The Complete Lenny Rachitsky Playbook : Prompts, Growth Frameworks, and Strategies - Part 2 of 2
Part 2 of Lenny Rachitsky Playbook shows how to Lennify your business with ready-made prompts, frameworks, workflows, Growth Loops, and GTM playbooks across content, marketing, sales, and product.
Imagine applying Lenny Rachitsky’s tactics directly into your team’s playbook.
This is the Part 2 of The Lenny's Playbook: Enterprise Edition – the follow-up to our deep dive into Lenny’s growth machine.
In case you missed Part 1, I broke down Lenny’s user growth timeline, content flywheels, and community engine. Here is the link.
The Lenny Rachitsky Playbook : Prompts, Growth Frameworks, and Strategies - Part 1 of 2
I didn’t plan to write a case study on Lenny.
In this part, I flip the script: how can your content, marketing, sales, product, and customer success teams replicate Lenny’s system?
We’ll cover practical prompts, plug-and-play workflows, quarterly OKRs, and internal GTM playbooks so you can “Lennify” your company’s growth engine.
In Part 1 we have covered:
The user and revenue growth timeline
Key inflection points
Content + Monetization: The Freemium - With Prompts
The Community Flywheel: Why People Stay (and Pay) - With Prompts
Ecosystem flywheel that makes Lenny’s business unstoppable - With Prompts
Use-case Prompts: Lennify your Business
In this part (Part 2) —we are gonna cover below:
The complete Enterprise Lennification Playbook (with prompts)
Plug-and-play workflows for founders, marketing, product, and customer success teams (with prompts)
Quarterly OKRs and KPIs to measure impact (with prompts)
Real-world use cases and templates (with prompts)
Bonus: How internal teams (Sales, CS, Enablement) can leverage this system to drive GTM (with prompts)
Let’s explore this tactical guide to scaling trust and value just like Lenny did – and that too at an enterprise scale.
The Complete Enterprise Lennification Playbook (with Prompts and Growth Frameworks)
Most founders try to scale with tactics.
Lenny scaled with trust systems.
This isn’t about becoming a creator.
This is about using content, community, and clarity as growth levers — just like Lenny, but at enterprise scale.
Here’s how to Lennify your company across 5 areas:
#1 Content → Trust Engine
If you want to know more about how Lenny actually used content flywheel, read Part 1. Link here…
Lenny's superpower? Teaching what others gate.
What to do:
Product managers → write playbooks
Founders → share how strategy decisions were made
Engineers → explain technical tradeoffs
CS leaders → break down onboarding wins
Prompts to use:
Use-Case 1:
“Build a Trust Engine: Turn Internal Docs into High-Impact Content”
Prompt:
“Your company already operates like a category leader internally—now it’s time to show the world how. As a founder focused on growth strategy and marketing, your content flywheel should start where trust is built: by sharing real internal artifacts that prove your team knows what it’s doing.
Ask your team leads this simple question:
‘What’s one internal doc we use weekly that, if shared, would make us look world-class?’
Look for living documents—used often, updated regularly, and rooted in real execution.
Then apply the Trust Engine filter:
- Is it actually used, not just a pretty template?
- Is it tactically useful to people in our space?
- Does it reflect clear thinking, smart tradeoffs, or operational excellence?
Examples by function:
-- Product: Decision frameworks, sprint rituals, roadmap docs with scoring criteria
-- Engineering: System tradeoff notes, architecture diagrams, code review principles
-- Founders: Strategic memos, investor updates, GTM pivots and rationale
-- CS/RevOps: Onboarding flows, renewal processes, success metrics dashboards
Once selected, convert it into a content flywheel:
1. Source post – Publish the core doc or a redacted version (blog, Notion, LinkedIn article)
2. Derivatives – Slice into threads, carousels, email drops, or video explainers
3. Narrative – Use the backstory in podcasts, founder storytelling, or investor decks
Done well, this single doc becomes a signal: you’re not just building — you’re building differently, and others can learn from you.”Use-Case 2:
“How We Improved [X KPI] by [Y%] — And How You Can Too”
Prompt:“You’re a founder leading growth and marketing. You’ve made a measurable improvement in a key KPI — now turn that win into trust-generating content that proves how you think, not just that you succeed.
