SaaStr 816: PLG to Enterprise to SMB: Insights from Calendly's CEO
Join us as Jason Lemkin, CEO, and Founder of SaaStr, sits down with Tope Awotona, CEO, and founder of Calendly for an insightful AMA session. They discuss Calendly's journey, their success in the Product-Led Growth (PLG) domain, and how it balances self-serve with enterprise sales strategies. Tope shares candid lessons learned from growing Calendly, from managing customer acquisition costs to aligning product development with customer needs. The conversation also delves into how Calendly plans to integrate AI to enhance user productivity and manage meetings more efficiently. This episode is packed with valuable insights for founders, CEOs, and anyone interested in SaaS growth strategies.
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Hey everybody, SaaStr Annual will be back in May of 2026.
The world's largest SaaS + AI gathering for executives. Just this May we hosted: 10,000 attendees with 68% VP-level and above, 36% CEOs and founders and a growing 25% were AI-first professionals. This is the very best of the best S-tier attendees and decision makers that come to SaaStr each year.
But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait.
Lock in your spot today. Use my code JASON100 for exclusive savings. Get your tickets at podcast.saastrannual.com or use code JASON100 at checkout.
SaaStr Annual 2026. We'll see you there
SaaStr 721: How Revenue Leaders at Box, Calendly, and Lattice Scaled From $0 to $100M+ and Beyond
SaaStr 721: How Revenue Leaders at Box, Calendly, and Lattice Scaled From $0 to $100M+ and Beyond
Mark Roberge, SaaStr fan-favorite and Co-Founder and Managing Director of Stage 2 Capital brought together some of the top CROs in SaaS during the SaaStr Annual to share some of their greatest learnings and pivotal moments leading some of the Cloud 100 SaaS companies.
Dini Mehta, former CRO at Lattice, Kate Ahlering, CRO at Calendly, and Mark Wayland, CRO at Box, share their stories and offer advice to founders on:
How do you define and refine an ICP?
Can you start and stop a PLG motion?
What should you look for in an Enterprise rep vs. a Mid-Market rep?
How do you diagnose and solve churn?
How should you handle presenting challenges to your C-suite team when you've just joined the company?
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SaaStr hosts the largest SaaS community events on the planet.
Join us in 2024 at:
SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20
SaaStr Europa: June 5-6 in London. We'll be hosting the 5th SaaStr Europa in London for two days of content and networking. Join 3,000 SaaS and Cloud leaders. Podcast listeners can grab a discount on Europa tickets here: https://www.saastreuropa2024.com/buy-tickets?promo=fave200
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Calendly: Tope Awotona (2020)
After emigrating from Nigeria to the US to attend college, Tope Awotona worked as a door-to-door salesman and eventually set out to become a tech entrepreneur. He launched a series of e-commerce businesses that quickly fizzled when he realized he had no passion for them. But then he landed on an idea he was truly excited about: designing software that would minimize the hassle and headache of scheduling meetings. In 2013, he cashed in his 401k and went into debt to build Calendly, a scheduling service reportedly doing over $100 million in revenue.
This episode was produced by Rachel Faulkner-White, with music by Ramtin Arablouei
Edited by Neva Grant, with research help from Daryth Gayles.
You can follow HIBT on Twitter & Instagram, and email us at hibt@id.wondery.com.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Think like an outsider, w/Shellye Archambeau, Ellevest’s Sallie Krawcheck, and Calendly’s Tope Awotona
How do you evolve your greatest obstacle into your greatest superpower? Shellye Archambeau, Ellevest’s Sallie Krawcheck, and Calendly’s Tope Awotona discuss the hidden advantages of strategizing like an entrepreneurial outsider. Recorded live at the Masters of Scale Summit in San Francisco, they sit down with host Bob Safian to share lessons about questioning the status quo, maintaining confidence in the face of criticism, and orchestrating a cultural turnaround. Whether you’re a budding entrepreneur or firmly established in the C-suite, the outsider’s mindset has the power to inject counterintuitive creativity and dynamism into your leadership.
