LLenny's Podcast
← All episodes
Daniel Lereya (Chief Product and Technology Officer)27 April 2025

Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR

7Frameworks
13Insights

Frameworks in this episode

Strategy4 steps

Bold-Move Leap (Not Moving Is the Risk)

When you need a step-change, make the committing bold move all at once — because playing safe is itself the risk

Read →
Strategy5 steps

Competitor-as-Gift Ambition Reset

Turn a competitor's leap into permission to set a goal so ambitious your old way of working can't reach it

Read →
Productivity5 steps

Impact-Over-Output Operating Model

Measure teams by validated impact on customers, not by features shipped — and prove the needle moved

Read →
Leadership4 steps

Radical Transparency Operating System

Share every metric with every employee to put everyone's brains on the challenge, not just their hands

Read →
Productivity4 steps

Scope-by-Time Traps

Box work by a fixed deadline, cut scope to fit, and ship early enough that the feedback is 'this is premature'

Read →
Self-Mastery4 steps

Shed Your Superpowers at Each Scale

The strengths that got you here can become damage at the next phase — constantly re-evaluate what your role actually needs

Read →
Innovation4 steps

Turn the Recurring Break into a Strategic Moat

When the same problem breaks a third time, stop patching — pull your best people off features and solve it for 100x as a competitive edge

Read →

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 3

Hot Take34:30

Radical Transparency: Everyone's Brains in the Challenge

Daniel's most counterintuitive lesson is Monday's radical transparency — before going public, every employee (and even interviewees) could see churn, signups, and paying-account numbers on office dashboards. Family and advisors warned it would demoralize the team when things went south; Daniel found the opposite, describing the loneliness of leadership as 'the dark side of the moon' and arguing shared data gives people a sense of deep partnership.

  • Before IPO, every employee could see paying accounts, churn, and signups; even interviewees saw the dashboards
  • Advisors warned that sharing bad numbers would demoralize the team
  • Daniel calls the isolation of holding information alone 'the dark side of the moon'
  • Transparency puts everyone's brains on the challenge instead of one central brain and many hands
  • As a public company, PMs sign a 10b5-1 auto-sell plan so they can still see the data

“we really want everyone's brains in the challenge and not just one centralized brain and a lot of working hands”

Daniel Lereya · 36:30

“I love to call it the dark side of the moon. you are there alone, right?”

Daniel Lereya · 36:00
#transparency#culture#leadership#metrics
Hot Take45:30

Launching Five Products at Once — Because Playing It Safe Is Risky

Rather than testing a multi-product strategy cautiously on the side, Monday announced five new products simultaneously to force a pivotal leap — despite internal fears about confusing users, hurting conversion, and messy go-to-market. Some products (like Monday CRM) outgrew the core; others were folded back in. Daniel's takeaway: not making bold moves is itself a risk, and leaps often require letting go of what made you successful.

  • Monday was a platform sold with a project-management go-to-market; customers were already building CRMs and dev tools on it
  • They announced five new products at the same time instead of launching one cautiously on the side
  • Internal fears: user confusion, hurt conversion, fragmented go-to-market and pricing
  • Monday sell CRM ended up outgrowing the original product; some products were collapsed back in
  • Launching all five avoided the trap of picking one, having it fail, and concluding multi-product doesn't work

“We actually announced five different new products simultaneously on the same time.”

Daniel Lereya · 47:00

“not taking bold risks not making bold moves it's a risk for itself”

Daniel Lereya · 49:00
#strategy#risk#product#bold-moves
Hot Take57:30

Not Every Customer Feedback Should Drive Your Product

Daniel makes the counterintuitive point that not all customer feedback leads to the best product, and feedback must be taken in context. As an example, early Monday deliberately avoided a free trial so it only heard from customers for whom the product genuinely mattered — using payment as the best proxy for real value and a way to separate the wheat from the chaff.

  • Not every customer's feedback drives you toward the best end product
  • Feedback must always be weighed in context
  • Early Monday chose not to offer a free trial
  • Paying was used as the best proxy that a customer got real value
  • This filtered feedback so the team stayed focused on signal, not noise

“Not every customer feedback is the feedback that will drive you to the you know to the end result of the best product out there.”

Daniel Lereya · 57:30

“we really wanted to hear feedback about our product only from people that the product means something to them.”

Daniel Lereya · 58:00
#customer-feedback#product#pricing#focus

Explainer· 1

Explainer17:30

Why Monday Measures Impact, Not Output

Daniel explains that a great PM is relentless about validating real impact, not shipping features. The PM's first job is to create shared understanding of what would be impactful for customers and how the team will know it moved the needle. Working extremely hard, he stresses, doesn't mean you're succeeding — and sometimes the biggest impact is making existing value more accessible rather than building another feature.

