Calendly

Lenny's Podcast · Feb 26

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

About 70% of signups come through a viral loop, and product-led growth was 99% of ARR two years ago. Sales-led growth is now about 20% and the fastest growing segment, while the teams business grows much faster than solo. It narrowed to sales, recruiting and customer success personas, and the product org grew from about 15 to about 60 people.

Tips

• Narrow your product to a few target personas and say no▶ 23:17Narrowing to core ICPs was one of the most impactful changes Annie made early in her tenure for prioritization and execution speed.
• Write a product strategy that answers where you will play and how you will winCalendly's aspiration is to be the best place to schedule, prepare for and follow up on external meetings.
• Allocate team resources across strategy horizons and shift the split yearly▶ 34:19Horizon 1 investment went from about 70% to about 30% across three years as Horizon 2 grew to 60%.
• Commit to dates only for the phase you control▶ 36:45Calendly has gotten much better at making commitments on work right in front of it rather than on projects six months out.
• Hire early sales reps to match your inbound PLG motion and buyer▶ 26:35Sales-led growth went from roughly 1% of ARR to about 20% in two years and is now the fastest growing segment.
• Use product usage data to find team leads to sell into▶ 24:4070% of signups come through the viral loop of recipients seeing Calendly links.
• Expect viral growth to taper and follow where customers pull you▶ 44:52Calendly's teams business is growing much faster than its solo user business.
• Connect OKRs from the company level down to every department▶ 20:18Company-level integration was described as a really incredible transformation in how the company executes.
• Keep your leaders out of PM debate meetings to get honest feedback▶ 46:26PMs treat it as a meeting they need, and report getting a lot of value from it.
• Run quarterly competitor ownership and a wargaming day▶ 47:47
• Embed your focus into templates for docs, PRDs and reviews▶ 50:36Annie credits this culture for her success creating clarity on target personas.
• Put product and design under one leader at scale▶ 15:49
• Start PLG with a free product and a contractor team that doubles as first users▶ 41:30This path led to the first thousand users, then ten thousand and millions.
• Reduce scheduling friction by letting recipients share availability first▶ 5:00
• Ask candidates about their biggest product flop▶ 59:12

Lenny's Podcast · Sep 14

Picking sharp problems, increasing virality, and unique product frameworks | Oji Udezue (Typeform)

Onboarding asked only for a calendar connection and default hours. Activation was a first meeting, then five meetings in a week. Its ICP is sales, marketing and recruiting people who schedule with outsiders. It beat Acuity by being simple and respectful of the scheduler's time. Green dots add network effects.

Tips

• Build a great product on a sharp problem before adding viral tactics▶ 52:40Slack had no synthetic virality and spread by word of mouth at lunch; Calendly's virality worked where weaker schedulers like Acuity did not.
• Split onboarding into a mandatory setup of three screens or fewer and optional help▶ 40:50At Calendly the mandatory setup was connecting a calendar and setting defaults like 9 to 5, which set up later success. He says wizards have had limited benefit.
• Define three increasing activation thresholds and track drop-off between each▶ 44:20Calendly: first meeting created, then five in a week. Typeform: published a form, got responses, viewed insights. Twitter: following or being followed.
• Auto-schedule customer conversations on team calendars every week▶ 32:30Done at Calendly and Typeform; a popup linking to a Calendly booking page was used in the community.
• Process the customer signals you already receive through a triage workflow▶ 40:10He built a rig of workflows and Slack with individuals triaging at Calendly.
• Pick an ICP that cares most about the workflow, not the most obvious user▶ 15:03Calendly's ICP was salespeople, marketers and recruiters scheduling with outsiders; Typeform's is marketers; 30% of Twitter's customer base was media organizations like the NFL, NBA and HBO.

Lenny's Podcast · Aug 13

The ultimate guide to Martech | Austin Hay (Reforge, Ramp, Runway)

Hay calls it expensive, poor at syncing multiple calendars across business, consulting and personal use, with a 2016-era interface and a hard-to-remember link.

Lenny's Podcast · Apr 2

The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab)

Cited with Figma as a product with built-in virality where product-led acquisition pays off.

Lenny's Podcast · Mar 2

Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb)

A Ukrainian dev team built its first product, and it drove early growth because the team used it at their firm and it spread through Ukraine. That team is still part of its engineering.

Tips

• Get a technical co-founder rather than hiring contractors▶ 35:18YC rarely accepts teams that can't build their first prototype themselves; Gustaf recalls no success where a contracting team built the whole product.