Your goal: write a short, high-signal post titled:
‘How we improved [X KPI] by [Y%] — and how you can too’
This isn’t a case study. It’s a transparent debrief others can learn from. Keep it concise, tactical, and insight-rich.
Follow this outline:
1. Lead with the Win:Start with the headline result. Be specific and confident.
“We reduced churn in our self-serve segment by 21% in 45 days.”
2. Set the Scene (50 words):Describe the problem before the change. Add enough context for relevance.
“Our activation rate plateaued, especially for users coming from integrations. We noticed a 3-step drop-off.”
3. Explain What You Did (75–100 words):Break down the actions. Focus on 1–2 moves that mattered.
“We added an automated onboarding replay inside Slack. It gave teams a shared moment of value, which lifted collaborative usage by 32%.”
4. Call Out the Insight or Tradeoff:Share what surprised you or where it didn’t go as expected.
“We expected better results from the email nudge. Turns out, in-app timing was everything.”
5. Teach the Reader (50–75 words):Translate your win into something transferable.
“If you’re seeing activation friction, ask: ‘What’s the first moment a team, not a user, gets value?’ That shifted our whole approach.”#2 Newsletter → Owned Distribution
Lenny didn’t rely on social reach. He built direct connections through newsletter subscriptions.
What to do:
Start a weekly or bi-weekly newsletter written by a named team member
Feature customer tactics, product wins, internal breakdowns
Prompts to use:
Use-Case 1:
“Write This Week’s Newsletter in Lenny’s Tone: Casual, Tactical, No Fluff”
Prompt:You’re building a direct connection with your audience — just like Lenny did — not through social reach, but through a consistently valuable, personal newsletter. This isn’t corporate marketing. It’s 1:1 writing from a smart operator to peers.
Your goal: write this week’s issue in a voice that’s casual, tactical, and fluff-free — in the style of Lenny — using real company insights your audience can apply.
Start with this structure:
1. Hook (1–2 sentences)A blunt insight, surprising result, or pain point your audience will nod at.Example: “We almost gave up on onboarding emails — until this one change got a 58% reply rate.”
2. Context (2–3 sentences)Set the stage. Explain where this came from. What were you trying to solve?
3. Tactical Breakdown (3–5 bullets or short paragraphs)
Share exactly what you did, what worked, and what didn’t.
Use specifics, numbers, and screenshots/templates where possible.
Think: frameworks, message tests, small wins, dashboards, onboarding tweaks, decision memos.
4. Lesson or Playbook (1–2 sentences)Wrap with a takeaway the reader can steal or a question they should ask.“If you’re struggling with [X], try asking: what’s one small win that builds emotional momentum?”
Rotate content types weekly or bi-weekly:
- Customer tactic: “How one team used our product to cut time-to-value in half”
- Internal win: “How we fixed churn in our expansion segment — and what failed”
- Product breakdown: “Behind the scenes of our AI feature launch: tradeoffs + metrics”
- Founder POV: “What changed our minds on pricing last quarter — and what we’d do differently”
Make it sound like a person, not a company. Sign off with a name. Use humor sparingly, clarity always.Use-Case 2: “Turn a Product Launch into a Customer Use Case That Builds Trust”
Prompt:
You just launched a new feature or product update. Now turn that launch into a tactical, customer-first story your audience can apply — written in a casual, tactical, no-fluff tone (like Lenny).
The goal: make the launch useful to your audience by showing how someone actually used the feature, what they accomplished, and how the reader can do the same.
