Jan 17, 2025 · 1h 1m · news
Eran Zinman, Co-Founder & Co-CEO @Monday.com: Going Upmarket, International and Multi-Product |E1247 · 20VC with Harry Stebbings
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In this 20VC interview, Monday.com Co-Founder and Co-CEO Eran Zinman shares the company's journey from its early product pivots and data-driven marketing scale-up to going public and navigating the unique dynamics of a co-CEO partnership.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 21.5% of the talking time here. How this is scored →
Harry as informed peer 3.6 Guest teaching 4.6 Guest disagreement 1.5 Harry pushing back 2.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 33:44 Rejection of wasted marketing channels
When Harry presses Eran to admit which advertising channel was a waste of money, Eran directly rejects the premise, countering that channels shouldn't be judged on simple effectiveness because different platforms serve entirely different user intents.
Hardest push from Harry ▶ 53:08 Host pushes back on complete email abstinenceAfter Eran claims he does not use email, Harry explicitly refuses to buy the assertion without clarification, pressing Eran on how external stakeholders like investors and customers can possibly be managed without email.
Biggest teaching moment ▶ 37:48 Clarifying Monday as a generic platformEran educates Harry and investors on a fundamental misconception, explaining that Monday was never built as a rigid work management tool but rather as an underlying generic platform similar to Salesforce's force.com.
Harry holds his own ▶ 16:11 Host detailing VC heuristics against SMB modelsHarry takes full command of the discussion by detailing the precise venture capital heuristics regarding low ACV, PLG constraints, and the traditional inability to monetize SMB customers effectively.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Strategy of Video Games and Founder Success | 4 | 3 | 1 | 1 | Harry opens with well-researched personal background questions on strategy video games, drawing parallels to Shopify founder quotes. Eran agrees with the framing and shares lessons learned from early gaming and initial startup failures. | |
| The Hardest Failures to Accept | 2 | 4 | 1 | 1 | Eran elaborates on overcoming the fear of failure and transitioning into founding Dapulse. Harry acts as a supportive interviewer guiding the backstory without challenging the narrative. | |
| The Pivot to Flexible Work Management | 3 | 4 | 1 | 2 | Harry asks how founders should distinguish between persistence and knowing when to pivot. Eran explains how spending 80 percent of their seed round forced them to stop coding and talk directly to customers. | |
| The Self-Serve 'Woohoo' Machine | 3 | 4 | 0 | 1 | Eran shares a lighthearted anecdote about installing a dashboard TV with a woohoo sound effect to track self-serve signups. Harry probes into pricing models and initial customer acquisition dynamics. | |
| Facebook Performance Marketing and Runway Crunch | 3 | 4 | 1 | 2 | Eran details early performance marketing on Facebook and how investor support extended their runway during a tight capital crunch. Harry tracks the narrative and asks focused follow-up questions. | |
| Investor Skepticism in the Series A | 7 | 4 | 2 | 6 | Harry demonstrates strong venture capital expertise by articulating the exact negative investor heuristics around low ACV and selling to non-tech SMBs. Eran acknowledges the critique while explaining how they overcame skepticism. | |
| The Big Brain Marketing Engine and Cash Flow | 3 | 6 | 1 | 2 | Eran educates the audience on optimizing for cash flow over standard SaaS metrics like LTV and CAC through internal tools like Big Brain. Harry asks how they constructed their cash cycle velocity. | |
| Insight Partners and the Series B | 4 | 5 | 2 | 4 | Harry questions standard startup wisdom regarding waiting to be pulled upmarket vs actively hiring a sales team. Eran details how adding sales allowed them to go upmarket without abandoning SMBs. | |
| The Enterprise Pyramid and Hyperscaling | 4 | 5 | 1 | 2 | Eran outlines the enterprise pyramid strategy and recount taking Jason Lemkin benchmark growth numbers literally. Harry brings up industry anecdotes while probing into scaling challenges. | |
| The Road to One Billion | 5 | 5 | 1 | 2 | Harry demonstrates thorough prep by citing precise 2023 monthly spend statistics on performance marketing. Eran explains how they created the internal road to one billion dashboard to align the company. | |
| Optimizing YouTube and Facebook | 4 | 6 | 4 | 4 | Harry repeatedly tries to get Eran to name an ad channel that was an ineffective waste of money. Eran rejects the premise entirely, explaining that different channels simply serve different user intents. | |
| Building a Generic Platform, Not a Tool | 4 | 6 | 1 | 2 | Eran clarifies that investors misunderstood Monday by treating it as a project tool when it was architected as a force.com equivalent generic platform. Harry inquires about organizational design across multi-product lines. | |
| Disrupting Competitive Markets | 5 | 5 | 4 | 5 | Harry challenges Monday's defensibility against intense CRM competition and potential AI agent disintermediation. Eran forcefully argues that systems of record remain essential even in an AI-driven workflow. | |
| The Anticlimactic IPO Day | 3 | 4 | 1 | 2 | Eran paints a vivid picture of the empty Nasdaq building on IPO day and walking back to his hotel in a white t-shirt. Harry compares the emotional release to endurance athletes finishing a race. | |
| The Co-CEO Dynamic | 3 | 5 | 1 | 2 | Harry questions how the co-CEO setup works without conflict. Eran explains how a shared lack of ego and daily walks home enable seamless board and operational management. | |
| Quick Fire: Goal Setting and Email Abstinence | 3 | 5 | 3 | 6 | When Eran states he refrains from using email entirely, Harry actively pushes back on how that is practical when dealing with external board members and investors. Eran clarifies that his team handles scheduling emails so he can maintain deep focus. | |
| Quick Fire: Mentors, Upbringing, and Defining Success | 2 | 3 | 1 | 1 | Eran shares reflective thoughts on upbringing, parenting, and defining success beyond metrics. Harry ends with light banter before concluding a warm and open conversation. |
Statements from this episode (46)
Monday.com scaled ARR from $6M to $120M in three years
“We grew from six million of ARR to 18 the year after, and then from 18 to 50, and 50 to 120, you know, in three years.”
