[BidClub_]
20VC · · 70 min

Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Eran Zinman

Eran ZinmanHarry Stebbings

YouTube
TL;DR
  • The market is pricing Monday.com as if the pivot fails: at the post-earnings low of $70, market cap was ~$3.7B against ~$1.5B cash, no debt, and over $1.3B ARR — roughly a 1.5x EV/ARR multiple. Eran Zinman's reaction was relief, not despair: "What the market is saying to me is the company is worth zero. Okay, fine. Now I need to build… Screw it. I'm going to go all in."
  • Of the three SaaS doomsday scenarios discussed, Zinman dismisses two and acknowledges the third as a real risk if companies fail to change. Vibe coding is "my least favorite one" (UI ≠ maintainable org-wide software), LLM providers eating the app layer fails the AWS precedent — but on systems of record becoming databases: "It's a tough one because it's true… Nobody will want to buy software that not doing the majority of the work for them."
  • His core reframe: software has delivered the same value for 25 years while 90% of the work happened outside the tool; AI flips that to doing 70-80% of the work, so software TAM "is going to be 100x" as spend migrates from headcount (60-70% of a Monday-like company's expenses) to software (7-8% today). CEOs will "gladly" pay for software that replaces hiring.
  • The AI receipts inside Monday are specific: the qualification work formerly handled by ~100 SDRs is now 100% done by agents, with those SDRs moved to outbound (response time 24 hours → 3 minutes, conversion and booking rates all up), support AI-run, every developer on Claude Code and Cursor. Yet Harry's pushback lands — headcount is still growing mid-teens (down from a planned 20%), and Zinman only commits to roughly flat 3,000 employees by 2030 versus Klarna's 7,000→2,000 trajectory.
  • The pivot is total: biggest transformation since the 2013 launch — product, go-to-market, and pricing moving from seats to hybrid to "eventually 100% consumption." The bet is horizontal orchestration between humans and agents ("if you haven't built an agent on Monday, you're not using the product properly"), plus CRM and service rebuilt from scratch, fully agentic: "Service dominated by ServiceNow, CRM dominated by Salesforce is open market today."
  • Actual AI damage to the business so far is narrow and quantified: Google's AI mode in search cost ~10% of new-ARR acquisition (high-intent SMB clicks on sponsored links); the other 70 channels saw no impact, and gross retention is the highest ever.
  • Skin in the game and capital discipline: an $870M buyback underway, Zinman still holding ~80% of his shares 14 years in, no interest in going private (27% free cash flow, no need to raise). On picking between "OpenAI at 500 or Anthropic at 380," he reaches for 1998: "Yahoo and Netscape going to suck all the value from the internet revolution — and we know nothing… we're probably missing 90% of the picture," though "Anthropic have a little bit more momentum right now."
Digest · the substance, structured for research

1. The sentiment crashed; the business didn't

  • Monday.com sits near $1.3B in revenue yet trades at $3.9B, and Zinman's opening move is to split the two phenomena: earnings calls look "kind of normal, some companies are even exceeding expectations," while sentiment shifted "very aggressive, very powerful" in the last six months — "every day there's a new doomsday scenario, a new tweet." He's careful not to dismiss it: "there's a lot of truth to that."
  • Nor is Monday unique — ServiceNow is down 50%, Salesforce down 60%. His read of what investors actually want: given "infinite demand for AI products," there shouldn't be a demand problem, so "you need to prove to us that you can supply that demand… we want to see acceleration of revenue. And they're right."

2. Doomsday #1, vibe coding — the one he rates least

  • Harry raised one apocalypse scenario; Zinman volunteered the taxonomy: "there's like five doomsday scenarios I'm familiar with." Harry joked he could come up with an additional three. The three discussed: everyone vibe-codes their own apps, LLM companies capture enterprise software, platforms decay into systems of record.
  • On the CNBC journalist who vibe-coded her own Monday live on air (he found out from a flood of messages as he was going to bed): "she could have done it for Salesforce or ServiceNow, or created a search engine." His distinction — "a big difference between vibe coding a user interface and building actual software that works across an organization"; people underestimate maintaining software over time, and a dedicated person or team vibe-coding apps can be a huge cost compared with software, which is a small expense for most companies.
  • His reductio: if you could vibe-code any company, no startup would have value — yet Ramp just raised at $30B, while Harvey and Legora are also cited. Harry's pushback: those are trained on proprietary legal data you can't replicate. Zinman doesn't concede it: "you can probably get the vast majority of the value even without that specific training." Verdict: "From all the theories of how software is going to be disrupted, this is my least favorite one."

