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"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel

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Video•Lenny’s Newsletter•Nov 9, 2025
PricingGTMSales

Why the “mid-market” doesn’t exist

There is no real "hybrid" sales approach for the middle.

  • You are either playing a small business game (marketing-led) or an enterprise game (sales-led).
  • Blending the two usually fails because selling to a 100-person org is radically different from selling to a 1,000-person org.
  • You need to choose:
    • Upper end of small business, or
    • Lower end of enterprise.
  • That choice drives who you hire and what ACV you target.

    • Why tier-one logos make the best early customers

    Tier-one logos like Stripe, Tesla, Walmart, NVIDIA are often the true early adopters.

  • They must constantly innovate to stay number one.
  • Lower-tier companies often just want to copy leaders later.
  • Winning a tier-one logo:
    • Validates your product to the rest of the market.
    • Attracts talent.
    • Excites investors.
  • Smaller logos rarely create the same pull.

    • The danger of pricing at $10K–$20K

    Anchoring your price too low creates serious downstream issues:

  • False signals
    • If a large company is nickel-and-diming you, they are not truly bought in.
    • Low prices can give a false sense of PMF with customers who will not do the hard work to implement.
  • Anchoring
    • A client closed at $10K is very hard to move to $100K later.
    • You cannot easily prove a 10x jump in value.
  • Lack of seriousness
    • Enterprise buyers do not treat $10K deals as strategic.
    • A $100K deal forces executive sign-off and real internal commitment.
    • That “skin in the game” is what makes implementations succeed.

    • Vision-cast vs. problem-solve

    To win enterprise deals, you need to vision-cast, not just fix a tactical problem.

  • Pure problem-solving feels technical, tactical, and scripted.
  • It can kill the emotional momentum of a deal.
  • Executives buy when you sell the opportunity (the gap):
    • Show how they gain a speed advantage, an information advantage, or a strategic edge.
  • This is “selling the alpha,” not just the feature list.

    • Why services are often the fastest enterprise wedge

    Services are often the quickest way to get in the door.

  • Enterprises are used to buying services. It is often their largest, most flexible budget line.
  • Selling a service lets you:
    • Solve the problem for them right away.
    • Use your software behind the scenes, without heavy upfront integration.
    • Avoid early procurement and security blockers.
  • You can often charge $75K–$150K for services from day one.
  • Over time, you transition them from services into the product as trust builds.

    • When to hire your first salesperson (and who)

  • When to hire
    • Around $1M ARR, after the founder has closed 7–10 customers and built pattern recognition.
    • Founder must own the 0 → 1 sales motion first.
  • What profile to hire
    • Do not hire a big-company VP of Sales used to selling with a famous brand.
    • Look for someone who can “cosplay a founder”:
      • Vision-cast.
      • Craft creative deals.
      • Build trust without a playbook.
    • This may be a former founder or someone with deep product expertise, even without classic sales titles.
  • Structure the team and comp
    • Ideally hire two sellers at once, since the failure rate is ~50%.
    • Compensation roughly 50% base / 50% commission to align incentives.