How to scale from startup to $300,000,000+ ARR by mastering the fundamentals of go-to-market strategy
Building a billion-dollar B2B business isn’t about finding secret hacks or silver bullets. They don’t last or scale. It’s about mastering fundamental principles and being willing to reinvent yourself every six months to a year as you scale. Gaurav Agarwal, COO of ClickUp came to SaaStr Annual + AI Summit to share how they did it — and keep doing it.
As someone responsible for “all things money” at ClickUp – sales, marketing, growth, pre-sales, and post-sales – Gaurav has lived through the reality that what gets you to $1M ARR is completely different from what gets you to $10M, $50M, $100M, $300M and beyond. Nothing scales infinitely, and every stage requires its own playbook.
Here are the key principles that have driven ClickUp’s remarkable growth:
1. Know Where You Win: The LTV vs. TAM Matrix
Most companies fail because they try to adapt everyone else’s strategies without understanding their own fundamental positioning. Before you copy anyone’s playbook, you need to map your business on a simple 2×2 matrix:
- X-axis: Customer Lifetime Value (LTV) – How much can you make from your customers?
- Y-axis: Total Addressable Market (TAM) – How many customers are out there?
This creates four distinct quadrants, each requiring completely different go-to-market strategies:
High LTV, Small TAM: Whale Hunting You’re selling to Fortune 500 companies with limited prospects. Your channels must be high-touch: field marketing, trade shows, conferences, and business development. You can afford expensive customer acquisition because deal sizes justify the investment.
Low LTV, Large TAM: Cast a Wide Net You can’t afford expensive acquisition channels. Focus on organic growth: content marketing, SEO, social strategies, and community building. You need LTV-to-CAC positive channels that scale efficiently.
Low LTV, Small TAM: Exit Strategy If you have few customers who don’t pay much, you shouldn’t be in this business. Run away and find a better opportunity.
High LTV, Large TAM: The Sweet Spot This is where ClickUp operates, and it’s the most exciting quadrant. You can make almost any channel work – enterprise sales teams, billboards, TV ads, digital marketing. The world is your oyster for distribution strategies.
2. Learn From the Best-in-Class Across Industries
Don’t limit yourself to studying companies in your vertical. The best growth strategies often come from unexpected sources:
- For SEO: Study HubSpot, but also look at NerdWallet, Canva, and Zapier
- For brand building: Don’t just look at B2B companies – examine what Liquid Death and Beats by Dr. Dre accomplished
- For viral growth: Understand how consumer companies create shareability
At ClickUp, teams obsess over these best-in-class companies and adapt their learnings regardless of industry. A B2B company can absolutely learn from B2C growth tactics, because all customers are ultimately humans with similar psychological triggers.
3. Avoid Zero-Sum Thinking
The biggest mistake scaling companies make is creating false either/or narratives:
- Product-led growth vs. sales-led growth – Why not both?
- Brand building vs. demand generation – They should work together
- B2B vs. B2C tactics – Customers are humans regardless of context
ClickUp runs a dual-engine growth model that proves these approaches can be complementary:
Product-Led Growth Engine: Focuses on users – acquire, activate, monetize, and expand. This gives ClickUp distribution at scale and catches a wide net of prospects.
Sales-Led Growth Engine: Focuses on accounts where PLG has already landed users. The goal is reaching out to existing customers to drive expansion and deeper penetration.
The results speak for themselves: when a customer moves from self-serve/PLG to sales-assisted, ClickUp sees an 11x lift in LTV. Product-led growth provides the distribution; sales-led growth maximizes the lifetime value.
Most companies kill one motion in favor of the other, missing the massive opportunity of letting them feed into each other.
4. Master Your Growth Portfolio
As you scale, you need to think like a portfolio manager. Your growth strategy should diversify across multiple bets – channels, segments, products, geographies – each with different risk/reward profiles.
The 70-20-10 Resource Allocation Framework:
- 70% on proven channels with high probability of success
- 20% on small bets that deliver incremental gains
- 10% on big bets like viral content or breakthrough strategies that could create inflection points
This approach delivers predictable growth with asymmetric upside. The 70% gives you financial predictability, while the 20% and 10% create opportunities for breakthrough growth moments.
Key Portfolio Principles:
Understand Risk vs. Reward: Higher risk channels might extend payback from 20 to 50 months, while optimizing for quick payback could limit top-line growth. Find the efficient frontier.
Not All Channels Are Equally Repeatable: ClickUp can predict which SDR will hit their number and the ROI of Google branded search, but can’t predict which social media clip will get 50 million views. Plan accordingly.