Read a transcript of this episode: https://mastersofscale.com/
Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)
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Annie Pearl is the Chief Product Officer at Calendly. Previously, she was Chief Product Officer at Glassdoor, as well as Director of Product Management at Box. She was named one of the most influential women in Bay Area business by the San Francisco Business Times. In today’s episode, Annie shares three paths into product management and advice on how to get your foot in the door. She also gives us an inside look at how Calendly’s product teams are structured, how they transitioned from solely PLG to adding a sales team and unlocking new growth levers, how they do planning, and much more.
Find the full transcript here: https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid
Where to find Annie Pearl:
• LinkedIn: https://www.linkedin.com/in/anniepearl/
• Email: Annie.Pearl@calendly.com
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• Twitter: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
Referenced:
• How to send a calendar invite with Calendly: https://calendly.com/blog/how-to-send-a-calendar-invite
• Google’s APM program: https://careers.google.com/programs/apm/
• The 15 Best Associate and Rotational Product Manager Programs: https://medium.com/agileinsider/product-management-digest-apm-3c2631683139
• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X/
• Confluence: https://www.atlassian.com/software/confluence
• Aha: https://www.aha.io/
• Airtable: https://www.airtable.com/
• Loom: https://www.loom.com/
• Jira: https://www.atlassian.com/software/jira
• Pendo: https://go.pendo.io/
• Tope Awotona on LinkedIn: https://www.linkedin.com/in/bawotona/
• The Skip podcast: https://www.skip.community/
• Skip Community on LinkedIn: https://www.linkedin.com/company/skip-community-for-cpos/
• Nikhyl Singhal on LinkedIn: https://www.linkedin.com/in/nikhyl/
• Good to Great: Why Some Companies Make the Leap and Others Don’t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996
• Hooked: How to Build Habit-Forming Products: https://www.amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/0241184835/
• 20VC podcast: https://www.thetwentyminutevc.com/
• Sing 2 on Netflix: https://www.netflix.com/title/81475311
• Miro: https://miro.com/
In this episode, we cover:
(00:00) Annie’s background
(03:50) How to send a Calendly invite without feeling awkward
(06:04) How to transition to product work from a non-technical career
(09:53) APM programs
(10:52) The characteristics of internal-transfer PMs
(13:26) How Calendly structures product teams
(14:57) Why Annie hired a Head of Design
(16:58) How Calendly structures product teams
(19:07) OKRs at Calendly
(21:02) Changes made at Calendly to improve execution and shipping
(22:45) The challenges with narrowing Calendly’s customer base and adding sales
(25:21) Where 70% of new Calendly users come from
(26:17) The transition from PLG to sales
(29:23) How to build a great relationship with your sales team
(31:52) Planning and prioritization at Calendly
(38:14) Strategy documents at Calendly
(39:39) Calendly’s product stack
(40:21) How Calendly got their first 1,000 users
(43:36) The surprising new growth levers at Calendly
(46:05) Fun traditions
(48:43) “Focus wisely” and other aspects of Calendly’s culture
(52:07) Learnings from Box and Glassdoor
(54:57) The Skip Community
(58:10) Lightning round
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
20Product: When to Hire a CPO, The Three Different Types of CPO, How To Know What You Need, How To Structure the Hiring Process, What Are the Must-Ask Questions, What Tests and Case Studies Should Be Used, How Should Their Compensation Package Be Structur
Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70-person product and design org.
Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe's first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter.
David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos.
Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay.
Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products.
Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack.
For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015.
Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe's Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012.
In Today's Episode on How to Hire a Product Manager, We Discuss:
1.) When to Hire Your First PM:
What are the core signs that the founder must delegate and hire their first PM?
What are the first things that are breaking when you do not have one but need one?
How does the timing of the first PM differ when comparing B2B vs B2C?
2.) What is the Right Profile:
What should founders look for in this first PM hire? What traits make the best?
What are the biggest red flags in the personalities and styles of potential candidates? Should they have experience in the product domain they are entering?
What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume?
3.) The Hiring Process: How To Hire a Product Manager
How do we structure and run the hiring process for this person?
What tests can we do to understand if they have the skill set we need for the role?
