around.

    – Bottom Line –
    AI does not fix a blurry ICP or a broken handoff. It amplifies whatever you feed it. The teams pulling ahead did not adopt AI the fastest. They built the system that made it compound.

    These insights are adapted from an article authored by Dan Kimball, a GTM operating Partner and former CMO. The full piece can be found in the latest edition of our Growth Journal - subscribe here (or read here if already subscribed).

    Figure 2: A full-cycle view of AI in go-to-market, from signal capture to loop closure and back. The value does not leak inside the stages. It leaks at the seams between them, which is where the checkpoints sit.

    EVENTS: Where the AI-and-GTM Conversation Is Happening This Fall

    >> LIVE WEBINAR: SECRETS FROM THE STAGE: 350 KICKOFFS IN, HERE'S WHAT ACTUALLY WORKS | SEPTEMBER 29, 2026 | VIA ZOOM / If a 2027 kickoff is on your calendar, spend 45 minutes with three WbD kickoff experts on what separates the ones people just remember from the ones that move revenue. Melissa Huggett on building content your team actually cares about. Antoine Mandy on making it stick in the room. Patrick McGrann on the 90 days after, where adoption is won or lost. Stories from what has worked and what has failed across 350-plus sessions, plus live Q&A.


    Register here.

    >> IMPACT SUMMER SERIES | Q3 2026 | BAY AREA / Every GTM leader is asking the same question. How do you get real value from AI without losing what makes your reps good at their jobs? This is a working session for a hand-picked group of Bay Area revenue leaders. AI amplifies good selling. It does not replace it. We will focus on where AI moves the needle and where your team still does the work.

    September 17 San Francisco > Reserve your spot 

    >> IMPACT ROADSHOW EUROPE | OCTOBER, 2026 / Our four-city European roadshow lands in October. Half-day sessions. Rooms built for the market they are in. Real discussion, not keynote-and-out. Every location still has room. 

     

    October 5 in Amsterdam > Reserve your spot
    October 6 in Ghent > Reserve your spot
    October 7 in London > Reserve your spot
    October 12 in Stockholm > Reserve your spot

    >> PRIOR WEBINAR: BACK TO GROWTH — ENGINEERING AI INTO YOUR GTM PERFORMANCE | WATCH THE RECORDING ON-DEMAND / Your board wants to know what AI is doing to your growth engine. Most CROs still cannot give a straight answer. In this session from last month, Jacco van der Kooij returns to the fundamentals of performance management and lays out a working model for where AI belongs in your growth engine, built with the same science and method WbD applies to any revenue system. 


    Watch the recording here.

    KICKOFF SEASON: Make Your 2027 Kickoff the One That Moves the Number

    Most sessions create energy. Few create change. A Winning by Design kickoff installs one shared method your team runs the Monday after, reinforces it with manager coaching, and measures what actually moved 90 days later. If the indicators have not moved, we keep coaching until they do.

    Our 2027 workshop topics are shaped by feedback from over 700 participants from 2026 and over 50 prior kickoffs. These are the sessions that consistently move the number. Every one can be tailored to your team, your deals, and your motion:

    • Full SPICED
    • Discovery Using SPICED
    • Impact: Rational and Emotional
    • Closing: Critical Event and Decision Process
    • Provocative Selling
    • SPICED and Storytelling
    • Executive Storytelling and Influence
    • Coaching for Managers
    • Prospecting
    • AI for GTM

    Pick one as an anchor or stack several across a full agenda. Custom topics are available on request.

    Elevate Your RKO Impact with Winning by Design (2026-27)

    >> Start planning your kickoff with WbD!

    GROWTH INSIGHTS QUESTION OF THE MONTH

    GTM Spend Ratio (S&M spend divided by Net New ARR) has climbed sharply, moving from roughly 150% a few years ago to around 250-264% now. (Source: Benchsights data from David Spitz)

    In your opinion, what's the biggest driver of the rising ratio right now?

    Buying committees

    Buying committees have gotten bigger and slower, deals just take longer to close

    Churn & Contraction

    Churn and contraction are quietly eating net new ARR, inflating the ratio

    Overspending

    Companies kept spending on S&M without adjusting to slower growth

    Inefficient Tactics

    Too many overlapping channels/tools, nobody's consolidated the stack


    RESULTS FROM LAST MONTH'S QUESTION

     What would help your team close more deals this quarter? 

    1. Multi-threading: getting the right stakeholders into the deal, not just your champion - 27%
    2. Storytelling: building trust and making your value memorable - 27%
    3. Finding the critical event: the moment that turns urgency into a real deadline - 21%
    4. Using AI to surface the selling insights hiding in your calls - 25%

    REVENUE ACADEMY COURSES: Uplevel Your Skills Across the GTM

    Sign up for Revenue Academy Open Courses —  the next cohort kicks off on September 15th (with cohorts scheduled throughout Q3 and Q4).

    See All Upcoming Courses
    View 2026 Course Catalog

    Here's to a great month ahead. Remember, AI will not hand anyone growth. The system you build around it will.



    To impact!

    The crew @ Winning by Design

    Winning by Design, 650 Castro Street, Suite 120-252, Mountain View,California,94041,US,415-484-8992


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