Eran Zinman, Co-Founder & Co-CEO @Monday.com: Going Upmarket, International and Multi-Product |E1247
Eran Zinman (guest), Harry Stebbings (host), Harry Stebbings (host), Narrator
In this episode of The Twenty Minute VC, featuring Eran Zinman and Harry Stebbings, Eran Zinman, Co-Founder & Co-CEO @Monday.com: Going Upmarket, International and Multi-Product |E1247 explores from DaPulse to $1B ARR: Monday.com’s Playbook for Relentless Scale Eran Zinman, Co-Founder & Co-CEO of Monday.com, shares how early failure, product pivots, and an obsessive test‑and‑learn culture shaped Monday’s path from a small communication tool into a $1B+ ARR multi-product platform.
From DaPulse to $1B ARR: Monday.com’s Playbook for Relentless Scale
Eran Zinman, Co-Founder & Co-CEO of Monday.com, shares how early failure, product pivots, and an obsessive test‑and‑learn culture shaped Monday’s path from a small communication tool into a $1B+ ARR multi-product platform.
He explains how they moved from pure PLG and low-ACV SMB customers to adding a large sales organization and going upmarket, all while maintaining strong cash-flow discipline via an in-house performance marketing engine, BigBrain.
Zinman details Monday’s horizontal-to-vertical evolution, including the rise of Monday CRM, Dev, and Service, and how customer behavior on the core platform directly informed their multi-product strategy.
He also discusses co-CEO dynamics, board management, personal focus and mental health, and why he sees AI as an accelerant—not a threat—to horizontal software like Monday.
Key Takeaways
Treat failure as a necessary input, not an outcome to avoid.
Zinman’s first startup failed largely because he feared negative feedback and delayed launch for 14–15 months; he reversed this at Monday by institutionalizing rapid shipping, A/B testing, and aggressive customer feedback loops.
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Pivot based on customer reality, not your next feature idea.
After burning 70–80% of their seed money on a communication tool with weak pull, the founders stopped coding, interviewed customers deeply, and pivoted to flexible work management—unlocking true product-market fit.
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Optimize for cash efficiency early, not just SaaS vanity metrics.
Monday built BigBrain in-house to track every click and cohort, then designed campaigns, billing terms, and onboarding around cash payback velocity, effectively recycling ~$5M of marketing spend into a ~$15M budget and embedding cash discipline into the culture.
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Use PLG to earn the right to add sales, not to avoid it.
They grew to roughly $40–60M ARR on PLG before adding sales, realizing that expansion, governance, and enterprise needs required human relationships and processes—eventually building a 1,000+ person sales org without abandoning SMB.
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Let customers reveal your next products, then build business units around them.
Tens of thousands of accounts built DIY CRMs, dev and service workflows atop Monday’s flexible boards; this demand led to packaging vertical products (CRM, Dev, Service) on the same platform, each with dedicated GTM and product teams like startups inside the company.
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In crowded categories, differentiation is in model and UX, not existence.
Rather than fearing Salesforce, HubSpot, Jira, or ServiceNow, Monday leaned into flexibility, ease-of-use, and cross-product data flows as its wedge, betting that customers want control and configurability without enterprise-level complexity.
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Founder effectiveness compounds when you fix the hardest, most avoided problems first.
Zinman argues founders naturally avoid the most painful issues; he intentionally prioritizes those, and invests in his own health, therapy, and routines (sleep, exercise, family time) to stay clear-headed enough to tackle them.
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Notable Quotes
“The reason I failed in that company is that I was afraid to fail.”
— Eran Zinman
“From day one, we didn’t build a product; we built a platform.”
— Eran Zinman
“We always felt we were one feature away—until we realized it wasn’t about the next feature, it was about talking to customers.”
— Eran Zinman
“Our customers have been the biggest investor in Monday—more money than we ever raised from VCs.”
— Eran Zinman
“I should treat myself like a professional athlete. I need to be at my peak to take care of the company.”
— Eran Zinman
Questions Answered in This Episode
How would Monday’s growth trajectory have changed if they hadn’t built BigBrain in-house and instead relied on standard analytics tools?
Eran Zinman, Co-Founder & Co-CEO of Monday. ...
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At what point does adding more products on the same platform risk diluting focus or confusing customers, and how does Monday guard against that?
He explains how they moved from pure PLG and low-ACV SMB customers to adding a large sales organization and going upmarket, all while maintaining strong cash-flow discipline via an in-house performance marketing engine, BigBrain.
Get the full analysis with uListen AI
How can early-stage founders practically measure when PLG alone has hit its limit and it’s time to invest in sales and enterprise capabilities?
Zinman details Monday’s horizontal-to-vertical evolution, including the rise of Monday CRM, Dev, and Service, and how customer behavior on the core platform directly informed their multi-product strategy.
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In a future dominated by AI agents, what new features or roles should a horizontal system-of-record like Monday prioritize to stay central to workflows?
He also discusses co-CEO dynamics, board management, personal focus and mental health, and why he sees AI as an accelerant—not a threat—to horizontal software like Monday.
Get the full analysis with uListen AI
What governance or cultural mechanisms keep multiple semi-autonomous product business units aligned with a single brand and platform strategy?
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Transcript Preview
It was still hard for us to raise funds back in the days, because people didn't get the idea. We grew from 6 million of ARR to 18 the year after, and then from 18 to 50, and 50 to 120, you know, in three years. 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.
Ready to go? (instrumental music plays) Eran, I am so excited for this. I- I heard so many great things from Avi, from Nino, from Rajiv. I spoke to pretty much the whole cap table. It was a lot of fun. But thank you so much for joining me today.
Thanks for having me. I'm excited for this.
Oh, so am I. Listen, I've wanted to do it for a while. I'm like the biggest Monday nerd.
(laughs)
I love SaaS. Uh, many reasons why I'm m- just per- per- perpetually single. Um, but I wanna start, I heard you're a really great video game player.
Oh, wow.
And this is a commonality in great founders that I've interviewed. So why are video games correlated to success in founders?
Oh, wow. You- you've really done your research, huh? That's, um-
Yeah.
Yeah.
Yeah, I told you. (laughs)
Um, yeah. I- I actually, I l- I love video games. I actually play to this day. So, uh, it's been an old habit of mine just as a- as a kid, uh, which I still keep. Uh, but, um, when I was young, I used to play a lot of strategy games. Um, one of my favorites ever was, um, I don't know, uh, if you remember, uh, but it was called, uh, Command & Conquer, uh, Red Alert 2.
Yeah. Yeah, yeah.
It's a- it's a strategy game. And, um, I think if- if you play the right games, you can learn a lot from them, uh, especially strategy games. Because, uh, you, on one hand, you need to see the big picture all the time. Um, you need to understand the strategy, you need to understand what's going on, but also handle the tactics, uh, know all the details, act quickly, and I think that's, uh, kinda similar in business, I guess, uh, to some extent.
Totally is. I- I remember Tobi at Shopify saying to me that he, uh, he thought that it was more relevant if you had, like, managed clans in games before-
(laughs)
... than if you'd been to university, I think. And I thought that was rather apt. (laughs)
I agree. It's as hard as- as- as doing that in- in business.
Now, dude, you know, Monday is not your first business. And I remember after your first business, you said something which is, "Failing is part of our success." And I just wanna dive into this, because I think it's important. What have you learned about embracing failure over the years, and how do you think about that statement?
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