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Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)
42 segments available
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. — Brought to you by Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny | Coda—Meet the evolution of docs: https://coda.io/lenny | Vanta—Automate compliance. Simplify security: https://vanta.com/lenny 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.
Segments Timeline
Annie Pearl's Journey to Product Management
Annie Pearl shares her unique path to becoming a Chief Product Officer, highlighting her transition from law to product management. She discusses her experiences at various companies, including Glassdoor and Box, and emphasizes the importance of product strategy in achieving success in the marketplace.
"strategy is really just an integrated set of choices that outline how you're going to win in whatever Marketplace you choose right and so a good product strategy is going to answer questions like what..."
The Power of Calendly: Scheduling Without Awkwardness
Annie Pearl provides actionable tips on how to use Calendly effectively without making the recipient feel uncomfortable. She suggests opening the conversation by inviting the other person to share their availability first, and then offering the Calendly link as an option, making the scheduling process smoother and less awkward.
"short word from our wonderful sponsors today's episode is brought to you by Nero an online collaborative whiteboard that's designed specifically for teams like yours I have a quick request head on ove..."
Paths to Product Management
Annie discusses various paths to entering product management, especially for those coming from non-technical backgrounds. She outlines formal options like Associate Product Manager (APM) programs and informal methods such as shadowing a product manager or applying for junior roles within a company.
"ready-made templates you can go from Discovery and research to product roadmaps to customer Journey flows to final mocks all the in Miro head on over to miro.com to leave your suggestions that's miro...."
The Importance of Internal Transfers
Annie emphasizes the value of internal transfers for transitioning into product management roles. She shares insights on how expressing interest and taking on product-related tasks can help individuals move into product management from other functions within their organizations.
"startup credit of one thousand dollars coda.io Lenny Annie welcome to the podcast thanks for having me Lenny super excited to be here I've been a big fan of yours from afar we've crossed paths a littl..."
Characteristics of Successful Product Managers
Annie outlines key characteristics that successful product managers often possess, such as curiosity, passion for the product, and a proactive approach to solving customer problems. She highlights the importance of demonstrating eagerness and interest in product management to increase one's chances of success.
"before you offer up your channel link I think is you know a little bit of a subtle way to let them take the lead if they want the second piece I would recommend too is once you kind of open that door ..."
Challenges of Establishing APM Programs
Annie discusses the challenges companies face in establishing Associate Product Manager (APM) programs. She explains that creating a successful program requires significant investment and resources, which can be a barrier for many organizations, especially smaller ones.
"people for when they ask you how to transition into a product role I got you know what I'll call Lucky which is I kind of stumbled into product management after law school joined the founding team of ..."
Finding APM Opportunities
Annie shares practical advice on how to find APM opportunities, including searching on platforms like Glassdoor for open roles. She encourages aspiring product managers to explore both large tech companies and smaller startups for potential APM positions.
"out opportunities to kind of Shadow or partner closely with with a product manager and maybe even offer to take on some work so some of the kind of best PMS that I've brought over to product from kind..."
Navigating APM Programs
Annie Pearl shares valuable insights on how to find Associate Product Manager (APM) roles, emphasizing the importance of internal transfers and the characteristics that make candidates successful. She discusses the rarity of APM programs and the effort required to establish them effectively within a company, highlighting the need for clarity in roles and training to ensure success.
"I think you'll find a whole host of open roles that you might be able to apply to that is a cool tip I haven't heard of that go to Glassdoor and search for APM so you search for companies that have an..."
The Challenge of APM Programs
Annie discusses the challenges companies face in establishing APM programs, including the need for significant investment and a structured environment to support the growth of associate product managers. She reflects on her experiences at previous companies and the complexities involved in creating a successful program.
"the same thing we found at Airbnb there's a PM that was so excited to like make the APN program and just just never really happens just take so much work and to your point you have to set up for Succe..."
Breaking into Product Management
Annie highlights the difficulties of entering product management due to the limited number of roles compared to other functions. She provides actionable advice for aspiring product managers on how to navigate this competitive landscape and successfully transition into the field.
"actually want to that's right okay so I want to transition a little bit to talking about calendly there's kind of two areas I want to go one is just how do you build product accountantly what have you..."
