When you think about Product-Led Growth (PLG) success stories, few companies exemplify the model better than Calendly. Founded in 2013 by Tope Awotona, Calendly has grown from a simple scheduling tool to a scheduling powerhouse that’s touched “double digits” of the world’s billion knowledge workers – meaning over 100 million people have used the platform at some point.
At SaaStr Annual + AI Summit, Awotona shared the hard-won lessons from building one of the most successful PLG companies of the last decade. What makes his insights particularly valuable is his transparency about the mistakes Calendly made along the way – and how they course-corrected.
Today, Calendly maintains a fascinating 90/10 revenue split between self-serve and sales-led motions, with customers ranging from individual contributors to million-dollar enterprise accounts. But getting that balance right took years of experimentation, data analysis, and some painful lessons about when PLG and enterprise motions can cannibalize each other.
Top 5 Key Learnings from Calendly’s Journey
1. The Free Plan Is Your Marketing Engine – Protect It at All Costs
Perhaps the most counterintuitive insight from Awotona: Calendly spends “almost zero dollars on marketing campaigns.” Their growth is entirely driven by user activity on the platform. Free users aren’t just prospects – they’re active marketing assets with measurable LTV.
“We’re happy for people to use the product for free,” Awotona explained. “Even free users have an LTV associated with them because we spend almost zero dollars on marketing campaigns.”
The pressure to tighten free plans is constant. Sales teams consistently identify the free version as their #1 competitor, not any external product. But since putting up their first paywall in 2014, Calendly has never removed features from the free plan – they’ve only made it more generous.
The Takeaway: If your free plan drives viral growth, resist the short-term temptation to squeeze it. Instead, add more value to paid tiers rather than removing value from free ones.
2. Viral Loops Get Harder at Scale – But Scale Compensates
Calendly closely tracks two critical metrics: meetings-to-signups conversion rates and signups-to-activation rates (defined as five people scheduling with a new user). As expected, these conversion rates decline at scale – the viral coefficient naturally decreases as you reach market saturation.
But here’s the key insight: “The good thing is the top line – the denominator – is getting bigger. That compensates a little bit for that degradation in conversion rate.”
The Takeaway: Don’t panic when viral coefficients decline at scale. Focus on optimizing the absolute numbers while understanding that percentage-based metrics will naturally compress as you approach market saturation.
3. Hybrid PLG + Enterprise Is Incredibly Hard to Get Right
This might be Awotona’s most valuable insight for SaaS leaders. Calendly made both classic mistakes in balancing PLG and enterprise motions:
Mistake #1: Under-investing in enterprise and leaving seven-figure deals on the table Mistake #2: Over-investing in enterprise and having the sales team cannibalize PLG revenue
“What we found was the growth in our customer acquisition cost outpaced the incremental revenue growth. The enterprise business was really cannibalizing the PLG business,” Awotona shared. By relaxing qualification rules to feed the sales team, they were simply converting self-serve prospects into sales-assisted deals – same revenue, higher cost, longer sales cycles.
The Takeaway: Be “incredibly analytical” with holdout groups and rigorous testing. The superficial metrics might look good while you’re actually damaging your more efficient channel.
4. External-Facing Roles Are the Wedge Into Enterprise
Calendly’s ideal customer profile focuses on external-facing roles: sales, customer success, recruiting. This represents about 25% of headcount in most organizations globally. But here’s the strategic insight: these users become the wedge for enterprise expansion.
Their largest customer – a financial services company doing $1M+ in annual revenue – started with “a few people in the company using it. They loved it and then decided to expand.” The expansion took 6-8 months from a sub-$20K footprint to seven figures.
The Takeaway: Identify the roles that get the most value from your product and use them as your enterprise wedge. Let the product prove itself with end users before enterprise sales gets involved.
5. Product Development Resource Allocation Must Match Business Model Evolution
With a 90/10 revenue split (PLG/Enterprise), how do you allocate product and engineering resources? Awotona’s answer has evolved significantly:
- Initially: 90/10 allocation matching revenue
- 2020 Growth-at-all-costs era: Asymmetric allocation heavily favoring enterprise
- Today: “The pendulum has swung back” based on product maturity and diminishing returns analysis
“We look at the maturity of the product for different cohorts and analyze where we’re hitting diminishing returns,” he explained.
The Takeaway: Resource allocation should be dynamic, based on product maturity and ROI analysis, not just revenue percentages. Sometimes your PLG motion needs more investment despite generating most revenue efficiently.
Tope’s Top 4 Mistakes (In His Own Words)
1. Over-Staffing Enterprise Sales During Growth-at-All-Costs Era
“We expanded that sales team greatly in 2020. Revenue grew, accounts over $100K grew, but customer acquisition cost outpaced incremental revenue growth. The enterprise business was cannibalizing the PLG business.”
2. Under-Analyzing the Hybrid Motion
“I thought we were very analytical ourselves, but there’s a lot more analysis we could have done, a lot more testing with holdout groups. When we ended up doing them, it was pretty eye-popping what we saw.”
3. Relaxing Sales Qualification Rules Too Much
“We relaxed the qualification rules for letting people talk to a salesperson. What we would see is that revenue would convert, but if we just let them self-serve, a lot of them would have converted anyway – same revenue, but you add time and friction to the deal.”
4. Not Being Strategic Enough About Product Allocation
“We’ve tried organizing teams by PLG vs Enterprise, by customer size, by capabilities. We’ve tried a number of different approaches. The most permanent design we’ve had is organizing by capabilities and having them own problems from individuals through enterprise.”
The common thread in all these mistakes? Not being analytical enough. Awotona’s biggest recommendation for founders building hybrid PLG-Enterprise motions: “Be incredibly analytical, do a lot of testing, use holdout groups.”
What looks like success on the surface might be masking fundamental problems with your go-to-market efficiency. Sometimes the “best” sales reps are actually the worst when you analyze cohort retention. Sometimes growing enterprise revenue is actually just expensive PLG revenue in disguise.
The companies that crack the hybrid code – like Calendly eventually did – are the ones willing to dig deep into the data and make hard decisions based on what they find, not what they hope to see.