Founders should address business problems precisely when they become most painful
“What I found about Founders is that you try to avoid the hardest things in your business. If something is very painful, that's the right time to get into it and fix it.”
Zinman's first startup failed after 15 months of building without capital
“Like I built a product and I worked at it for about 14 or 15 months before launching it. And after 14 or 15 months, I didn't raise any money. I just felt I wasn't ready. It was a big failure. Like I ran out of money, personal money and ran out of energy.”
Early mockups yield the same feedback as 14 months of building
“Because after 14 months working on that product, people gave me feedback that if I've shown them like a mock-up or like an earlier version, I would get the same feedback and I would be in a totally different place today.”
Personal credentials do not matter when building products for real users
“When you build an actual product that people need to use, nobody care about your achievement or knowledge or how much you know about anything. It's all about the product.”
Software platforms should offer flexible tools rather than rigid workflows
“I don't know what's the best way to manage a team or a group of people or, you know, a business, but I can give people the tools to do it and they know what's best for their business. So from day one, we said we don't know exactly what's the solution for every…”
Communication tools are nice-to-haves, not core work management software
“So we initially thought that it will be more focused around communication and collaboration, but one thing that we found is that a lot of those tools are under the category of You know, yeah, we can use it, but it's a nice to have tool. It's not something that…”
Monday.com spent 80% of its seed funding before pivoting
“And, you know, after you know, we kind of spend like 70 or 80% of our seed round, we sat down and said to ourselves, look, something is not working.”
Wix was one of Monday.com's first three paying customers
“When we had, like, the initial version of the collaboration tool, we had about three or four paying customers. One of them was Wix.”
70% of Monday.com's customers are non-tech companies
“And up until today, 70% of our customers are actually non-tech companies and that, that's amazing because it just opens up the TAM and the audience of the company so much.”
Entree Capital extended a convertible note when Monday.com's seed round ran low
“I give a lot of credit to our board members specifically. You mentioned Avi you know, I would say the typical investor seeing that a company spent 80% of their seed round and didn't reach, like, product market fit, you know, maybe would kind of give up on the …”
Monday.com raised a $1.4M seed round at a $2M pre-money valuation
“We raised 1.4 million for at I think it was two million pre. So that, yeah, that's back in the days. Good times. Yeah. For investors. Yeah. 30% of the company.”
Monday.com faced widespread investor rejections during its Series A, B, and C
“We got a lot of no's. I was, I would tell you that in our A, B and C rounds.”
Standard SaaS metrics optimize for accounting rather than actual cash flow
“If you think about standard SaaS metrics like LTV, CAC ARR, whatever, they never mention cash. Like, it's not about cash. It's like more about around accounting and predictability, but we always try to optimize for cash.”
Monday.com recycled $5M of venture capital into a $15M marketing budget
“So we actually managed to turn five million of money raised from investors into a 15,000,001 five performance marketing budget. So we built a very efficient machine that recycles money and kind of reinvested that back into the business.”
Monday.com's customers provided more funding than all its venture capital combined
“I think our customers has been the biggest investor of Monday. More money than we ever raised from investors.”
Monday.com had $3M to $4M ARR when raising its Series A
“I don't remember exactly, but I would say around probably three or four million of ARR.”
Monday.com reached $7M ARR before raising its Series B
“I think when we raised that round, we had like seven million of ARR.”
Monday.com has expanded its sales organization to over 1,000 people
“We built an amazing sales team, you know, going forward to today where we have more than a thousand people in our sales team, but it was not obvious back in the days.”
