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enterprise-sales

refoundai/lenny-skills

Navigate enterprise sales using frameworks from 9 product leaders who closed large deals at Stripe, Superhuman, and beyond.

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What is enterprise-sales?

This skill helps you close enterprise deals by identifying buying committee dynamics, overcoming customer indecision, and navigating procurement. Use it when managing complex sales cycles, handling multiple stakeholders, or converting product-led users to enterprise contracts.

Identify sales stage and map the buying committee to find champions and economic buyers
Address customer fear of messing up (FOMU) rather than relying solely on urgency
Guide procurement navigation by proactively handling administrative and compliance requirements
Frame proof-of-concepts as collaborative business case exercises, not product demos
Build conservative, achievable business cases that set you up to over-deliver
De-risk deals using the JOLT method: Judge indecision, Offer recommendation, Limit exploration, Take risk off the table

How to install enterprise-sales

npx skills add https://github.com/refoundai/lenny-skills --skill enterprise-sales

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How to use enterprise-sales

1.When a user describes an enterprise sales challenge, identify which stage they're in: prospecting, discovery, procurement, or closing
2.Map the buying committee by asking who the champion, economic buyer, and other key stakeholders are
3.Diagnose the real blocker: Is it indecision, fear of messing up, or procurement friction?
4.Apply the relevant framework: JOLT for indecision, champion-arming for committee alignment, or proactive procurement handling
5.Help build or refine the business case using conservative numbers and collaborative POC design

Use cases

Good for

Closing a $500K+ SaaS deal with a 7-person buying committee across IT, Finance, and Operations
Converting a product-led user with strong adoption into an enterprise contract
Navigating a 6-month procurement process with legal and compliance requirements
Overcoming a stalled deal where the champion is afraid of being blamed for a bad decision
Building a business case for a POC that demonstrates clear ROI to the economic buyer

Who it's for

Enterprise account executives and sales leaders
Founders selling their first large deals
Product-led growth teams converting self-serve users to enterprise
Sales managers coaching reps through complex, multi-stakeholder cycles

enterprise-sales FAQ

What's the difference between FOMO and FOMU?

FOMO (Fear of Missing Out) is about missing an opportunity. FOMU (Fear of Messing Up) is about being blamed for a bad decision. Most enterprise deals stall because of FOMU—buyers fear the reputational risk of choosing wrong, not because they don't want the product.

How do I identify the champion in a buying committee?

The champion is the person whose job is to get consensus across the committee and push the deal forward. They're typically not the economic buyer. Once identified, arm them with tailored materials for IT, Legal, Finance, and other stakeholders so they can advocate internally.

Should I run a POC or a demo?

A POC should be framed as a business case exercise, not a product demo. Work collaboratively with the buyer to build an ROI model and validate assumptions. This shifts the POC from a technical test to a shared business planning exercise.

How do I handle procurement without getting sidelined?

Proactively do the work for them. Provide the forms, compliance docs, and templates they need upfront. Don't wait for procurement to ask—make their job easy and you stay in control of the process.

What if the deal is stalled with no clear reason?

Use the JOLT method: Judge the level of indecision, Offer a firm recommendation on next steps, Limit exploration by building trust, and Take risk off the table by de-risking the decision (e.g., shorter contract, pilot pricing, or success guarantees).

Full instructions (SKILL.md)

Source of truth, from refoundai/lenny-skills.

name: enterprise-sales description: Help users navigate enterprise sales. Use when someone is closing large deals, managing complex buying committees, handling procurement, or converting PLG users to enterprise contracts.

Enterprise Sales

Help the user navigate enterprise sales using frameworks from 9 product leaders who have closed large enterprise deals at companies from Stripe to Superhuman.

How to Help

When the user asks for help with enterprise sales:

Identify the stage - Determine if they're prospecting, in discovery, navigating procurement, or closing
Map the buying committee - Help them identify the champion, economic buyer, and other stakeholders
Address indecision - Focus on overcoming customer fear of messing up, not just building FOMO
Navigate procurement - Guide them through the administrative and compliance requirements

Core Principles

40-60% of deals die to indecision

Matt Dixon: "Our analysis showed that anywhere between 40 and 60% of the average salesperson's qualified pipelines will be ultimately marked as closed loss, no decision." Most deals are lost not to competitors, but to customer inertia and fear.

Identify and arm the champion

April Dunford: "Typically we have between five and seven people involved in what we call making the decision. By far the most important persona is what we call the champion - this person's job is to get consensus and champion the deal across everybody." Arm them with materials for IT, Legal, and the Economic Buyer.

FOMU beats FOMO

Matt Dixon: "The omission bias is the fact that people don't want to be blamed for making decisions that lead to a loss. People are okay with missing out. They are not okay with messing up and being blamed." Address Fear of Messing Up, not just Fear of Missing Out.

Make procurement's job easy

Jen Abel: "When you get to procurement, you're going to have to do all the work. Make their job easy. Give me the forms that you need to fill out. I'll fill them out for you." Proactively handle the administrative burden to avoid being sidelined.

POCs are for business cases, not demos

Madhavan Ramanujam: "The POC should be framed as the entire goal of the POC is to create a business case, period, full stop. It is not to demonstrate product functionality." Treat POCs as collaborative exercises to build ROI models.

PLG to enterprise is an escalator

Elena Verna: "Product-led sales converts the usage that you've generated via self-serve into a sales opportunity and it attaches a salesperson to close a much larger contract." Identify the escalator from individual use case to enterprise-level solution.

Under-promise, over-deliver

Matt Dixon: "What great salespeople do is they know that while they'll stand by those claims, they try to under-promise and over-deliver. Build your business case around a 5X improvement, then let's set up to over-deliver against that." Build cases around conservative, 100% achievable numbers.

Use the JOLT method

Matt Dixon outlines four steps to overcome indecision: Judge the level of indecision, Offer a firm recommendation, Limit exploration by building trust, Take risk off the table by de-risking the deal.

Questions to Help Users

"Who is the champion inside the account and what do they need to succeed?"
"What would cause this deal to die to 'no decision'?"
"What's the buyer's biggest fear about messing up?"
"Have you identified the final signatory and what they care about?"
"Are you building the business case collaboratively or presenting it?"
"What can you do to de-risk this decision for the buyer?"

Common Mistakes to Flag

Relying on FOMO alone - Dialing up urgency without addressing the fear of being blamed for failure
Ignoring the champion - Selling to the economic buyer directly instead of arming an internal advocate
Passive procurement - Waiting for buyers to navigate internal processes instead of doing it for them
Demo-focused POCs - Treating proof of concepts as technical tests instead of business case exercises
Best-case projections - Building business cases around optimistic numbers that set up for disappointment