3. Doomsday #2 — LLM providers won't eat the app layer, per the AWS precedent

  • The history lesson he leans on: when Amazon built AWS, "everybody said Amazon is going to capture all enterprise software value" because servers were the heavy lifting. "What really happened is the exact opposite" — a boom of companies built on top. LLMs are that infrastructure again, and he expects "an excess of software built on top of the LLM, not less — exponentially more."
  • The mechanics argument: enterprise is "a whole different business" — different sales process, no pure PLG for org-wide deployment, buyers "want to be handheld" — and the labs have a bigger prize chasing the infrastructure layer. "No company on earth, with AI or without, can do everything."
  • Harry agrees this is the weakest doomsday: Anthropic moving into security replacing CrowdStrike or Palo Alto is "a very weak argument" — though he can't resist "Dario just killed my CrowdStrike over the weekend. Thanks, Dario. Cheers."

4. Doomsday #3 is the real one: "It's tough because it's true"

  • No deflection here — "I believe that with all my heart." His frame: software's value hasn't changed in 25 years, from his DOS days onward — a database, dashboards, some workflows. 90% of the work always happened outside the tool: the salesperson makes the call, builds the deck, preps outside the CRM, and only tracks the result inside it.
  • AI flips the equation — it "can potentially do 70-80% of the work, and not 10-20% like it used to be." The consequence, stated flat: "Nobody will want to buy software that not doing the majority of the work for them — otherwise you're just buying legacy software."
  • His reading of the sell-off is unusually charitable: the market understands the value is changing but "doesn't know which company will be able to change — and we're out until we get that confidence. And I get it, because change is extremely hard, especially for an existing company."

5. The 100x TAM claim — and the headcount paradox Harry wouldn't drop

  • The bull math, from Zinman's Monday example: on ~$1B of expenses, 60-70% goes to headcount and 7-8% to software. If businesses scale on software instead of hiring, "every CEO will be gladly increasing the expense on software," and "the TAM of software is going to be 100x from what it is today… the opportunity in the software market today is like we've never seen before in our lives."
  • Harry's pushback — worth keeping: Monday's own analyst day showed 20% year-on-year headcount growth for '26. "Is that not completely paradoxical?" Zinman's concession: it's been cut to mid-teens, "we might even take it lower… but I don't want to press the brakes violently" during the transition.
  • Pressed against Klarna's Seb (7,000 → 3,000 → 2,000 by 2030), Zinman says Monday's ~3,000 today will "probably not grow substantially" by 2030 — but reframes: slashing headcount won't change investor perception. "This is the biggest opportunity in software ever in our lifetime… what I want to do is capture as much as I can out of it."

6. What AI already runs inside Monday

  • The qualification work formerly handled by ~100 SDRs is now 100% done by agents, with those SDRs moved to outbound. The stats: callback time went from 24 hours to 3 minutes, missed calls collapsed, "conversion rate went up, people answering went up, opportunity-to-book went up — all parameters went up. AI speaks all languages, available 24/7." They built the SDR system in-house; support is a mix of third-party and homegrown, because "you still need to highly customize tools today."
  • All developers are on Claude Code and Cursor — the choice between them "right now it's a sense of flavor." Output is up, but honestly hedged: "there's new bottlenecks you find each time you increase one of those productivities" that aren't attached to writing code.
  • The confession that frames the whole pivot: for the first stretch after ChatGPT, "we sprinkled some AI dust on top of our product" — AI formulas, AI blocks, AI columns — "it was sugar coating… the value haven't changed." The light-bulb moment came only about a year ago, "not one tweet or one product — a collective understanding that things are changing forever."

7. The pivot: orchestrating humans and agents, priced on consumption

  • "It's the biggest moment for us in the history of the company" since the 2013 launch — product, go-to-market, homepage, ads, and pricing all change. On pricing his path is explicit: hybrid now, "eventually it's going to be 100% consumption."
  • The horizontal bet: companies will buy vertical AI tools for SDR, support, legal — but "there's big room for horizontal plays." Monday wants to be "the default place for people to build agents and to collaborate between agents and people": agents output tables, docs, files; humans review and build their own. "If you haven't built an agent on Monday, you're not using the product properly… The boards and dashboards are going to be more in the background, the agents more in the forefront." Scale of ambition: "We're at 0.001% done of where the world is going."
  • Why ChatGPT, Gemini, and Anthropic don't win this: they're personal tools, not thousand-person collaboration surfaces — "it's like claiming there's no need for SDR software because you bought Anthropic." Companies adopting AI "have no idea what they need to do. No idea" — they need guidance on what to automate and what headcount to replace, not an off-the-shelf license.
  • The context argument, his sharpest moat claim: "no matter how smart you are, if you don't have context you cannot perform your job — 90% of the context is not documented anywhere… it kind of floats in the air." A forward-leaning small team like Jason's can go full AI; the 95% of the economy that isn't software companies faces a multi-year transition of humans and agents working together.

