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Help users build a robust enterprise sales engine by mastering founder-led discovery, navigating complex procurement cycles, and designing products that meet organizational governance needs.
Passed 21 of 22 test cases with the skill, and 16 of 22 without it.
and 5 more in the full report
5 fixed16 passed either way1 still failing0 broke
Tokens, turns and time describe resource use, not a dollar price.
One of 5 test cases the skill fixed. Same model, same prompt, with and without the skill.
We keep getting late-stage stalls in our enterprise sales cycles, where prospects seem excited during initial demos but suddenly freeze before signing. Please evaluate our approach and provide a restructured discovery pitch outline along with a checklist to identify and resolve underlying buyer risk and hesitation.
| Checked | Without skill | With skill |
|---|---|---|
| Recommends addressing fear of messing up (FOMU) rather than escalating FOMO or urgency tactics. | Missed | Passed |
| Incorporates a dual-track product narrative that covers governance requirements alongside end-user utility. | Missed | Passed |
| Advises leading discovery calls with vulnerability by acknowledging startup stage to lower prospect defenses. | Missed | Passed |
The instructions your model reads when the skill loads.
Transition from founder-led sales to a repeatable, scalable enterprise engine.
Help the user with mastering enterprise sales motion using insights from 16 guests and posts across Lenny's Podcast and Newsletter.
Aparna Chennapragada: "In consumer, you're kind of like, 'Oh, we have a playbook for make the product work or make the feature work and make it delightful,' but I think in the enterprise, you almost have... Every time you think you have one use case, you have really two, which is how do you make sure that the feature works well and there's governance of the feature."
Every feature must satisfy two use cases: the functional user experience for delight and the organizational governance requirements for compliance.
Geoffrey Moore: "So in other words, they're on the same side. After the chasm, they say, 'I'm not sure about that, but we need what you have.' So transitioning from, 'We believe what you believe,' which is how you sell to visionaries to, 'We need what you have,' which is how you sell to pragmatists. That's the shift."
Transition your narrative from selling a shared vision to providing a concrete, repeatable solution that solves specific problems for pragmatic buyers.
Jeanne Grosser: "The experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the merchant. And so then you really want to create a customer buying journey that feels like very unique experiences."
Orchestrate every customer-facing function with the same level of intentional design and unique journey mapping as your core product.
Jason M Lemkin: "I think as soon as you've got those 10 customers and more than 20% of your time is booked up with customers, you need leverage. You need leverage."
Founders should personally close at least 10 to 20 customers who have no previous affiliation before seeking to hire sales help.
Jen Abel: "You need to be vulnerable. I would be very open and honest with where you are. Hey, I'm an early stage startup. We have a lot to learn. Can we kind of gain your insight into how this problem is manifesting on your side?"
Lower a prospect's guard by honestly acknowledging your startup status, encouraging them to share deeper pain points.
test cases passed, vs 16 / 22 without
More skills from the same source and nearby in the registry, with their headline benchmark lift.