Hiring a great VP of Sales to sell a bad product is a curse
“I think that if you start as a small company and you have a, an amazing VP of sales, you know, they can sell anything, even if your product is really crappy. That's a curse. It's not something positive”
Monday.com waited until $40M to $60M ARR to add a sales team
“I think it was 40 or fifty million, maybe even 60 that we kind of added the sales team.”
Monday.com Co-CEO Eran Zinman does not use email
“I, one of the reasons I didn't reply to your email is that I don't use email”
Monday.com aimed for $1B ARR by 2023, missing the goal by one year
“When we got to 50, we built a dashboard. Of the road to, we call it the road to one billion. We built it like a vertical TV in the office showing that we want to reach one billion by the year of twenty-twenty-three. We actually missed it by one year”
At $1B ARR, SaaS growth must come mostly from existing accounts
“When you reach one billion and you want to grow 30%, you have majority of revenue need to come from existing customers.”
Monday.com spent nearly $17M per month on performance marketing in 2023
“Yeah. Something like that. A little bit less, but around that.”
Monday.com operates at an over 25% free cash flow margin
“We're very efficient in terms of cash flow, you know, over 25% free cash flow positive.”
Facebook advertising fundamentally changed Monday.com's growth trajectory
“Facebook was amazing for us because I think it just changed the trajectory of the company.”
Monday.com's CRM is growing faster than the original platform did
“You know, the CRM today is growing faster than what Monday did back in the days.”
Monday.com's CRM product grew from zero to $25M revenue in one year
“It wouldn't disclose this on a quarterly basis, but the last invested investor day which was last year it was growing from almost zero to twenty five million in, in one year.”
Monday.com was built as a generic platform, not project management software
“We didn't build a work management or project management tool from day one. You know, the equivalent, we built the equivalent of force.com. Which is for Salesforce. We built a generic platform, not about work management, not about CRM, just the building blocks.”
Companies will consolidate core SaaS tools onto Monday.com
“Eventually I see, definitely see a future We're accompanied by several tools and consolidate on Monday for the core business use cases, whether it's CRM, work management, that service, and the compound value of using several of those tools, the flow of data, a…”
Multi-product expansion requires distinct go-to-market strategies for each product
“Maybe one lesson is it's not just about the product itself. Go to market is as important and every product has a very different go to market. It's unbelievable. It's so different. Different buying dynamics, different buyer, different decision process, differen…”
Monday.com operates independent, startup-like business units for each product line
“Yeah, that's exactly how we think about this. We have different business units dedicated for each product. Every product is in different phase. So, you know, CRM is more mature and then dev and then service and obviously work management is kind of the most mat…”
CRM and Dev products will become dominant revenue drivers for Monday.com
“Definitely CRM will be very dominant going forward. Dev as well.”
Zinman avoids reading competitor news to prevent founder anxiety
“When I built my first startup I remember that I used to log in to, you know, TechCrunch or read tech news, and every time I saw a competitor that I felt was competing with me, I felt this weird feeling in my stomach, and then I swore to myself, and I'm never g…”
SaaS tools will remain essential despite AI agent automation
“I don't think that, you know, SAS tools will go away. I think if anything, some of the work can be replaced by AI, but still the fundamental principle of why those tools exist is, is strong and will remain going forward.”
AI will force SaaS pricing models to shift from seats to consumption
“For sure. You know, I think a lot of SaaS tools have been very focused on seed count and, you know, once you replace, you know, human labor with AI functionality pricing should adjust and maybe be more focused on consumption in addition to seeds.”
Public market investors are far more sophisticated than private market investors
“Public market investors really surprised me. They are way more sophisticated than what I thought. I thought that initially when we went public, I thought that, you know, it's all about the private market, those investors, but public market investors are super …”
Quarterly earnings reports improve operational cadence for public companies
“I think that cadence of quarterly, you know, earning reports really add a great cadence to the company.”
Monday.com's co-CEOs walk home together daily in Tel Aviv to brainstorm
“We actually, we walk home every day, like walking. We live in Tel Aviv, so we walk every day. We spend hours just to think and talk about things.”
Monday.com sent automated daily performance metrics via SMS to its board
“Actually, one of the things we built into BigBrain is I don't know if Avi told you, but we used to send every day, like a daily SMS of the company performance every day to our board members. Whether it was good or bad, it was automatic.”
Align board members individually before meetings to avoid ego fights
“And if we had something that we wanted to make a decision about, we always talk with each one of them individually before the meeting, because the last thing you want is to get into an ego fight. So just get their opinions and change the things before the meet…”
Goal setting should start with top-down targets, not bottom-up limits
“Maybe something that's not intuitive is about setting goals. Most people, when they set goals, they try to figure out what they can do. I never think about it this way. I'm thinking about what I want to achieve and then try to figure out a way to do it because…”