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A key insight from the podcast episode revolves around the importance of having a clear product strategy that focuses on a specific target market. The strategy should define where to play and how to win in that market. This approach helps prioritize work by identifying the markets, segments, and personas to target, ensuring that resources are allocated effectively.
The discussion highlighted the significance of transparent resource allocation and horizon planning in product development. By dividing resources based on different horizons aligned with the company's vision, teams can efficiently prioritize work. For example, allocating resources more to Horizon 2, which aligns with short to medium-term goals, can signify progress towards the company's overall strategy.
The podcast episode emphasized the challenge of balancing product requests from users, like requesting a Venmo integration, with the company's strategic direction. Despite user demand, features that do not align with the target market or long-term vision are deprioritized. This showcases the importance of staying focused on the defined strategy to guide product decisions and prioritize initiatives.
The conversation underscored the notion of strategy as an integrated set of choices for success in the market. By defining a winning aspiration, target markets, segments, and personas, companies can effectively plan their product roadmap. This integrated planning approach ensures alignment across teams and resources, streamlining decision-making and driving progress towards strategic objectives.
Calendly focuses on a structured product development lifecycle involving phases like discovery, solutioning, build, and launch. Each phase involves committing to specific tasks within their control, allowing for better planning and estimation.
Annie mentions her involvement in the Skip Community, a group of CPOs aimed at sharing advice and support. Calendly's culture emphasizes focus wisely, instilling the importance of focusing on target users and markets. This focus has been integrated into various processes, templates, and documentation to drive effective product development.
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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.
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Listen to the best highlights from the podcasts you love and dive into the full episode