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In this issue, we have:

  • RESEARCH: The evolution of GTM from 2021–2025, and what to expect in 2026
  • IN PRACTICE: Talking customer experience with Canva’s CCO
  • GROWTH INSTITUTE: The latest happenings – and some much-deserved recognition!
  • EVENTS: Secure your spot at Impact Summit 2026
  • IN CASE YOU MISSED IT: Pavilion partnership update
  • REVENUE ACADEMY COURSES: Enroll in upcoming courses across the Bowtie

RESEARCH: The Great GTM Reset — From SaaS to AI-Native

 

Between 2021 and 2025, the software world underwent its biggest shift since the rise of SaaS. Growth didn’t just slow—it broke.

 

Valuations crashed, playbooks failed, and what once powered hypergrowth suddenly couldn’t sustain it. But beneath the turbulence, something else was forming: a new architecture for growth.


The Rise of AI-Native GTM
Winning by Design’s latest Foundational Research Series traces this transformation across 50+ diagnostics and hundreds of companies. The findings are clear: the next generation of growth isn’t powered by people pushing harder—it’s powered by systems that learn faster.

The six-part chronicle from Jacco van der Kooij outlines the pattern:

  • The Collapse – SaaS growth stalls; the machine loses GTM fit.
  • The Reckoning – Efficiency replaces speed as the survival metric.
  • The Inflection – AI enters the workflow, first as assistant, then as operator.
  • The Rebuild – GTM architectures are re-engineered around data, loops, and automation.
  • The Resurgence – AI-Natives scale at 3–4x velocity, compounding through feedback loops.
  • The New Era – Growth now comes from system intelligence, not manual execution.

What’s emerging isn’t just a new set of tools—it’s a new operating model. In this model, AI doesn’t enhance the old GTM system; it replaces it.

Process First. AI Second.
One of the clearest takeaways from the research: before you scale AI, you must repair the system it will operate within.

Teams chasing “AI transformation” without process alignment are automating inefficiency. Those who standardize first—data, handoffs, and decision loops—unlock compounding growth once AI is layered in.

The New GTM Equation
AI-native growth follows a different math:

  • Human effort → System intelligence
  • Playbooks → Loops
  • Funnels → Feedback
  • Activity → Impact

The result? Faster cycles, lower cost of growth, and organizations that improve automatically as data compounds.

Why This Matters Now?
The companies that treat AI as an operating layer—not a project—are already pulling away. Their GTM teams don’t just execute faster; they learn faster. The difference is no longer technological—it’s architectural.

“Before companies can adopt AI at scale, they must repair the system it will operate within.” — Jacco van der Kooij


– Bottom Line –
The GTM revolution isn’t about new software—it’s about new structure. The winners of 2026 will be those who stop running harder and start designing smarter.

Explore the full Foundational Research Series to see how AI, data, and GTM systems are being re-architected for the decade ahead.

    A timeline chronicling the shifts redefining modern Go-to-Market strategy – from 2021 through 2025.

    Figure 1: A timeline chronicling the shifts redefining modern Go-to-Market strategy – from 2021 through 2025.

    IN PRACTICE: Designing Customer Experiences That Scale — Lessons from Canva’s CCO, Rob Giglio

    Most GTM leaders talk about being “customer-obsessed,” but few can operationalize it at enterprise scale. Rob Giglio, CCO of Canva—and former leader at Adobe, DocuSign, and HubSpot—has spent his career doing exactly that. His approach reveals a shift that mirrors a broader theme: durable growth comes from designing systems around the customer, not around the company.

    Build the System Around How Customers Think, Not How Teams Operate
    Giglio argues that most GTM motions break because they’re built from the inside out—organized around internal milestones rather than customer decision points. At Canva, he flips that paradigm.

    His team maps experiences using the customer’s language (“What problem are you trying to solve?”) rather than the company’s (“Which stage are you in?”). This creates alignment across marketing, sales, and success—and ultimately, smoother, more predictable revenue motion.


    The Power of a Single Shared Framework
    Throughout the interview, Giglio points to the same unlock: one shared process and one shared language.


    At Canva, that anchor is the SPICED framework.


    It prevents teams from reinventing the wheel, reduces friction between functions, and ensures every handoff is rooted in customer intent. Giglio emphasizes that this is what allows a company at Canva’s scale to maintain cohesion across hundreds of moments in the customer journey.


    Customer Signals > Internal Signals
    What sets Canva apart is how deeply it listens. Rather than overwhelming customers with choice or internal assumptions, Giglio’s teams rely on usage patterns, JTBD insights, and real customer signals to refine experiences.


    This is how Canva builds an onboarding motion that works across solopreneurs, global teams, and enterprise design departments—while maintaining simplicity for all.


    A Philosophy of “Substance Over Sizzle”
    Giglio’s mantra—substance over sizzle—runs counter to the conventional wisdom of hyper-polished GTM. His belief:


    When the product does the heavy lifting, growth teams can focus on clarity, not complexity.


    That philosophy shaped Adobe’s shift from packaged software to SaaS, DocuSign’s pandemic-era recovery, HubSpot’s inbound expansion—and now, Canva’s multi-segment PLG strategy.


    What’s most intriguing is how Giglio blends PLG, enterprise rigor, and AI-enabled automation into a unified operating system—a system that may foreshadow what the next generation of customer experience design will look like.


    – Bottom Line –
    Rob Giglio’s playbook shows that scalable growth isn’t about bigger teams or louder messaging—it’s about building a simple, shared system shaped entirely around the customer’s world, not your own.


    These insights are from a recent interview by Winning by Design CGO, Lauren Goldstein. The full interview can be found in our Growth Journal - subscribe here.

