​The GTM Playbook for Building a $300M+ ARR Business: Lessons from ClickUp’s COO

Here is some easy reading for Friday 🙂

Many startups copy other companies’ strategies without knowing if they fit their own market or customer type. This leads to wasted resources, stalled growth, and missed opportunities.

Scaling from $1M to $300M+ ARR isn’t about finding shortcuts. It’s about knowing your place in the LTV (customer lifetime value) and TAM (total addressable market) matrix and picking the right playbook.

If you don’t understand whether you’re whale hunting (few, high-value customers) or casting a wide net (many, low-value customers), you’ll waste effort on the wrong channels.

ClickUp’s growth came from refusing false choices like “PLG vs sales-led” or “brand vs demand gen.”

Instead, they run dual engines: PLG brings scale, while sales-led expansion boosts LTV by 11x.

They also treat growth like a portfolio with 70% proven bets, 20% smaller tests, and 10% big swings. This creates predictable growth while leaving room for breakthroughs.

They prioritize channels that compound (SEO, community, viral features) over ones with diminishing returns (ads, outbound). Constant reinvention is critical: what works at $10M won’t work at $100M.

Finally, they bake AI into 80% of revenue functions, from AI SDRs to content production, multiplying velocity and scale.

Key takeaways

Map your business on the LTV vs TAM matrix before setting GTM plans Run both PLG and sales-led engines if possible – let them feed each other Use a 70-20-10 allocation: proven bets, small tests, bold experiments Double down on compounding channels even if they take time to grow Avoid comfort zones – challenge your team to find new distribution wins Audit where AI can remove bottlenecks in your revenue machine Stop copying others blindly – only learn from businesses in your quadrant

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