Use this format in your weekly or bi-weekly newsletter (written by a real team member), focused on customer tactics, product wins, or internal breakdowns.
Use-Case Newsletter Format
Subject/Title:
How [Team or Company] used [Feature] to [Achieve X] — and how you can too
1. Lead with the Win (1–2 sentences)Start with the customer outcome, not the feature.
“A customer success manager at [CustomerCo] cut ticket backlog by 42% using Smart Tags — without changing their support process.”
2. Set the Scene (2–3 sentences) What problem were they facing? Why was this hard before?
“Before this, they had a team of 4 manually reviewing incoming support requests and tagging issues by hand. It was slow and inconsistent.”
3. Break Down What Changed (3–5 bullets or short paras)Show how they used the feature in practice. Include configs, integrations, or key behaviors.
-- They connected Smart Tags to their Zendesk pipeline
-- Set up 4 auto-categorization rules based on NLP patterns
-- Routed high-priority issues straight to the lead CS rep
-- Within 2 days, they resolved 23% more urgent tickets
-- Customers even started noticing the faster responses
4. Highlight an Insight or TradeoffCall out what was surprising or nuanced.
“They actually turned off one automation because it triggered too often. Simpler rules worked better than complex ones.”
5. Teach the Reader (1–2 sentences)Wrap with a practical takeaway.
“If you're overwhelmed by inbound support noise, try tagging first by urgency — not issue type. It’s what gave this team leverage fast.”
6. Sign Off Keep it personal, name-driven, and consistent.
“— Jess, Product Marketing at [Your Company]”
Reuse Across Channels:
- Blog: expand into a full customer story
- Social: excerpt insights into threads
- Sales: turn into proof points or objection-handling material
- Success: include in onboarding or adoption sequences#3 Community → Retention & Moat
Lenny’s paid Slack group became his stickiest feature. You can do the same — with your customers.
What to do:
Start an invite-only community for your top 1% customers, partners, or users
Use it for AMAs, feedback loops, meetups, and support
Prompts to use:
Use-Case 1: “Who are 20 power users we can invite today to kickstart community behavior?”
Prompt:
You are a startup founder, product manager, marketer, or community lead looking to create a sticky, high-value community like Lenny's paid Slack group.
Write a strategic execution plan to launch an invite-only customer community designed to increase engagement, retention, feedback loops, and product stickiness.
First, identify the top 1% of users, customers, or partners based on criteria like engagement, LTV, feedback history, or advocacy. Include a method to segment and prioritize this group quickly.
Then, outline how to invite them into a private Slack (or equivalent) space with intentional positioning that communicates exclusivity, value, and purpose (e.g., early access, roadmap influence, AMAs, direct access to founders).
Include 3 types of recurring activities to build community behavior fast—such as:
- Weekly or monthly AMAs with team members or power users
- Live product feedback sessions
- “Office hours” or support circles
Incorporate two starter prompts:
“Who are 20 power users we can invite today to kickstart community behavior?”
“How can we immediately engage this group so they feel seen, heard, and valued?”
Emphasize psychological drivers like exclusivity, influence, and belonging to ensure initial traction. Detail what success looks like in the first 30 days (e.g., % active users, number of interactions, first feedback loop created).
Optional: Recommend tools, onboarding flows, or automation tips to reduce friction and scale.Follow-Up Prompt:
You’ve launched a curated, invite-only community of your top 1% users, customers, or partners. Now, develop a tactical engagement strategy to turn passive members into active contributors in the first 30 days.
Break the plan down into three key stages:
1. Onboarding Experience:
What should happen in the first 24–72 hours to drive immediate interaction?
Include onboarding messages, welcome rituals, and lightweight calls-to-action (e.g., introduce yourself, share your favorite use case).
Assign a “community concierge” or welcome guide role, even if automated.
2. Weekly Engagement Loops:
Suggest recurring content and events that drive habit formation.