    Rob Giglio, CCO of Canva, participating in a panel discussion at a Canva event.

    Figure 2: Rob Giglio, CCO of Canva, participating in a panel discussion at a Canva event.

    GROWTH INSTITUTE: Key Conversations and Notable Accomplishments

    This week inside the Growth Institute, we ran our first live MBA-style case study—and it got spicy. Together, members stepped into the shoes of Dropbox’s strategic finance team circa 2016 and had to decide where to put the next $10M of growth investment:

    • Double down on inbound
    • Pour gas on outbound
    • Bet big on product-led growth from 500M free users.

    Over 60 minutes, the group:

    • Built real LTV/CAC models for inbound vs outbound and saw just how dramatically economics change at different ACVs and churn rates.
    • Applied the Bowtie and “do more / do better / grow smarter” factory models to pressure-test whether to hire more reps or instead improve conversion and routing.
    • Landed on a powerful insight: the biggest upside often isn’t “more leads” or “more headcount,” but focusing reps on the crème de la crème PQLs—high-usage accounts that are a perfect ICP fit.

    If you weren’t in the (virtual) room, you missed the debate, the live math, and the “aha” moments as the optimal strategy emerged.

    Don’t miss the next one. Join the Growth Institute and be in the room for our next live case study session.

    Congratulations are in Order!
    We want to give a special shoutout to three Growth Institute Members that have seized the benefits of their membership, enrolling in – and earning certification in – our new Growth Architecture course!

    • Amit Soni
    • Tim Busschops
    • Alessandro Bodo
    • Pedro Miquelasso

    Here's what the learners had to say:

    "Jacco’s Growth Architecture course masterfully proves that growth is a science, showing how to move beyond rear-view metrics to predict the future using AI-fueled growth loops. Winning by Design transforms growth from a guessing game into a predictable science where AI-powered loops, not past performance, become the accelerator for future revenue. This course is essential for leaders ready to stop managing by analogy and start engineering the future through first principle thinking and science-backed, AI-fueled growth loops."

    
    
    “Jacco is the best. Truly inspiring and it was an honor to be in this first class. It was intense but really insightful.”

    This is not an easy curriculum to master, but you have put in the work and will reap the benefits. Round of applause to you all!

    EVENTS: Excited for You to Join Us in the Coming Months!

    ⭐ IMPACT SUMMIT 2026 IS 5 MONTHS AWAY! | SAN FRANCISCO | MAY 12, 2026 / Get ready! The second annual Impact Summit is coming on May 12, 2026, live from San Francisco. From a high-impact keynote by Jacco van der Kooij to expert roundtables and eight cutting-edge research guides, this year's Summit will deliver the most practical, future-ready GTM intelligence of the year. Request an invite.

    jacco presenting at Impact Summit
    Impact Summit networking

    Want to get in front of GTM Executives of industry-defining companies? Sponsorship slots are still open!

    Sponsorship Packages

    - OPEN WORKSHOP: GROWTH ARCHITECTURE PRIMER | WATCH THE RECORDING / On November 19th, Jacco held our (highest attended!) workshop, where he walked through how leading “AI-Native” companies achieve breakout velocity without proportional headcount growth and how to apply those lessons to your own revenue architecture—creating systems that compound, rather than decay. Watch the recording.

    ICYMI: Pavilion Partnership Update

    Over the past year, we’ve been working on a bold next step for Winning by Design — the launch of the Growth Institute. This new community brings together our courses, our research, and a global network of GTM leaders under one shared mission: to build a universal, science-based language of growth.

    The Growth Institute creates one connected home for all of our growth courses and community at the forefront of everything we’re building next. It’s a place where leaders can deepen their expertise, stay on the cutting edge of GTM innovation, and grow alongside peers who are committed to operating with rigor, clarity, and impact.

    As we align our programs inside this new vision, transitions are a natural part of the journey. Our goal is to provide an even more cohesive and transformative learning experience for every GTM operator who chooses to grow with us.


    Effective November 21st, Pavilion members will no longer be able to register for Revenue Architecture and Essentials in Revenue Architecture courses through their Pavilion membership. However, they can sign up through Winning by Design’s Revenue Academy or receive access via Growth Institute Membership.

    While this is a change, it’s also the start of something bigger. We hope to have you join us on the journey.

    REVENUE ACADEMY COURSES: Uplevel your skills across the GTM

    Sign up for Revenue Academy Open Courses —next cohorts are kicking off on January 6th.

    • Selling for Impact (US) (EMEA)
    • Selling into Enterprise Accounts (US) (available only once per quarter)
    • Prospecting for Impact (US) (EMEA)
    • Prospecting into Enterprise Accounts (US) (available only once per quarter)
    • Customer Success for Impact (US) (EMEA)
    • Account Management for Growth (US) (available only once per quarter)
    • Managing for Impact (US) (EMEA)
    • Managing for Leadership (US) (available only once per quarter)
    • Revenue Architecture (US) (EMEA)
      • Essentials in Revenue Architecture (Single-Session) (US) (available only once per quarter)
      • Essentials in Revenue Architecture (Self-Paced) (US)
    • NEW! Growth Architecture (available only once per quarter)
    • Bowtie Analytics (US) (available only once per quarter)
    • Insight Engineering (US) (available only once per quarter)
    • Skills Course: Discovery Using SPICED (US) (available only once per quarter)
    • Skills Course: Storytelling (US) (available only once per quarter)
    • Facilitator Certification (US) (available only once per quarter)
    • Complimentary SPICED Micro-Course (Self-Paced)

    Cheers to a great month ahead and a strong finish to 2025.

     

    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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