Builds a founder-led B2B sales motion - ICP and kill criteria, outbound message, first-call and demo plan, pilot and procurement plan, pipeline math, and a readiness check for your first sales hire. Use when you ask about founder-led sales, enterprise sales, cold outreach, ICP, 'why are deals stalling', pilots/POCs, procurement, 'when do I hire a sales rep', or adding sales to a PLG product. Draws on 49 Lenny's Podcast guests incl. Jen Abel, Geoffrey Moore and Pete Kazanjy.
80
100%
Does it follow best practices?
Run evals on this skill
Adds up to 20 points to the overall score
Low
Low-risk findings worth noting

Turns 'we need to start selling' into a written motion: who to sell to, what to say, how to run each call, and when to hand it off. Built from 237 insights from 49 Lenny's Podcast guests. Lead team: Jen Abel, Geoffrey Moore, Pete Kazanjy.
If the user attached a deck, CRM export, call transcripts, pitch or email sequence, read it first and infer answers. Otherwise ask at most these 4:
| If... (situation) | Use | From | Why |
|---|---|---|---|
| ICP is fuzzy, you say yes to anyone | Favorite-customer ICP + kill criteria + beachhead segment | Jonathan Lowenhar, Pete Kazanjy, Geoffrey Moore | Wrong customer is the most expensive GTM mistake; one segment beats a match under a log |
| ACV about $100K+, exec must sign, no replies | Pincer (exec + N-1) + alpha pitch + manual 30-lead test | Jen Abel | Execs answer one-on-one, not marketing; 3 sentences, counterintuitive |
| Smaller ACV, outbound works somewhat | Cohorts of 10 first meetings + stage-conversion tracking | Pete Kazanjy | You learn per cohort instead of guessing after 100 sends |
| First call with an exec or N-1 | Informal intro call, no slides, ask what needs to change | Jen Abel | They clam up once it feels like a sales process |
| Chasm: early adopters done, pragmatists want references | Problem-first call, shut the laptop, one beachhead segment | Geoffrey Moore | Pragmatists buy what peers bought; lead with their problem |
| 10+ deals closed, you want a repeatable pitch | Setup + follow-through pitch with perfect-world criteria | April Dunford | Frames the decision so the champion can justify picking you |
| Demo is done, group is cold, pilot requested | Pre-demo call, demo the 20%, time-boxed pilot, POC as business case | Jen Abel, Madhavan Ramanujam | Deals are won on 'built for us'; pilots only run when the signing path is mapped |
| Buyer wants to buy but keeps stalling | JOLT: judge, recommend, limit exploration, take risk off | Matt Dixon, April Dunford | 56% of no-decision losses are fear of failure, and urgency makes it worse |
| First rep or SDR hire is on the table | Selling while loop: sell, extract, hire two, scale | Pete Kazanjy, Jason Lemkin | Do not hand off what you cannot yet repeat |
| Self-serve usage but no enterprise deals | PQA/PQL lead paths + admin and terms-page signals + pilot AE | Elena Verna | Usage without a buyer is not a lead |
Fill this in and paste it into your doc.
# Sales Motion Brief - <product>, <date>
## 1. Game and ICP
- Motion: <enterprise sales-led / SMB marketing-led / PLG+sales / hybrid>; initial ACV: <$>; cycle: <months>
- Beachhead segment: <one segment> | Compelling reason to buy: <severe, worsening problem>
- Account profile: <size, trigger> | Personas: user <>, evaluator <>, budget owner/signer <>
- Favorite customer: <name> | Kill criteria: 1) <> 2) <> 3) <>
## 2. Outbound
- Targets: <30 named accounts> | Exec: <> N-1: <>
- Message (<=3-4 sentences): <relevant / counterintuitive / problem-focused>
- Alpha line (what the exec says at the board meeting): <>
- Channels + owner: <email, LinkedIn, text intro, call>
## 3. Call plan
- Call 1 questions: what needs to change / how measured / why now / why not wait
- Disqualify if: <maturity gap signals>
- Pre-demo call asks: <> | Demo 20%: <3 moments tied to their priorities>
- Pilot: <length, users, 3 tasks, success criteria, paid/free> | Signing path: <procurement, security, legal, signer, expected days>
## 4. Pipeline math (per cohort of 10 first meetings)
| Stage | Target | Actual |
|---|---|---|
| First meeting -> second | ~70% | |
| -> third meeting | ~45% | |
| -> demo -> pilot | ~25% past demo | |
| -> won | 15-25% of first meetings | |
Top 3 loss reasons (from lost-deal review, not rep opinion): <>
## 5. Handoff readiness
- At-bats so far: <n> | Win rate: <%> | Written assets: <slides, scripts, templates, objection list>
- Hire plan: <2 reps, ramp, first leads to best closer> | Founder keeps: <customer contact for product R&D>
## Next 3 actions
1. <this week> 2. <this week> 3. <next 2 weeks>Score each 1-5 for the user's pitch, outreach, pipeline or sales plan.
| Criterion | 1 | 3 | 5 |
|---|---|---|---|
| ICP and kill criteria | 'Anyone with the problem'; no refusals | Account profile only | Account plus personas, favorite-customer evidence, written kill criteria (Lowenhar, Kazanjy) |
| Outbound message | Generic, feature-led, long | Role-relevant but problem-generic | 3-4 sentences, counterintuitive, exec-level alpha, tested on 30 leads (Abel) |
| Discovery / first call | Script or BANT questions, demo on call 1 | Open questions, no change/urgency probing | Informal, change-focused, books call 2, asks for the no (Abel, Moore) |
| Pitch and demo | Feature tour of every screen | Value-led but generic | Setup + perfect-world criteria, demo the 20%, proof, objections, ask (Dunford, Abel) |
| Stakeholder and deal control | Single contact, email-only | Champion identified | Champion armed, exec and N-1 engaged, skeptic debrief, signer and procurement path mapped (Abel, Dunford) |
| Pilot and close | Free open-ended pilot, work starts pre-signature | Pilot with a goal | Time-boxed, co-authored success criteria, ROI inputs agreed, Word-doc paper, signer known (Abel, Ramanujam) |
| Pipeline instrumentation | Only closed revenue | Stage counts | Cohorts of 10, stage conversion, lost-deal review against rep stories (Kazanjy, Lemkin, Grosser) |
| Handoff readiness | Hiring on gut | Some docs | 15-25% win rate over 50-100 at-bats, extracted assets, two-rep A/B plan (Kazanjy, Lemkin) |
| Output: score per criterion, total out of 40, then the top 3 fixes (lowest scores first), each with the guest or framework behind it and a rewritten example. |
references/frameworks.md - every framework in this skill, how to run itreferences/quotes.md - verified quotes with timestampsposition - hand off when the pitch fails because the category, alternatives or differentiated value are unclearprice - hand off for POC pricing, packaging and willingness-to-pay before the commercial conversationcustomer-interviews - hand off when you need discovery on problems before you have anything to sellhire - hand off to build the scorecard and interview loop for the first sellermenkesu/awesome-pm-skills
c1b6e2d
If you maintain this skill, you can claim it as your own. Once claimed, you can manage eval scenarios, bundle related skills, attach documentation or rules, and ensure cross-agent compatibility.