calendly

Brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams

—

Oji Udezue is Chief Product Officer at Typeform and has held leadership roles at Twitter (Head of Product for Creation and Conversation), Calendly (CPO), and Atlassian (Head of Product for communication tools). He is well-known for bringing a product-led-growth (PLG) mindset to the companies he joins. Additionally, Oji mentors startups, is a Managing Partner at the Kernel Fund, and writes online about product management. In this episode, we discuss:

• Oji’s “Where to Fish to Land a Unicorn” and “Zone of Benefit” frameworks

• Why you need to find the “sharpest” problem

• How to operationalize continuous customer discovery

• Tips on optimizing onboarding flows

• Freemium vs. gated offerings in PLG

• Tactical strategies for making your product more viral

• The concept of “forest time” and how it can provide clarity in your work

—

Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.

—

Where to find Oji Udezue:

• Twitter/X: https://twitter.com/ojiudezue

• LinkedIn: https://www.linkedin.com/in/ojiudezue/

• Substack: https://substack.com/@ojiudezue

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter/X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Oji’s background

(03:38) Oji’s “Where to Fish to Land a Unicorn” framework

(05:26) Workflow quadrants

(09:30) How product people can push frequency 

(12:28) Oji’s “Zone of Benefit” framework

(14:49) How to find your ICPs

(15:33) ICPs at Twitter

(20:20) Oji’s philosophy on frameworks

(22:31) Oji’s upcoming book

(24:34) An explanation of “sharp problems”

(28:31) Signs your problem is “sharp enough”

(31:17) Discovery vs. continuous conversations

(35:08) Customer listening

(38:31) Onboarding fundamentals

(43:49) Activated user milestones

(45:47) The power of network effects

(50:15) An explanation of virality and how to increase it

(56:32) How to use “forest time” to zoom out and see problems in a new way

(1:00:53) Lessons from Oji’s time at Bridgewater Associates

(1:05:07) Why R&D teams need a larger system beyond Agile and design

(1:06:57) Lightning round

—

Referenced:

• Where to fish to land a unicorn: https://ojiudezue.medium.com/where-to-fish-to-land-a-unicorn-in-b2b-saas-9bc93c96152c

• Coda: https://coda.io/

• Atlassian: https://www.atlassian.com/

• Finding high-frequency customers (use cases): https://ojiudezue.medium.com/finding-high-frequency-customers-use-cases-53773a753bb5

• Evernote: https://evernote.com/

• Industry PM conference: https://www.industryconference.com/

• Typeform: https://www.typeform.com/

• Build better products with continuous product discovery | Teresa Torres: https://www.lennyspodcast.com/videos/build-better-products-with-continuous-product-discovery-teresa-torres/

• Pendo: https://www.pendo.io/

• Amplitude: https://amplitude.com/

• Dan Hockenmaier on Twitter: https://twitter.com/danhockenmaier

• Seth Godin’s blog: https://seths.blog/

• A key ritual: Forest time: https://ojiudezue.substack.com/p/a-key-ritual-forest-time

• Principles: https://www.principles.com/

• Dot Collector: https://principlesus.com/dot-collector-real-time-feedback/

• The Halo Effect: . . . and the Eight Other Business Delusions That Deceive Managers: https://www.amazon.com/Halo-Effect-Business-Delusions-Managers/dp/1476784035/

• Dune: https://www.amazon.com/Dune-Penguin-Galaxy-Frank-Herbert/dp/0143111582

• Foundation: https://www.amazon.com/Foundation-3-Book-Boxed-Set-Empire/dp/0593499573

• Foundation on AppleTV+: https://tv.apple.com/us/show/foundation/umc.cmc.5983fipzqbicvrve6jdfep4x3

• Unlox: https://unlox.it/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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

—

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.lennyspodcast.com/behind-the-scenes-of-calendlys-rapid-growth-annie-pearl-cpo/#transcript

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.

Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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.