Examples: Monday question threads, Friday wins, bi-weekly AMAs, “What’s one thing you shipped this week?” posts.
Use tagging and lightweight gamification to encourage replies.
3. Feedback & Recognition:
How do you make members feel heard, seen, and valued?
Include feedback prompts, polls, behind-the-scenes updates, and recognition of top contributors.
Design small “moments of delight” (e.g., early feature access, personal thank-yous, swag).
Bonus: Suggest a 5-minute daily routine the community manager or founder can run to keep the community warm and responsive.#4 Podcasts & Interviews → Trust at Scale
Lenny turned long-form interviews into weekly discovery machines.
What to do:
Start a podcast hosted by a founder, product lead, or customer
Interview internal experts or partner leaders
Repurpose the best 2-minute clips into shorts, emails, and LinkedIn posts
Prompts to use:
Use-case: “What 5 guests would our ICP be shocked we got access to?”
Prompt:
You are a founder, product lead, or marketer aiming to build a high-leverage discovery engine and brand asset—modeled after Lenny’s podcast—by launching a long-form interview series. Write a strategic plan for creating a weekly podcast or video interview format that serves both as a content flywheel and a discovery tool for product insights.
Begin by identifying your ideal host (founder, PM, or standout customer) and define why their voice carries authenticity, relevance, and narrative control. Then, generate a shortlist of 5 guests your ICP (ideal customer profile) would be shocked or excited to hear from—using the prompt:
“What 5 guests would our ICP be shocked we got access to?”
Outline the structure of a 30–45 minute episode designed to surface market insights, real stories, and memorable moments that can be clipped and repurposed. Include a bank of 5–7 recurring questions designed to:
- Elicit high-signal discovery insights
- Reveal behind-the-scenes decisions or lessons
- Speak to your ICP’s aspirations or fears
Detail your post-production repurposing workflow:
- How to extract the best 1–2 minute segments and turn them into short-form video, LinkedIn posts, and newsletter snippets
- How to templatize clip creation and distribution across your top 3 channels
- How to track engagement and feedback loops to inform future guests and episodes
Finally, include a launch checklist:
1. First 3 guests to secure
2. Episode template
3. Distribution plan
4. Content calendar for the first 4 weeksFollow-up Prompt:
You’ve recorded a long-form interview with a high-signal guest—now your goal is to pull out a 1-line hook that stops your ICP mid-scroll and makes them hit play on a short-form clip.
Write 5 variations of 1-sentence hooks that create instant curiosity, emotional pull, or surprise—based on one of your strongest 1–2 minute moments from the interview.
Use formulas like:
“Most [role]s get this completely wrong—here’s how to fix it.”
“We almost shut down the company because of this mistake.”
“Here’s how [famous brand] secretly builds [outcome].”
“This advice saved us 6 months of wasted work.”
“Nobody tells early-stage teams this—but it changes everything.”
Make each hook specific, emotionally charged, and relevant to your ICP’s fears, goals, or hidden questions.
Optional: Include a before/after or myth vs. reality angle.#5 Job Boards, Summits, Ecosystem Growth Loops
Lenny turned his audience into a talent collective, an event brand, and a recruiting channel.
What to do:
Launch a lightweight job board for your industry
Host a summit with your best customers as speakers
Build internal tools → open source → growth engine
Prompts to use:
Use-case: “What’s one internal tool our users would pay for or share if we released it?”
Prompt:
You are a founder, product leader, or marketer looking to turn your audience into a full-stack growth ecosystem—like Lenny did—with a lightweight job board, a customer-led summit, and open-sourcing internal tools.
Create a strategic execution plan that includes:
1. Launching a Niche Job Board
Define the niche (e.g., “product roles at early-stage AI startups”) your audience deeply cares about.
Detail the fastest way to spin it up (e.g., Pallet, Webflow + Airtable, Notion).
Include outreach templates to get the first 10 high-signal jobs listed.
