Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer)
Lenny's Podcast: Product | Growth | Career
Lenny Rachitsky
5 • 1.5K Ratings
🗓️ 27 April 2025
⏱️ 92 minutes
🧾️ Download transcript
Summary
Daniel Lereya, the Chief Product and Technology Officer at monday.com, shares how he and his team realized they were being outpaced by competitors and how that realization completely transformed how they operate and allowed them to build a global powerhouse, doing over $1 billion in ARR, with 245,000 customers worldwide.
What you’ll learn:
1. How they used seemingly impossible goals, like building 25 new features in one month, to unlock bigger thinking on their team
2. How sharing real-time metrics with the entire company—even during interviews—created a culture of accountability and alignment
3. How focusing on impact, rather than just shipping features, has transformed the company’s culture
4. The story behind monday.com’s decision to launch five new products simultaneously and how it redefined their market positioning
5. How they use “traps” (timeboxed deadlines) to drive focus, avoid scope creep, and deliver faster
6. Daniel’s personal journey of navigating impostor syndrome and scaling challenges, and the mental models he uses to stay grounded and effective
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Brought to you by:
• Enterpret—Transform customer feedback into product growth
• Airtable ProductCentral—Launch to new heights with a unified system for product development
• Vanta—Automate compliance. Simplify security
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Where to find Daniel Lereya:
• LinkedIn: https://www.linkedin.com/in/daniel-lereya-aa487646/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Daniel and monday.com
(04:20) The pivotal moment: competitors shipping faster
(08:50) Setting ambitious goals
(17:44) Focusing on impact rather than features
(27:07) Transforming your product quarterly
(32:07) Scaling monday.com: challenges and strategies
(39:14) How monday.com maintains transparency as a public company
(45:40) The importance of taking risks
(51:02) Counterintuitive lessons in product development
(54:33) The value of timeboxing and deadlines
(57:28) Embracing user feedback
(59:54) Adapting leadership styles
(01:04:43) Personal reflections on leadership
(01:10:41) Handling crises and strategic planning
(01:17:28) The role of AI in work and personal life
(01:22:13) Final thoughts and lightning round
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Referenced:
• Monday.com: https://monday.com/
• The basics of a monday.com board: https://support.monday.com/hc/en-us/articles/115005317249-The-basics-of-a-board
• Eran Zinman on LinkedIn: https://www.linkedin.com/in/eranzinman/
• Roy Mann on LinkedIn: https://www.linkedin.com/in/manroy/
• Tal Harari on LinkedIn: https://www.linkedin.com/in/tal-harari-a2515215/
• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile
• A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals): https://www.lennysnewsletter.com/p/shape-up-ryan-singer
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• AI blocks: https://support.monday.com/hc/en-us/articles/18433811274386-AI-Automation-blocks
• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of
• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox
• SpaceX: https://www.spacex.com/
• Why and how to lead with transparency: https://monday.com/blog/monday-insights/may-30th/
• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra
• This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your data scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome
• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/
• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/
• ChatGPT: https://chatgpt.com/
• Cursor: https://www.cursor.com/
• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin
• FIFA 22: https://store.playstation.com/en-us/concept/10002538/
• Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890
• Google Photos: https://photos.google.com/
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Recommended books:
• Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp.com/shapeup
• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595
• No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860
• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X/
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
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Lenny may be an investor in the companies discussed.
Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
Transcript
Click on a timestamp to play from that location
| 0:00.0 | A great PM basically for me is someone that is relentless until he gets this impact, until |
| 0:05.5 | he validates that this impact is in place. |
| 0:08.5 | In some cases, doing the biggest impact is not developing another feature. |
| 0:12.9 | It's about making the current value more accessible. |
| 0:15.7 | You've been at this for eight years. |
| 0:17.3 | You said there's 250,000 customers at this point. |
| 0:20.4 | What would you say is the most counterintuitive thing you've learned through this journey of Building Monday? |
| 0:25.5 | We really have an approach of very radical transparency about everything. |
| 0:30.9 | Before we went public, we actually shared every bit of information with our employees. |
| 0:36.7 | Instead of demoralizing people, I think that this is something that gives them a sense of deep partnership. |
| 0:41.3 | We really want everyone's brains in the challenge and not just one centralized brain and a lot of working hands. |
| 0:48.3 | You basically realized that your competitors were shipping a lot faster than you were. |
| 0:54.2 | That made you shift the way you think about product and the way you operate. |
| 0:57.5 | Some of our competitors did something that we can only imagine. |
| 1:01.1 | We said, OK, we need to treat it differently. |
| 1:03.2 | We received the gift from our competitors. |
| 1:05.5 | They showed us that it's possible. |
| 1:07.5 | Use your competition, know it, and take it, and set ambitious goals and believe in |
| 1:11.4 | yourself, and you can do amazing things. |
| 1:14.5 | Today, my guest is Daniel Larea. Daniel's currently chief product and technology officer at |
| 1:19.5 | Monday.com. He joined when they were just around 40 employees. And a few years in, Daniel and |
| 1:24.8 | the exec team realized that their competitors were able to move a lot faster than they were and ship a lot more often than they were. |
... |
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