Channels Have Capacity Limits: After hiring 100 account executives, productivity per rep declines. Most paid channels hit diminishing returns, but some organic channels compound infinitely.
5. Identify Compounding vs. Diminishing Channels
Understanding which channels scale versus which hit walls is crucial for long-term success:
Diminishing Return Channels:
- Paid advertising (Google, Facebook, etc.)
- Outbound sales beyond optimal team size
- Most performance marketing channels
Compounding Channels:
- Community: Takes time to build but becomes self-sustaining
- SEO/Content: High domain authority compounds with each new piece
- Viral Product Features: Like Slack or Dropbox, usage drives sharing
- Network Effects: Value increases with each new user
While you can’t scale Google paid search infinitely, you can scale Google organic content indefinitely with the right content engine.
6. Never Assume You’ve “Made It”
At $10M ARR, getting to $15M feels relatively easy. At $500M ARR, growing 50% to $750M is “extremely, extremely hard.” The only way to beat this challenge is maintaining hunger and assuming there are always better opportunities you haven’t discovered yet.
Combat the Local Maximum Trap: Teams often get stuck optimizing their current approach instead of finding breakthrough strategies. Always assume better distribution tactics and motions exist.
Apply Constant Pressure: Challenge yourself and your team to keep uncovering new ground. The moment you get comfortable is when competitors start gaining ground.
7. Leverage AI for 10x Velocity Gains
If you view revenue generation as a complex machine, AI creates opportunities to optimize efficiency at multiple steps simultaneously. Companies not using AI to accelerate their go-to-market motion will be left behind.
ClickUp’s AI-First Approach Across 80% of Revenue Functions:
- AI SDR: Automatically reaches out to form submissions, generated $1M in pipeline in the first month
- Content at Scale: Produces 40,000 pages monthly using AI, localized in 15 languages, resulting in 10x search impression volume
- Customer Support: AI chat agents resolve issues faster, freeing human agents for proactive account management
The key is systematically identifying every step in your revenue machine and asking: “How can AI increase throughput here?”
The Top Scaling Mistakes to Avoid (According to Gaurav)
Based on his experience scaling ClickUp to nine-figure ARR, Gaurav identified the most common and costly mistakes he sees companies make:
1. Misunderstanding Your LTV/TAM Position and Copying Wrong Strategies
The Mistake: Companies blindly copy successful strategies from other businesses without understanding whether they operate in the same LTV/TAM quadrant. A high-LTV, small-TAM business trying to use Canva’s mass-market SEO strategy will waste massive resources.
The Fix: Map your business honestly on the LTV/TAM matrix first, then only study companies in your quadrant. A whale hunting business should learn from enterprise software companies, not consumer apps.
2. Creating False Either/Or Choices
The Mistake: Forcing zero-sum decisions between complementary strategies. “We’re PLG, so we can’t do sales-led.” “We’re B2B, so we can’t use B2C tactics.” “We focus on demand gen, not brand building.”
The Fix: Look for ways strategies can compound each other. ClickUp’s 11x LTV lift from combining PLG and sales-led growth proves these approaches can be synergistic, not competitive.
3. Getting Stuck at Local Maximum and Stopping Innovation
The Mistake: Once companies find what works, they optimize that single approach to death instead of continuing to explore new opportunities. They become comfortable and stop pressure-testing for better distribution tactics.
The Fix: Always assume there are better strategies you haven’t discovered. Maintain the 70-20-10 resource allocation where 30% of resources go toward new opportunities, even when current channels are performing well.
4. Abandoning Compounding Channels Too Early
The Mistake: Companies give up on long-term compounding channels (community, SEO, viral features) because they don’t see immediate results, instead over-investing in diminishing return channels like paid ads because they’re more predictable.
The Fix: Understand which channels have infinite scaling potential versus those with natural limits. Invest in building compounding channels even when they take longer to show results, while using diminishing return channels for predictable short-term growth.
The Bottom Line: No Hacks, Just Fundamentals
There are no secret growth hacks for building a sustainable, ever-growing revenue machine. Success comes from:
- Understanding your positioning in the LTV/TAM matrix and choosing appropriate strategies
- Learning from the best-in-class regardless of industry
- Avoiding zero-sum thinking and finding ways to combine approaches
- Building a diversified growth portfolio with the right risk/reward balance
- Investing in compounding channels while managing diminishing return channels
- Maintaining hunger and constantly seeking better opportunities
- Using AI to 10x velocity across every step of your revenue machine
The competition is getting fiercer every day. ClickUp is now accelerating at $300,000,000+ ARR. How about you?