Calendly's Product Development Insights
Shifting focus to Calendly, Annie Pearl discusses the structure of product teams and the lessons learned about product development and team building. She shares insights on the growth of the product team and how they are organized to enhance collaboration and efficiency.
"600 now and then the product team worked out there were about 15 product managers and designers when I joined again about two years ago and I think were around 60 uh this year wow so 60 product manage..."
Integrating Design and Product
Annie explains the rationale behind integrating design with product management at Calendly. She shares her experience leading both functions and emphasizes the importance of a cohesive user experience, which is achieved through this integrated approach.
"orgs is design reporting up to a product leader versus not what's the rationale there and then has County tried a different approach yeah so when I was at Glassdoor in the CPO role I had the opportuni..."
Building a Design Team
Annie discusses her decision to hire a Head of Design at Calendly, highlighting the importance of leadership in the design function. She reflects on the previous lack of design leadership and how this change has positively impacted the product's user experience.
"customers so it sounds like before you joined it wasn't like that and if that's true was there like something that improved with that shift so the structure was there that way at the time we didn't ha..."
Structuring Product Teams
Annie provides an overview of how Calendly structures its product teams, focusing on core user experiences, enterprise needs, and platform integration. She explains how these teams are organized around specific personas and outcomes to enhance product development.
"so we have you know core team who's really responsible for the core you know end-to-end user experience and you know in many ways they're both building you know doing feature development and then they..."
Understanding OKRs at Calendly
Annie discusses the implementation of OKRs (Objectives and Key Results) at Calendly, detailing how they are used at both company and department levels. She shares insights on the evolution of OKRs within the organization and their role in aligning teams towards common goals.
"that we you know provide our product into and so that's everything from you know Partnerships and Integrations to our apis interesting so it's kind of like problem focused slash Persona Focus like who..."
Transforming OKR Practices
Annie reflects on the transformation of OKR practices at Calendly, emphasizing the importance of integrating OKRs across the organization. She discusses the impact of this integration on team collaboration and the overall success of the company's objectives.
"muscle well built out right we we didn't really have a clear product strategy at the time or clear okrs guiding the work and so there was a lot of great work happening but it really it was unclear how..."
Enhancing Execution and Shipping
Annie shares key changes made at Calendly to improve execution and shipping processes. She discusses the challenges faced with a broad user base and how refining the product strategy has enabled better prioritization and delivery of value to target users.
"do as a business so what I'm hearing is one of the biggest changes in learnings was to connect our carers across from the top to the bottom right absolutely absolutely is there anything else that has ..."
Defining Target Markets
Annie concludes by discussing the importance of defining target markets and personas for product development. She highlights how this clarity has helped the team prioritize effectively and deliver better solutions for their core users.
"users so it sounds like the biggest unlock and one of the biggest unlocks for making the team more efficient move faster make decisions quicker is narrowing in on exactly who you're going to be sellin..."
The Viral Growth Loop of Calendly
Annie reveals that 70% of new signups for Calendly come from a viral loop, where solo users invite team members, leading to broader organizational adoption. This organic growth model highlights the effectiveness of Calendly's product in fostering user engagement and expanding its reach within companies. Understanding this growth mechanism is essential for optimizing sales strategies and targeting potential leads.
"then the product itself of course has to change so I guess let's just say the example of plg and SLG or the direct selling motion is you know tying to your question around what are the things that nee..."
Hiring for Sales Success
Annie shares insights on hiring the right sales team as Calendly transitions to a sales-led growth model. She emphasizes the importance of recruiting sales reps with experience in inbound sales, as the initial focus is on leads that have shown interest in the product. This approach contrasts with the need for outbound sales profiles in later stages, highlighting the evolving nature of the sales strategy.
"that everybody wishes they could it's pretty incredible I will say no man okay so going back to the question when did Colony hire their first salesperson like any learnings about just how to start dow..."
Understanding the Target Buyer
Annie discusses the importance of understanding the target buyer when transitioning to a sales-led model. She explains that early sales efforts should focus on department heads rather than senior IT personnel, which requires a different sales approach. This understanding is crucial for aligning the sales team's skills with the needs of the target market, ensuring effective customer acquisition.
"reps just one quick question on that actually because that's really interesting I don't know how involved during hiring these folks but is it like look at their background and they've worked at a comp..."
