Enterprise win rates above 35% mean you're priced too low
A healthy enterprise win rate is 25% to 35%. Above that range isn't strong selling, it's underpricing — the market talks to itself, and the worst case is quoting 50 to one person's friend and 500K to another.
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The argument · tap a timestamp to hear it
Only work two levels, never go lower
Jen compresses the entry point of enterprise sales into two: the decision maker themselves (a chief legal officer, a general counsel) or N minus one. Go lower and what you hear is user value, not executive value — and the middle becomes a game of telephone, because that person sits too far from the budget and the decision discussion. A $100K deal needs an executive sponsor to sign off on budget. Her approach is the pincer model: the founder works from the very top, the AE works from N minus one, both push at the same time, and eventually you get everyone in the same room.
— Jen AbelThose two sentences have to carry alpha, not AI
Every company has an AI mandate today, so saying you're an AI tool is not a reason. Jen wants two to three sentences that make clear what this executive unlocks, what they get, by bringing in a brand-new tool. Because bringing in a new tool is itself a risk, and nobody wants that. Her test: if this pitch landed in a board meeting, what would he say? "This product lets me do what" is the litmus test. C-level people basically don't read marketing campaigns, but they will reply to a founder's one-to-one.
— Jen AbelThe first call decides whether you get information later
The intro call is the most important of all calls: it sets how the other side sees you, how they respect your role, and how much they're willing to tell you. Jen's approach is extremely informal — no demo, no slides, a 30-minute one-on-one conversation where the other person talks first. She stresses not bringing a recording device and not recording: the other person won't open up, won't show weakness. Once you enter a formal sales process, they clam up, so the information advantage lives entirely in that first call.
— Jen AbelThe best sellers aren't the ones who were trained
Jen says enterprise sales is brutally hard to hire for, because the more someone has been trained in sales, the less natural they are. The most successful sellers are not trained sellers, which is also why founders are underrated at this: they're bad at running a process, but good at digging for information, following a thread with follow-up questions, and firing people up with a vision. Her numbers: two or three of every four calls have something real in them, and roughly a quarter should be actively walked away from because the maturity gap between the two sides is too wide — fast disqualification is itself part of the job.
— Jen AbelThe demo is the carrot, you can't just hand it over
Most people's stages are intro, demo, proposal, contracting, close, and they jump straight from the intro call to the demo. Jen says the demo is the carrot in the process, and before giving it you must hold another 15-minute meeting with the champion: confirm whether the right people will be there and what you should show. She'll ask the other person to ask a specific question on her behalf during the real demo, so they leave their fingerprints on the solution. That way the demo is built together with the internal executive, and competitors won't do those extra steps.
— Jen AbelA demo you're pulled into as a checkbox is already lost
The worst case is doing a demo straight at four or five strangers, especially when they say "we're doing due diligence and want to see what you've built" — Jen says don't go. One, you become a checkbox; two, you perform the whole product with zero competitive intelligence, and at that moment the deal is already gone. The target state for an enterprise deal is making the other side feel "this seems made specifically for me." Her pacing: the whole thing should fit inside a 90-day sales cycle, depending on the other side's maturity.
— Jen AbelDemo only 20% of the product
Jen's rule: 80% of a product's value comes from 20% of its features, and that 20% is what you asked about in the earlier calls. Don't demo the whole product — once you show a feature the customer won't use, they'll say on the spot "I won't use this, or that," and the tight narrative you spent weeks building gets dismantled. She's seen enterprise customers say outright: I don't want to pay this much for a tool half of which I won't use. The demo is project management and narrative control combined, not a feature tour.
— Jen AbelA win rate above 35% means you're priced too low
A healthy enterprise win rate isn't 50%, it's 25% to 35% (qualified lead to signed). Jen's judgment: if your win rate is above that range, your price is too low. Because the market talks to itself — the worst case is quoting 50 to one person's friend and 500K to another. She also notes that roughly another 25% of the deals you lose will boomerang back within a year.
— Jen AbelIn their own words · checked verbatim
you don't want to be too pointed of like anchoring them towards your product because again the more they speak you can start to like pull on the strings that matter
Jen Abel21:39
the fastest way to commoditize yourself is to go into some sales script, like budget, authority, need, timing. That should be in the back of your brain. You never actually ask those questions.
Jen Abel26:52
The whole game is to slow down to go fast.
Jen Abel37:13
And then when you demo the product, 80% of the value comes from 20% of the product.
Jen Abel41:22
There's always someone in the organization that's gonna kill a deal. There's always somebody.
Jen Abel47:32
If your win rate is higher than that, your price is too low.
Jen Abel1:08:21
Services is still the largest line item in budgets.
Jen Abel1:18:33
you are a liability not closing this gap
Jen Abel1:20:40
Figures
| Enterprise win rate | Usually 30% to 35%; above that number means you're priced too low | 0:00 |
| Number of steps in the sales process | Most people think 5 steps, it's actually close to 15 | 2:02 |
| Intro call length | A 30-minute one-on-one conversation | 19:33 |
| Prep call with the champion before the demo | 15 minutes | 31:07 |
| Healthy enterprise win rate (qualified lead to signed) | 25%-35% | 1:08:21 |
| Success rate benchmark after a pilot | 80% | 1:11:27 |
| Share of lost deals that boomerang back within a year | About 25% | 1:09:21 |
| Recommended pilot length | 2-3 days | 49:33 |
| Number of enterprise customers (the stage where the founder needs to be present in person) | The first 10 | 1:18:33 |
| Number of open roles at State Affairs | Multiple | 1:23:45 |
Glossary
- N minus one
- The executive one level below the decision maker, usually the person actually pushing the budget.
- pincer model
- The founder works from the very top and the AE works from N minus one, pushing both sides at once.
- champion
- Someone inside the customer who is willing to push the project for you and help you get aligned.
- disqualify
- Deciding the other side isn't mature enough and actively walking away from the deal.
- ARR
- Annual Recurring Revenue, the metric subscription companies watch most closely.
How to listen
Founders and early sales leads who are landing or about to land enterprise deals, especially teams with $100K+ ACVs whose deals keep stalling at demo or procurement.
The recruiting pitch at the end, at 1:23:45, can be skipped.