Explain how to seed initial traction through newsletter drops or Slack channels.
2. Hosting a Community-Led Summit
Outline how to structure a virtual or in-person summit where your best customers or partners are the featured speakers—not your company.
Include speaker criteria, outreach tactics, and suggested topics that speak to your ICP’s real-world problems.
Recommend a format (e.g., “20-minute lightning talks,” “panel of operators”) that maximizes insight over fluff.
Suggest promotional channels to drive attendance and create post-event content loops.
3. Open-Sourcing Internal Tools as Growth Assets
Use the prompt:
“What’s one internal tool our users would pay for or share if we released it?”
Brainstorm 3-5 candidates (e.g., internal dashboards, scripts, checklists, frameworks) that could be productized.
Detail the minimum work needed to polish and release one as open source or as a free utility.
Include the downstream value: backlinks, social shares, community engagement, SEO lift.
Wrap it all into a 90-day roadmap that shows how these 3 assets can compound over time into a branded ecosystem that attracts talent, builds authority, and fuels product growth.Follow-up Prompt:
You’ve identified your top 100 most loyal, vocal, or high-impact users. Now design an event experience that feels like a reunion—deeply familiar, high-trust, and high-signal.
Write a plan that answers:
- What format would make this feel intimate but high-value? (e.g., retreat, digital roundtable, mini unconference, regional meetup)
- What rituals or moments could recreate shared history, insider status, or early journey vibes? (e.g., “OG user” badges, feature throwbacks, live roadmap co-creation)
- What would make attendees say, “I can’t believe they included me in this”?
Include ideas for:
1. Surprise and delight elements (swag, shout-outs, personalized thank-yous)
2. Collaborative experiences (workshops, story share-outs, “build with us” sessions)
3. Post-event rituals that keep momentum going (e.g., highlight reel, private Slack thread, exclusive drop)
Bonus: Include 2–3 name ideas for the event that reflect community roots and elevate status.Lenny didn’t “do content.”
He built leverage.
The Lennification playbook isn’t about personality. It’s about repeatable systems for earning trust and distributing value.
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Plug-and-play workflows for founders, marketing, product, and customer success teams (with prompts and growth loops)
Lenny’s success wasn’t just content. It was a process — consistent, clear, compounding.
Here’s how to install Lenny-style workflows inside your company — just templates + prompts that work across teams.
For Startup Founders
Goal: Build trust at scale, shape the narrative, and attract community and talent.
Weekly Workflow:
Publish 1 founder memo per week (lesson, story, internal decision)
Turn that into a LinkedIn post + internal email
Drop it into community or company Slack
Prompts:
“Write a memo called: ‘Why we changed our pricing — and what we learned.’”“Break down a big mistake you made as a founder. Turn it into a 3-step framework.”“What’s one unpopular truth about your market you believe deeply?”For Marketing / GTM Teams
Goal: Drive demand through value-first content and owned media — not paid noise.
Weekly Workflow:
Turn internal wins into blog posts or case studies
Repurpose each into 3 social posts, 1 email, 1 downloadable asset
Feature customers as teachers, not testimonials
Prompts:
“Turn our onboarding workflow into a public Notion doc with commentary.”“Write: ‘How [Customer] increased demo-to-close by 24% using our playbook.’”“What’s a trend in our space we don’t agree with? Write a POV post on it.”For Product / Product Management Teams
Goal: Humanize roadmaps, amplify changelogs, and create feature-market resonance.
Bi-weekly Workflow:
Write a “Why we built this” post for every new feature
Record a 3-min internal Loom explaining tradeoffs
Share customer use cases in the next update
Prompts:
“Write a changelog that starts with a user quote, not a bullet list.”“Create a post titled: ‘3 ways to use [new feature] to reduce ops friction.’”“Interview one customer about how they used [feature] differently than we expected.”For Customer Success Teams
Goal: Turn support insights into scalable education and evangelism.