Building Relationships with Sales Teams
Annie emphasizes the value of building strong relationships between product and sales teams. She advocates for viewing the sales team as a vital asset that can provide insights into customer needs, which is essential for product development. Her experience at Box illustrates how close collaboration with sales can lead to better product decisions and ultimately enhance customer satisfaction.
"certainly several years away and so making sure that the the profile of the folks you're bringing on early match that Target buyer in addition to match the motion around how you're going to be acquiri..."
Prioritizing Product Development
Annie outlines her approach to prioritizing product work amidst various demands from sales and stakeholders. She stresses the importance of having a clear product strategy that guides decision-making. By utilizing frameworks like 'Playing to Win,' she ensures that the product team focuses on delivering value to a defined target audience, rather than trying to cater to everyone.
"helping you streamline your security compliance to accelerate growth if your business stores any data in the cloud then you've likely been asked or you're going to be asked about your sock 2 complianc..."
Crafting a Winning Product Strategy
Annie Pearl discusses the importance of having a clear product strategy as a foundation for prioritization in product management. She introduces a framework from the book 'Playing to Win,' emphasizing the need to define winning aspirations, target markets, and how to achieve success within those markets. This segment highlights how a well-defined strategy helps product teams focus on delivering value to specific personas rather than trying to cater to everyone.
"approaches for just deciding what to actually build of all the things you're hearing the core challenge of being a product manager right just so that that like I feel like the core job of PM is just t..."
Prioritizing Features Based on Strategy
Annie shares insights on how Calendly prioritizes features based on their product strategy. She provides an example of how the company has chosen to de-prioritize a Venmo integration due to its misalignment with their target market, which focuses on sales teams and customer success teams. This segment illustrates the importance of aligning product decisions with strategic goals.
"don't know how much you could share here but is there a feature that is like people keep asking for it and it hasn't been built because of the strategy the long-term Vision something that's like nope ..."
Planning and Roadmapping at Calendly
In this segment, Annie explains how Calendly approaches planning and roadmapping. She discusses the company's OKRs (Objectives and Key Results) and how they break down annual goals into quarterly milestones. Annie emphasizes the importance of having a clear strategy to guide the planning process and how they commit to phases of product development, from discovery to launch.
"example I want to get back to the growth stuff but before I do that we're kind of on this topic of planning and who cares and organization I'd love to know just how you do planning accountantly like h..."
The Phases of Product Development
Annie outlines the phases of Calendly's product development lifecycle, which include Discovery, Solutioning, Build, and Launch. She explains how each phase is structured and the importance of committing to work that is within their control. This segment provides a clear framework for understanding how Calendly approaches product development and the iterative nature of their process.
"a model of talking about dates and promising and committing to dates that are within our control and so if you think about kind of the product development life cycle you know we can commit to a discov..."
Strategic Documentation at Calendly
Annie discusses the strategic documentation process at Calendly, including the high-level three-year strategy and how it is communicated within the company. She explains the use of OKRs at the product team level and how they utilize tools like Confluence for documentation. This segment sheds light on the importance of transparency and alignment in strategic planning.
"kind of designed the product development life cycle around that framework so Discovery for example is that like a roadmap item for a quarter and that's like what you've committed to and if that goes w..."
How Calendly Gained Its First Users
Annie shares the story of how Calendly acquired its first users, highlighting the role of customer success agents from a partner firm in the education sector. She explains how these initial users helped spread the word about Calendly, leading to organic growth. This segment illustrates the unconventional yet effective strategies that contributed to Calendly's early success.
"so maybe on that topic what are what else is in the stack of calendly product Team Tools we talked about roadmap planning some combination of starts with docs there's mural boards involved uh usually ..."
The Surprising Growth of Team Accounts
Annie reveals that while Calendly is often seen as a tool for individual users, the growth of team accounts is actually outpacing solo user growth. She discusses how supporting teams and departments is where the future growth potential lies for Calendly. This segment highlights the evolving understanding of Calendly's user base and the strategic focus on collaborative scheduling.
"organically from there so that was one piece I think the other piece that's really important is that he started off by you know just having a free tier the entire product was free some of this came fr..."
The Reality of Viral Growth
In this segment, Annie addresses the misconception that viral growth can sustain indefinitely. She explains the need for active growth strategies as user acquisition slows down, especially as the company scales and reaches a larger audience.