8. Two vertical bets into an "open market" — and why incumbents are underrated

  • CRM and service are being rebuilt from scratch, 100% agentic. When Monday first entered those markets the competition was brutal; now "the playing field is leveled": "Service dominated by ServiceNow, CRM dominated by Salesforce is open market today. I believe in their ability to change, but they need to prove it."
  • On whether HubSpot or Salesforce adapts better, an honest non-answer: bigger is harder because "it's hard to move humans" — and playing offense inverts the usual logic, since SMB customers might adopt new technology before enterprises do. "I don't know, to be honest."
  • His meta-point on the whole discourse: "every day I go on Twitter… this company has a more robust system of record, this company has a moat — who cares? What are you arguing — who's going to change last?" The question is offense versus defense, and "I think investors underestimate incumbents' ability to change" — one public company visibly reaccelerating will flip the cycle.

9. The one measurable AI hit: Google's AI mode

  • The single channel actually damaged by AI: Google's AI answers cut sponsored-link clicks, accounting for "about 10% of our acquisition in terms of new ARR" — the most transactional, high-intent SMB deals. Budget was shifted to longer-sales-cycle channels; "we have 70 other channels… we didn't see any impact on other channels." From his perspective the damage is real but isolated.

10. Skin in the game, the $70 bottom, and cycle discipline

  • The morning after the stock hit $70 (having woken at 3 a.m. Monday and 2 a.m. Tuesday): ~$3.7B market cap, ~$1.5B cash, no debt → ~$2B enterprise value on over $1.3B ARR, "like 1.5 multiple." His reaction: "what the market is saying to me is the company is worth zero. Okay, fine. Now I need to build" — and a feeling of relief. "Screw it. I'm going to go all in… There's only upside to where we're at." Some days, though: "I feel like I was ran over by a truck, hit by a plane, and barbecued — and it's just 11:00 a.m."
  • Capital allocation: an $870M buyback over the next two-three years, already begun in Q4. Personally he's constrained by a 10b5-1 plan but has a floor price "much, much lower" than today's — he's selling nothing, and still holds "80-something percent" of his shares 14 years in. No take-private: with 27% free cash flow and gross retention at all-time highs, "we don't need to raise more money… nothing is more sticky than a SaaS product." M&A is constrained by the valuation inversion — "every startup with 5 million of ARR is now being valued at 2 billion."
  • The discipline came from the top of the last cycle: when the stock hit $400 post-IPO, investor Ken Fox (likely Stripes) told him, "Isn't it great that the stock is going up without the revenue going up?" — everything gained was sentiment. He didn't celebrate at 400, and at 70 he says he'll focus on business metrics rather than the cycle. And being public, he argues, is the advantage over private rivals: "I was kicked in the head so many times by now that — okay, I got the message. When you're private, you can try and ignore what's going on."
  • Quick-fire honesty: asked to pick "OpenAI at 500 or Anthropic at 380," he invokes 1998 — "it's like saying Yahoo and Netscape are going to suck all the value from the internet revolution, and we know nothing… we're probably missing 90% of the picture" — while allowing "Anthropic have a little bit more momentum right now." His changed mind: a year ago "I didn't understand the magnitude of the change." The criticism that stings: storytelling — "if people knew what I knew, they would be much more confident in Monday."
Harry Stebbings

Ready to go. Eran, it is so good to have you on the show, dude. I have been wanting to do this one for a while, so thank you so much for joining me.

Eran Zinman

Thanks for having me, Harry. It’s great to be here again.

Harry Stebbings

By the way, if anyone is listening, you should be watching, because Eran looks younger than he did last time. It’s extraordinary, the volume that your hair has today, dude. You’re like, “This is not how I expected the show to go.” Clearly, we are lacking incredible discipline in our research.

I wanted to start on communication, actually, because we see the stock price, respectfully, in the dumps, but the actual fundamentals may be different. What is the stock market not seeing that you think they should be seeing?