Monthly Workflow:
Capture 3 “customer wins” and convert them into posts, decks, or how-tos
Run an AMA or live session inside the community
Share 1 new idea from users back to product
Prompts:
“What’s a hack our best customers keep doing that we haven’t documented yet?”“Write: ‘3 ways our customers saved time this month (and how you can too).’”“Create a 1-pager called: ‘How to make your first 30 days with us count.’”Why This Works
Founders inspire trust →
Marketing attracts attention →
Product turns updates into growth →
CS drives usage →
All of it → loops into content, community, and activation.
This is how you operationalize Lennification across your company.
Quarterly OKRs and KPIs to measure impact (with prompts) - For Newsletters, Startups, and Businesses
Lenny didn’t build a brand. He built systems that compound.
To apply this in a company, you need clarity + accountability.
Here’s how to measure whether your team is actually Lennifying — or just creating more content noise.
Company-Wide “Lennification” Objective (Playbook inspired from Lenny Rachitsky)
Objective:
Build a scalable trust engine through value-first content, community, and product storytelling.
Founder / CEO
KR1: Publish 6 high-signal founder memos or essays this quarter
KR2: Drive 10,000 new newsletter subscribers from founder-led content
KR3: Join or host 3 public AMAs or podcasts to humanize the company voice
Prompt:
“What story, framework, or mistake would make my dream customer say: ‘This founder gets it’?”Marketing
KR1: Launch 1 new owned content format (e.g. podcast, teardown, tactical guide)
KR2: Repurpose every weekly post into 3+ social assets
KR3: Achieve 20% subscriber-to-customer conversion from newsletter funnel
Prompt:
“What’s the one resource we could give away right now that would save our audience time or stress — and build immediate trust?”Product
KR1: Publish 3 “Why we built this” breakdowns for new features
KR2: Increase product feature engagement by 15% through user stories and tutorials
KR3: Source 5 product roadmap inputs directly from the customer community
Prompt:
“What’s one customer quote or insight that would make someone want to use this feature?”Customer Success / Community
KR1: Host 2 customer-led AMAs or playbook sharing sessions
KR2: Launch or grow an invite-only community to 250 engaged members
KR3: Publish 5 customer use cases or “quick wins” from support data
Prompt:
“What’s one small win that a user had — that 100 others would benefit from seeing in action?”Final Prompt to Ask Your Team This Quarter:
“If Lenny ran our startup tomorrow, what would he stop doing, double down on, and build next?”If you’re into prompts, frameworks, and growth breakdowns — I share a fresh one every week
Real-world use cases and templates (with prompts) - Founder-led Growth like Lenny Rachitsky
Let’s bring Lennification to life.
These aren’t just ideas — they’re real, repeatable moves used by high-growth teams.
Below are real-world use cases with plug-and-play templates and prompts you can adapt instantly.
Use Case: Product Launch = Trust Magnet
Turn product updates into high-retention growth content.
Template:
"Why We Built This: [Feature Name]"
Problem it solves
Why now?
Internal debates + tradeoffs
How early customers are using it
What’s next
Prompt:
“What’s one feature we shipped that deserves a story — not a sentence?”Use Case: Newsletter as a Flywheel Anchor
Turn weekly emails into your highest-leverage asset.
Template:
“Weekly Tactic Drop” (3-min reads)
1 quick win
1 customer hack
1 open loop (something to reply to or share)
Light CTA (not a hard sell)
Prompt:
“If our newsletter wasn’t about us, but about making our customers look smarter at work, what would it say?”Use Case: Community-Driven Content
Let users become the content engine.
Template:
“Customer Play of the Week” Thread
Quote or screenshot from the customer
What problem it solved
Their workflow
Bonus tip or unexpected result
Prompt:
“Which user Slack message, support ticket, or feedback thread could be turned into a playbook?”Use Case: Founder Memo → Growth Catalyst
Build credibility and narrative authority.