  • A great PM is relentless until impact is validated, not until a feature ships
  • PMs must define the problem/opportunity and how they'll know they moved the needle
  • The whole team succeeds or fails together based on customer value, not just PMs
  • Sometimes the biggest impact is making current value more accessible, not building new features
  • A warning sign: teams saying they'll 'enhance,' 'augment,' or 'extend' value without a measurable change

“So we can work extremely hard. It doesn't mean that we are successful. It doesn't mean that we are doing our work right.”

Daniel Lereya · 21:00

“in some cases doing the biggest impact is not developing another feature it's about making the current value more accessible”

Daniel Lereya · 20:00
#impact#product-management#metrics#goals

Story· 4

Story05:00

The Morning a Competitor Shipped 30 Columns Overnight

Daniel recounts a pivotal early moment when Monday's small team, proud of its execution, discovered a competitor had launched 30 new column types at once — each of Monday's own columns had taken four months to build. Instead of despairing, they treated it as proof it was possible, set an ambitious goal of 25 columns in a month, and shipped 30 within about six weeks by rethinking their architecture.

  • Monday had 5 column types, each taking ~4 months to build, when a competitor launched 30 at once
  • The team took time out of the office to admit their hard work hadn't transformed the product
  • They reframed the competitor's move as a gift proving the goal was achievable
  • An ambitious target (25 columns in a month) forced a totally different way of working
  • They shipped 30 columns about a month and a half later, then repeated the drill for dashboards, widgets, and automations

“We received a gift from our competitors.”

Daniel Lereya · 08:00

“if we're going to add 25 more, multiply it by four months, we're small team. We we're lost.”

Daniel Lereya · 08:30
#product#competition#ambitious-goals#execution
Story22:30

Great Feedback, Tiny Adoption: The AI Blocks Wake-Up Call

Monday shipped AI blocks and got glowing customer feedback, but the daily numbers showed only a few thousand of 250,000 paying companies were actually using AI. The cause: a terms-of-service change gating AI access was scheduled a quarter out. The team pushed legal to move immediately and opened AI to 98% of customers within two weeks — a case where value was real but impact was being throttled elsewhere.

  • Each team tracks a 'daily numbers update' pushed via an internal system called big brain
  • AI blocks let non-technical users (70% of Monday's base) add AI actions with no code
  • Feedback was excellent but only a few thousand of 250,000 paying companies were using AI
  • A planned terms-of-service change was the bottleneck; the team fast-tracked it with legal
  • AI access went from few thousand to 98% of customers in two weeks

“we need to now open it for everyone because this is actually what would be the most impactful thing to do”

Daniel Lereya · 25:30

“we have 250,000 paying companies that use Monday and we saw only like few thousands there”

Daniel Lereya · 25:00
#impact#ai#metrics#adoption
Story1:11:00

Monday DB: Turning a Performance Crisis Into a Moat

When performance issues on Monday's boards spiked for the third time, Daniel decided a band-aid wasn't enough. They pulled a few of their most talented people off features entirely to rethink the data infrastructure at 100x scale — building Monday DB over roughly three years. Released about a year and a half before the interview, it became a core reason Monday is now enterprise-grade, reframing a recurring problem as a strategic competitive edge.

  • Boards grew from ~5 columns and 100 rows to hundreds of columns and tens of thousands of rows
  • Daniel believes performance is the number one feature that makes people use a system
  • After the third performance spike, they stopped patching and rethought the approach
  • Their most talented people were pulled off features to build Monday DB, thinking at 100x scale
  • The goal shifted from fixing an issue to building a competitive edge; it made Monday enterprise-grade

“instead of being like fixing an issue we want this to be our competitive edge”

Daniel Lereya · 1:13:30

“We really believe that performance is the number one feature uh that makes people use your system.”

Daniel Lereya · 1:12:00
#infrastructure#performance#strategy#engineering
Story1:17:30

Reading an MRI and Pricing an AI Product With ChatGPT

Daniel shares two personal examples of leaning on AI. After a knee MRI, instead of waiting five days for a doctor, he uploaded the disc results and asked for a line-by-line explanation — later going to the doctor anyway. On the work side, he independently pulled a full competitive picture on AI pricing in about two hours, work that would normally lean on analysts and PMs. His broader point: the technology is amazing, but productizing it so non-technical people can leverage it is the real challenge.

  • Daniel uploaded his MRI results to AI and asked for a line-by-line explanation before seeing the doctor
  • The value isn't just the answer but being able to keep deep-diving with follow-up questions
  • He built a full competitive perspective on AI pricing in about two hours, independently
  • He uses AI to quickly understand extensive topics like competitor moves and history
  • The gap isn't the technology but productizing it so people can actually leverage it

“how did you think about putting your MRI there and I said I don't know like I just did”

Daniel Lereya · 1:18:30

“just in like two hours I was manag I managed to get a full perspective on what everyone else are doing”

Daniel Lereya · 1:19:30
#ai#tools#productivity#research

Tool· 1

Tool1:23:30

Two Books Daniel Recommends: No Rules Rules and Nonviolent Communication

In the lightning round, Daniel names two books he recommends most. No Rules Rules (Netflix) inspired a lot of Monday's thinking on execution and hiring excellent people, and he gives it to people after discussing culture. Nonviolent Communication, given to him by co-founder Roy, offers practical, judgment-free communication techniques that noticeably changed how he and Roy talk; he shares it with leadership and team members.