How do we structure a hiring panel to make this process more effective?
What are the biggest mistakes founders make in the hiring process for PMs?
20Product: Calendly CPO Annie Pearl on Why All PLG Companies Eventually Need to Embrace Enterprise, Why it is Easier to Scale into Enterprise than Visa Versa and the Calendly PLG Playbook; What Works and What Does Not?
Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10M users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70 person product and design org. Prior to Glassdoor, Annie led enterprise product teams at Box both before and after their 2015 IPO. If this was not enough, Annie is also on the Board of WorkRamp and Well Health.
In Today's Episode with Annie Pearl We Discuss:
1.) Entry into Product From Consulting:
How did Annie make her way into the world of product and come to lead product teams at Box and GlassDoor?
What are 1-2 of her biggest takeaways from her time at Box and GlassDoor? How did they impact her product mindset?
What does Annie know now that she wishes she had known when she started in product?
2.) PLG vs Enterprise: What, When, How:
Is it possible to do PLG and top-down enterprise strategy together from Day 1?
Why does every PLG company eventually have to adopt an enterprise strategy?
What are the single biggest challenges companies face when moving to enterprise?
How do founders know when is the right time to make this transition?
How do founders need to restructure their org to make the transition to enterprise?
3.) Building the Product Bench: Hiring:
When is the right time to hire your first product leader? What are the core signals?
What are the core character traits needed for a first product leader?
How do we specifically structure the interview to test for them?
Who do we bring into the interview process from other parts of the org?
Do we do case studies with candidates? If so, how long do they have with the data? What is the difference between good vs great with case studies?
4.) Product Strategy, Reviews and Alignment:
How does Annie assess how often product strategy should be reviewed? When should it change?
How does Annie approach post-mortems? What is the right way to structure them?
How does Annie create alignment between sales and product? Why is this so important?
What is the single biggest product mistake Annie has made? What did she learn?
CRO Calendly, Kate Ahlering: Embracing Leadership - On and Off the Basketball Court
Kate Ahlering might be the perfect guest for this podcast. She eventually worked her way up to Chief Sales Officer of Glassdoor, but when she joined in 2013, she helped define the company’s leadership framework as GRIT: Growth, Results, Integrity, and Team. Glassdoor has continued using those values since her departure in 2020, and now as the CRO of Calendly, she is applying a similar framework to another fast-growing enterprise.
In this episode, Kate and Joubin discuss her first leadership experience, captaining her college basketball team before ever playing a game; the wild ride of working at Glassdoor when it was doubling every year; the perspective and confidence that comes from working experience; brokering consensus when deciding a company’s values; the increasingly complex use cases for Calendly; and a ridiculous Twitter feud over “Calendly etiquette.”
In this episode, we cover:
Kate and Joubin’s past interactions, including a disagreement over San Diego cuisine (03:02)
How being raised by two salespeople and playing basketball at the University of Virginia shaped Kate’s worldview (06:01)
Working at Glassdoor “never felt easy,” but she later realized it was a once-in-a-lifetime experience (14:47)
Her big legacy at Glassdoor, defining its values as GRIT: Growth, Results, Integrity, and Team (20:38)
Building trust with a team in a rapidly-changing environment, and working alongside Indeed — a former competitor now owned by Glassdoor’s parent company (26:16)
Calendly’s interview process and the dangers of offering a thorough plan before you’re inside the company (32:08)
The surprising depths of Calendly’s complexity in enterprise, and why founder Tope Awotona (accidentally) made the business model freemium (36:15)
Kate could have gone almost anywhere after Glassdoor — why she chose Calendly, and what motivated her to achieve? (42:36)
When she’s going to bed every night, what does Kate wish she was spending more time on? (48:14)
Links:
Connect with KateLinkedIn
The profile of Kate as a UVA basketball captain
Connect with JoubinTwitter
LinkedIn
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm
SaaStr 524: From New Relic to Salesforce to Calendly: What's Changed in Product-led Growth with Calendly CMO Patrick Moran
The world of product-led growth is a highly dynamic space. Join this session with Calendly CMO Patrick Moran and Head of Marketing Growth & Demand Gen Garrett Scott to learn more about these changes and how they are reflected in Calendly's evolution as a SaaS company.