Template:
“From the Founder: [Hard Decision We Made and Why]”
Context
Options we considered
Why we chose this
What we learned
Ask for feedback
Prompt:
“What uncomfortable but important decision did we make recently that the market would respect if we explained it?”Use Case: Case Study = Sales Enablement
Lenny-style teardown instead of dry decks.
Template:
“How [Company] Solved [Pain] Using [Feature]”
Problem
Setup
What changed
Outcomes (quantified)
Quote
Visual (workflow / result)
Prompt:
“Which recent customer success story would make our prospect say, ‘I want that outcome too’?”Pro Tip: Use these across:
✅ Email newsletters
✅ Sales outreach
✅ Product onboarding
✅ Internal enablement
✅ LinkedIn / X / Slack community
Final Prompt:
“If we did nothing else for the next 30 days but published one template, one story, and one tactic every week — what would those be?”Bonus: How internal teams (Sales, CS, Enablement, Funnel, B2B Growth) can leverage this system to drive GTM (with prompts)
Lenny didn’t just write great content. He made it useful — for education, trust, and action.
That’s exactly what internal GTM teams can do with his system:
educate prospects, activate users, and enable deals — using content as fuel.
For Sales Teams (AI Prompts for Funnel Enablement)
Use the system to warm leads, close deals, and build thought-leader credibility.
Tactics:
Share Lenny-style case studies before demos (“Here’s how one customer solved X”)
Use founder memos as credibility builders during long sales cycles
Quote community conversations to handle objections (“Others had the same hesitation — here’s what they did.”)
Prompts:
“What’s a high-signal article we can send instead of a cold pitch?”“What community conversation or quote can we turn into a deal-closing story?”“Which product feature post can replace a long capabilities deck?”For Customer Success Teams (To maintain ARR)
Use the system to onboard faster, deepen retention, and expand accounts.
Tactics:
Turn every customer success story into an internal case study
Use newsletters and product breakdowns as onboarding material
Share "customer play of the week" posts to encourage adoption
Prompts:
“What’s a customer win we haven’t turned into a playbook yet?”“Which Lenny-style blog post would help reduce new user confusion this week?”“How can we show a user they’re underutilizing us — and what’s possible?”For Enablement Teams (Build playbooks and templates)
Use the system to upskill reps with less fluff and more real context.
Tactics:
Create a “Lenny-style learning library” of internal tactics and best practices
Repurpose blog content and changelogs into talk tracks and battle cards
Use product posts as mini-training modules
Prompts:
“What internal doc should we rewrite in a Lenny format so people actually use it?”“What’s one tactic the top 10% of reps use that we can turn into a short internal guide?”“Which recent customer objection should become a teardown training email?”Cross-Team Flywheel Example
Product posts a feature breakdown.
Marketing repackages it into a newsletter.
Sales uses it in outreach.
CS turns it into a how-to for onboarding.
Enablement trains the team on it.
Final Prompt:
“What’s one story we’re underusing across sales, CS, marketing, and enablement — and how do we make it our next GTM asset?”Conclusion
Lenny’s success wasn’t just about writing – it was about building a repeatable trust engine that any team can run.
In this two-part playbook, we’ve seen how content, community, and clarity became Lenny’s unfair advantage, and exactly how you can embed those same practices across your organization.
The takeaway from Part 2 is clear: you don’t need to be a famous newsletter author to harness Lenny’s system – you just need the right processes. By applying these prompts, workflows, and OKRs in your day-to-day operations, you’re effectively “Lennifying” your enterprise, turning every department into a compounding growth driver.
Put these ideas into action – challenge your teams with the prompts, adopt the workflows, measure the impact, and iterate. The Lenny Rachitsky Playbook is no longer just Lenny’s secret sauce; it’s a blueprint for any company that wants to build credibility, community, and momentum at scale.
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