  • No Rules Rules by Netflix inspired Monday's approach to execution and excellent people
  • Daniel gives No Rules Rules to people after talking about Monday's culture
  • Nonviolent Communication was given to him by co-founder Roy
  • The book teaches stating facts and feelings without being judgmental
  • Reading it noticeably changed how Daniel and Roy communicate; he shares it with leadership

“The first one I would say is like uh is the No Rules rules book by Netflix.”

Daniel Lereya · 1:23:30

“its name is nonviolent communication and it's about effective ways of communication and understanding the people and their needs”

Daniel Lereya · 1:24:30
#books#culture#communication#leadership

Takeaway· 4

Takeaway15:30

Ambitious Goals Mean Working Smarter, Not Harder

Daniel argues that setting a wildly ambitious goal (cut 4 months to 1 day) is not a demand to work longer hours — that message gets misread as 'work harder.' A goal you literally cannot hit by working the same way forces the team to think differently. He distinguishes fake speed (skipping stages, cutting quality) from real speed, which is understanding what will move the needle and working only on that.

  • A modest goal (4 months to 3 months) reads in people's heads as 'work harder / longer hours'
  • A goal you can't hit even sleeping in the office forces a dramatic change in thinking
  • Fake speed = doing the same work by skipping stages or dropping quality
  • Real speed = understanding what moves the needle and working only on that

“And this is not the message here. It's about working smarter.”

Daniel Lereya · 16:00

“there's fake speed, which means trying to do the same work by skipping stages or not doing the high quality that you want. But there's…”

Daniel Lereya · 16:30
#goals#execution#focus#leadership
Takeaway51:00

Scope by Time, Not Effort — And Ship Before It's Ready

Daniel warns that more time spent on a product usually creates more questions, complications, and invented assumptions about user needs. He advocates setting time-boxed 'traps' (e.g. three weeks, or ship by the next earnings) to force focus on the core value. Getting a first version to real users fast — even if the feedback is 'this is premature' — is priceless and beats spending 'one, two, three more weeks' chasing a better product.

  • Spending more time often yields more questions and invented assumptions, not a better product
  • Time-boxing ('traps') forces teams to focus on the real core of the value
  • Even as a public company Monday sets traps like shipping by the next earnings call
  • A first version getting 'premature' or imperfect feedback is a good sign it was focused enough
  • Building too much risks 'death by a thousand cuts' as every corner gets over-built

“thinking if I just have one, two, three more weeks, I will build a better product. I think it's not it's not true.”

Daniel Lereya · 54:00

“we have three weeks let's think about it and scope it by time it makes you extremely focused”

Daniel Lereya · 52:30
#shipping#time-boxing#focus#product
Takeaway1:00:00

Your Superpower Can Become a Liability at Scale

Daniel's most personal lesson: what made him successful in one phase wasn't what he needed in the next. His strength of mastering every detail and holding everything in his head added value when Monday was small but became damaging as it grew. He learned this partly when a colleague told him after an articulate leadership review that they 'didn't understand anything' — a signal he needed to communicate the three most meaningful things, not everything.

  • Daniel's role changed dozens of times inside one company as it scaled
  • Mastering all the details and holding everything in his head helped when small, hurt at scale
  • Letting go of a perceived superpower is frightening but necessary
  • A colleague told him after a QBR that they 'didn't understand anything' despite his articulate delivery
  • The colleague only wanted the three most meaningful things he was facing, not everything

“what got me to this phase is is not necessarily what's going to make me successful in the next phase”

Daniel Lereya · 1:00:30

“one of my colleagues in the core leadership team said I didn't understand anything like what is the bottom line of all of this”

Daniel Lereya · 1:03:00
#leadership#scaling#communication#personal-growth
Takeaway1:05:00

Everyone Feels It: Being Vulnerable While You Lead

Daniel opens up about the emotional reality of the journey — asking whether he was the right person to lead a company worth billions, swinging from elation to the lowest point in a single day. His reassurance is that everyone feels this. He recommends staying confident yet vulnerable enough to learn, and running a personal exercise of looking back six months from now to force continued growth.

  • Daniel repeatedly asked whether he was the right person to lead the company at each phase
  • A co-founder reminded him that as the one who built it, no one could do it like him
  • You can be super happy and at the lowest point on the same day
  • His reassurance: if you're feeling it, you're not alone — everyone feels it
  • He uses a mental exercise: imagine looking back in six months on what he learned and evolved

“if you're feeling it you're not the only one everyone are feeling it”

Daniel Lereya · 1:06:30

“be confident about yourself be vulnerable in order to learn and to evolve”

Daniel Lereya · 1:07:00
#leadership#vulnerability#imposter-syndrome#personal-growth