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The future of AI-powered sales with Vercel COO, Jeanne DeWitt

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VideoLenny’s NewsletterDec 2, 2025
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Why GTM is becoming more strategically important in the AI era

  • Product differentiation is shrinking
    • There are often "10 players pursuing the same market opportunity."
    • Technical differentiation is only at the margins, so go-to-market becomes the strategic wedge.
  • The sales process is the product
    • Customers buy based on the experience of being sold to.
    • When tech is similar, a unique, human, and personalized buying journey becomes the deciding factor.
  • More consultative selling
    • Companies know they need AI but do not know exactly what to change.
    • GTM teams must act like consultants, not just order-takers.

  • The rise of the GTM Engineer

    The Go-to-Market Engineer (GTME) is a technical role that brings engineering and AI agents into the sales process.

  • The role
    • Breaks down GTM workflows and encodes them into AI agents.
    • Shadows high-performing humans (for example SDRs) to learn research and writing workflows, then builds agents to replicate that work.
  • Efficiency gains
    • Example: Vercel moved from 10 SDRs handling inbound leads to one human managing an AI agent, while maintaining similar conversion rates.
  • The profile
    • Often comes from sales engineering or technical backgrounds (for example front-end devs who moved into sales).
    • Understands both code and sales.

  • A primer on segmentation

  • Beyond small / medium / large
    • Size (SMB, mid-market, enterprise) is just the starting point.
  • Key attributes (the X and Y axes)
    • Growth potential
      • For consumption businesses (for example Stripe, Vercel), a small company growing 200% YoY can be more valuable than a large one growing 8%.
    • Business model
      • B2B vs B2C vs marketplace changes what products they need.
      • For example, a marketplace needs very different payments infra than a SaaS platform.
    • Technical signals
      • Vercel uses Crux scores (Google traffic data) and workload types (E‑commerce vs Crypto, etc.).
      • E‑commerce sites that rely on speed for revenue are a distinct segment from internal dashboards.
  • Implementation guidance
    • Start with about three attributes so the team can actually operationalize.
    • If you segment on too many dimensions, a small sales team cannot execute.

  • Building a sales org engineers and PMs respect

    Friction with engineering usually comes from sales lacking depth or making asks without product understanding.

  • The litmus test
    • “If I put you in front of 10 engineers, it should take them 10 minutes to figure out you are not a product manager.”
  • Sales as R&D
    • A world-class GTM org is an extension of R&D.
    • Sales talks to far more customers per week than PM or research, so they are a huge source of product insight.
  • Signal vs noise
    • To earn respect, sales must filter feedback well.
    • Distinguish between:
      • Objections that should be handled in the sales motion, vs.
      • Legitimate roadmap gaps.

  • The changing build vs buy calculus for GTM tools

    In the AI era, the bias is shifting toward building internal tools instead of buying SaaS for every micro-problem.

  • Low cost and high speed
    • Vercel built a lead-handling agent in six weeks with one engineer at ~30% allocation.
    • Running cost ≈ $1,000/year, versus > $1M/year in salary for the headcount it replaced.
  • Power of esoteric context
    • AI agents are best when they have access to your content, workflows, and data.
    • Off-the-shelf tools rarely embed this deep context.
  • Avoiding tool fatigue
    • Teams suffer from buying “20 different things” for narrow use cases.
    • CIOs and engineering leaders increasingly become builders of internal software, not just buyers.

  • Why most customers buy to avoid pain, not chase upside

  • The 80/20 rule
    • Roughly 80% of customers buy to avoid pain or reduce risk.
    • Only about 20% buy primarily to capture upside.
  • Career risk
    • Enterprise buyers treat software choices as career bets.
    • A failed deployment risks reputation and missed revenue targets.
    • The sale is often about de-risking the decision for them.
  • Messaging shift
    • Startups often over-index on visionary upside.
    • To sell into enterprise, highlight how you help them avoid falling behind, missing targets, or hurting their brand, as much as how you help them win.