"organization it's interesting when you hear the story of accounting that just has so many good things happening like basically for free it's just gross so well I think people don't realize you eventua..."
Customer-Driven Product Development
Annie highlights how Calendly's growth strategy is shaped by customer feedback and usage patterns. She explains that the company was pulled into supporting team functionalities based on how customers were using the product, showcasing a responsive approach to product development.
"the the beauty of calendly is that while we certainly have built features of functionality to support teams and and departments we got pulled there right it wasn't one of those things where we sort of..."
Unique Team Traditions at Calendly
Annie shares some fun and unique traditions within Calendly's product team, including the 'Oppa' meeting for opportunity and problem assessment. This segment illustrates how the team collaborates and debates ideas to enhance product development.
"what are some fun or unique traditions and cultural kind of components of the calendly product team the ones I thought we could talk about one we have a meeting called oppa which stands for opportunit..."
Competitive Wargaming for Product Insights
Annie explains the concept of competitive wargaming, where team members analyze competitors and present their findings. This engaging exercise fosters a collaborative environment and helps the team stay informed about market trends.
"meeting where PMs present their plans to all the other PMS he's like it was like it's like you're like like in a shark tank where everyone's coming to destroy you they just point out all the problems ..."
Focusing Wisely: A Core Value
Annie discusses the core value of 'focusing wisely' at Calendly, emphasizing the importance of targeting specific user needs. She explains how this principle is embedded in the company's culture and product development processes.
"gaming that is cool it's really impressive how you do these exercises and they're seemingly positive and friendly and constructive it sounds like it's kind of a there's a pretty unique culture account..."
Lessons from Previous Roles
Reflecting on her experiences at Box and Glassdoor, Annie shares key lessons learned about understanding customer needs and building scalable solutions. She highlights how these insights have shaped her approach at Calendly.
"starts with you know some of the broader cultural paradigms that exist at the company and then we've now embedded that into the way we think about how we build product is there anything else you do to..."
Bridging Consumer and Enterprise Insights
Annie explains how her diverse experiences in consumer and enterprise product management have influenced her work at Calendly. She discusses the blend of strategies from both sectors that contribute to the company's growth.
"and specific teams of users within departments before Gallery you were at box before that you're a glass door I'm gonna ask two different questions you can pick which direction you want to go what wou..."
Learning to Ask the Right Questions
Annie Pearl shares her biggest learning from her time at Box, emphasizing the importance of asking the right questions to understand customer needs. She discusses how building solutions that cater to a broader audience is crucial for maintaining a positive end-user experience, rather than just fulfilling individual customer requests.
"business and I'd say my biggest learning during that time was around how to ask the right questions to really understand the why behind what a customer was asking for and then figuring out how to buil..."
Bridging Consumer and B2B Insights
Transitioning from Box to Glassdoor, Annie explains how she learned to manage both consumer and B2B aspects of a marketplace. She highlights the significance of consumer engagement and the strategies she employed to optimize user experience and drive traffic, which she later applied at Calendly.
"together to calendly but a cool set of experiences I'm trying to imagine using all three in the same day sending accountantly storing your files in a box looking at reviews and recruiting and recruiti..."
The Skip Community: A Support Network for CPOs
Annie discusses her involvement in the Skip Community, a support group for Chief Product Officers facing similar challenges in late-stage growth companies. She explains how the community fosters collaboration, advice sharing, and professional growth, enhancing the effectiveness of product leaders.
"grow one of them is you know we're actually partnering with some companies right now to experiment with how can we help them as they're looking to make their first head of product higher or their firs..."
Joining the Skip Community
Annie provides insights on how to join the Skip Community, emphasizing its focus on supporting heads of product and CPOs in navigating their roles. She encourages interested individuals to connect with current members and follow the community on LinkedIn for updates and opportunities.
"what is a very hard role I love this I imagine when people look at a CPO they imagine they just like know everything already they have a bunch of friends in the same role but I think in reality it's l..."
Lightning Round: Quickfire Questions
In a rapid-fire segment, Annie answers questions about her favorite books, podcasts, and movies, sharing insights into her personal preferences and professional recommendations. She also discusses her best tips for using Calendly effectively, showcasing the platform's new features.
"notes as well well with that we've reached our very exciting lightning round I've got six questions for you are you ready let's do it what are two or three books that you recommend most to other peopl..."