Full video: https://youtu.be/ey9aiYOupSg
Blog post: https://www.saastr.com/whats-changed-in-product-led-growth-with-calendly-cmo-patrick-moran/
Want to join the SaaStr community? We're the 🌎largest community for B2B software.
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SaaStr 494: Demystifying the Unicorn Buzz with the CEOs of Calendly, Algolia, and Contentful
Reaching unicorn status is goal #1 for many startups. In this podcast, Tope Awotona, CEO at Calendly, Bernadette Nixon, CEO at Algolia, Steve Sloan, CEO at Contentful and by Casey Renner, Partner at OpenView discuss how high-growth companies can strive for profitability while growing responsibly to reach unicorn status.
Blog post and video: https://www.saastr.com/demystifying-the-unicorn-buzz-with-the-ceos-of-calendly-algolia-and-contentful/
Sponsors:
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Calendly: Tope Awotona
After emigrating from Nigeria to the US to attend college, Tope Awotona worked as a door-to-door salesman and eventually set out to become a tech entrepreneur. He launched a series of e-commerce businesses that quickly fizzled when he realized he had no passion for them. But then he landed on an idea he was truly excited about: designing software that would minimize the hassle and headache of scheduling meetings. In 2013, he cashed in his 401k and went into debt to build Calendly, a scheduling service expected to make about $60 million this year.
Pre-order the How I Built This book at:
https://smarturl.it/HowIBuiltThis See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
SaaS Product Validation: 3 Failed Startups to Calendly
Three failed startups. A dating site, projectors, and grills. Tope Awotona spent years chasing money instead of solving real problems. Then he wasted an entire day scheduling a meeting and found what was missing. That problem became Calendly - now serving 4 million users at $30M ARR. In this episode, Tope shares the SaaS product validation lesson that changed everything.
Tope's approach to SaaS product validation was unconventional: he did not interview a single potential customer. Instead, he studied existing scheduling tools with paying customers as proof of demand, used those products himself to find gaps, and read user forums to understand what people loved and hated - a form of idea validation through market observation.
Calendly launched free by accident (they ran out of money before building billing) and became freemium by design. The viral nature of scheduling meant every invite exposed new users to the product, turning product-market fit and SaaS product validation into organic growth that reached 4 million users without traditional marketing.
🔑 Key Lessons
🎯 SaaS product validation requires passion, not profit motives: Tope's first three startups failed because he was chasing money. Calendly worked because scheduling pain was his own frustration from seven years in sales.
💡 Validate by observing behavior, not conducting interviews: Tope did not talk to a single customer. He validated demand by seeing existing tools with paying customers - a practical approach to startup validation.
🛠️ Optimize for the recipient's experience in SaaS product validation: Calendly won by reducing friction for invitees rather than only serving account holders. Fewer clicks and automatic timezone detection made scheduling effortless.
🚀 Freemium plus virality equals organic growth: Calendly launched free by accident and reached 4M users through viral sharing. Every meeting invite exposed new users to the product.
💰 Go all-in when SaaS product validation confirms product-market fit: After three part-time failures, Tope emptied his bank account, flew to Ukraine to hire engineers, and committed full-time to Calendly.
Chapters
Introduction
What Calendly does and who uses it
Growing up in Nigeria and moving to the US
Three failed startups before Calendly
Why the projector and grill businesses failed
Taking a sabbatical from entrepreneurship
How the idea for Calendly came about
Spending months on SaaS product validation
Idea validation without customer interviews
Emptying his bank account to go all-in
Hiring engineers in Ukraine
Differentiating on invitee experience
How Calendly got its first 1,000 users
The accidental freemium model
When Calendly started charging (and the mistake)
Reaching $30M ARR and 4 million users
The emotional rollercoaster of scaling
Hiring too fast vs hiring too slow
Lightning round
Resources
Full show notes: https://saasclub.io/213
Join 5,000+ SaaS founders: https://saasclub.io/email
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