Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer)

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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

Some takeaways:

1. Monday.com’s culture of radical transparency ensures that every employee has access to real-time metrics, fostering accountability and alignment across the organization.

2. By setting audacious goals—like building 25 features in a single month—monday.com pushes its teams to think creatively and execute at an accelerated pace.

3. The company’s product development philosophy revolves around “impact.” Instead of focusing on shipping features, they prioritize solving real problems that drive business growth.

4. Launching five products simultaneously was a transformative move. It helped them redefine their market positioning and significantly expanded their customer base.

5. Timeboxed development cycles, or “traps,” help the team maintain speed and avoid scope creep, enabling them to deliver faster without compromising quality.

6. As the company scaled, how Daniel learned the importance of delegating effectively, allowing him to focus on high-impact priorities while empowering his team to take ownership.

7. The importance of resilience and self-awareness: by embracing self-doubt and navigating impostor syndrome, he developed mental models to stay grounded and lead effectively.

Where to find Daniel Lereya:

• LinkedIn: https://www.linkedin.com/in/daniel-lereya-aa487646/

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

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/

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/

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.