Jen Abel: The Mid-Market Trap in Enterprise Sales

Why the Mid-Market Is a Trap for B2B Founders

This is Jen Abel - co-founder of Jellyfish, now GMF Enterprise at State Affairs - with part two of her enterprise sales masterclass. This one covers $1M to $10M ARR, and her advice is consistently counterintuitive.

"The mid-market doesn't exist." Ask people to define it and everyone has different answers. Really, you're either playing upper-end small business (marketing-led, self-serve) or lower-end enterprise (sales-led, relationship-driven). If you bleed these two games, you lose. Know which game you're playing.

"Go after tier-one logos first." Walmart, Nvidia, McDonald's. This is the opposite of conventional VC advice. The logic: tier-ones have to stay #1, so they'll take swings on anything that gives them alpha. They also want to influence your roadmap. A YC company launching next week can land a Fortune 10 if they vision-cast correctly.

Vision-casting versus problem-selling. Problem-selling is finding a specific pain point and anchoring to it. That's what every trained salesperson does. Vision-casting is selling the gap between where they are and where they could be. Don't sell the mushroom - sell Mario on Blast. "Here's how you become a superhero because of what we built."

Your initial price anchors everything. If you land at $10K with Walmart, then try to expand to $100K, procurement will ask "What's the 10x value difference?" That's impossible to defend. Start at $75K-$150K - enterprises are used to that range. Leave room to expand, but don't sell the farm.

Design partners rarely convert. They're the hardest logos to upsell because they've seen you when you were messy and got a low price. Expect them to guide your roadmap, not become your $1M pipeline. If you do convert one, it's a huge market signal.

10 Insights From Jen Abel on Scaling to $10M ARR

• Mid-market doesn't exist - Upper-end SMB or lower-end enterprise; don't bleed games
• Tier-ones are early adopters - They need alpha to stay #1; will take swings
• Vision-cast, don't problem-sell - Sell the gap, not the pain; sell the superhero
• $75K-$150K starting ACV - Enterprises expect this; leaves room for expansion
• $10K deals break math - Can't defend 10x expansion; commission too low for good salespeople
• Design partners rarely convert - Hardest upsell; use them for roadmap guidance
• AI tools pull from same databases - Jen doesn't use them; prefers back doors over front doors
• Get founder involved - Everyone loves talking to founders; brings the vision
• Defendable pricing - All expansion needs to be explainable to procurement AI
• Differentiation > comparison - Once you're "one of three being tested," you've lost

What This Means for Early-Stage Enterprise Startups

The mid-market is a trap - you're either playing upper-end small business (marketing-led) or lower-end enterprise (sales-led). Most counterintuitively: tier-one logos are early adopters because they need alpha to stay #1. A YC company launching next week can land a Fortune 10.