Eran Zinman

Yeah. First of all, I want to acknowledge that it’s a crazy period for all of us, especially us as founders going through this massive change in the market. It’s definitely not easy—I’ll give you that. It feels like a roller coaster almost every day. Some days are extremely difficult, but it’s definitely quite a journey.

Fundamentally, we need to distinguish between what happens in businesses, which is one thing, and the sentiment change that happened, I would say, in the last year and a half—more precisely, in the last 6 months—which, from my perspective, felt very aggressive and powerful. On one hand, if you look at the earnings calls and how businesses operate, everything is normal. Some companies have even exceeded expectations, and businesses are working great.

1. Threat #2: Will OpenAI and Anthropic Own the Application Layer

At the same time, sentiment has shifted drastically, like I’ve never seen before, at least from my perspective. The negativity now being attached to software companies is extraordinary; it seems like every day there’s a new doomsday scenario, a new tweet. There’s a lot of truth to that, and I understand a lot of things from the investor perspective, so I’m not dismissing it. But we definitely need to distinguish between the operation of businesses and the sentiment change that happened in the market.

2. Threats Monday Faces Today

Harry Stebbings

I think a realization that the public markets and a lot of people are having is, “Wow, if we see an agentic evolution in the way that we think it will happen and proliferate, then there are core systems, potentially like monday.com and Salesforce, which, bluntly, are never used again and just turn into databases that agents crawl on top of.” Why does monday.com not become a layer that gets abstracted away?

Eran Zinman

Yeah. First of all, I think there are like 5 doomsday scenarios I’m familiar with, so that’s one of them. I’ll just take you back a little bit in time. First of all, there was everything about people vibe coding their own apps. That was one of them. Another option for a doomsday scenario was that some players, like Anthropic, OpenAI, or Gemini, would capture all the value from enterprise software. I think that’s another scenario people are talking about.

The third one is maybe what you refer to as a platform becoming essentially a system of record, and then other companies capturing the entire value that those companies offer. I don’t mind going through each one of them if you want. I can address each one of them.

Harry Stebbings

I love the way I suggested one of them and you’re like, “Well, actually, here are 3 more.” I can come up with an additional 3 if you want.

Let’s start with the one that you mentioned at the beginning: vibe coding. It was a journalist—I can’t remember what American channel it was, CNN, CNBC, or one of the acronyms that America has—who vibe coded her own monday.com in a couple of hours or whatever. Why will people not vibe code their own monday.com?

Eran Zinman

Yeah. From my personal perspective, I was coming off a long day of work and was about to go to sleep. Suddenly, I got a lot of messages on my phone saying that we were broadcast live on CNBC, and that, out of all the software in the world, the journalist had picked monday.com to show that you can vibe code software.

Obviously, she could have picked any software on the planet. Initially, I said it was a compliment. monday.com is beautiful software, so I felt it was a compliment that she had done it with monday.com. At the same time, she could have done it with Salesforce or ServiceNow, or she could even create a search engine or a social network.

Going back to the vibe-coding theory in general, first of all, I have to say that vibe coding is amazing. I’ve been coding all my life, since I was a kid, and seeing this amazing technology become real is unbelievable. But I think there’s a big difference between vibe coding a user interface and building actual software that works across an organization, with all the depth and functionality built into it.

3. Threat #1: Vibe Coding: Will Companies Vibe Code Everything

I’ve been coding all my life, and I know how relatively easy it is to create an interface and how hard it is to build the software. I think there’s a big difference, and some people might get confused by that.

Harry Stebbings

I completely understand that on the enterprise end, but on the consumer and SMB end—for that journalist, for an investor in a fund—does it not just cannibalize your consumer and SMB business?

Eran Zinman

Yeah, look, I said each one of those theories has some truth to it, but I think the impact is marginal. I think it’s a very small impact, if any. Going back to the topic itself, I think people underestimate how hard it is to maintain software over time.

It’s very easy to create the first increment of software, but to change it and adapt it over time takes a lot of effort and dedication. At the end of the day, businesses have a core business operation they need to focus on. If you think about software today, it’s a very small expense for most companies, and having a dedicated person or a team vibe coding some apps is a huge cost.

At the end of the day, vibe coding is amazing technology, but I don’t think it’s going to disrupt software companies. I’ll give you another point of data that I think is relevant. You can see amazing VCs like yourself and other people in the industry, and amazing founders building companies.

If you could vibe code any company or any startup, no company would have value—not in history and not today. Still, people invest billions into new companies and new startups, and entrepreneurs build new startups. I’ve read amazing news about Ramp raising at $30 billion, and about Harvey and Legora, companies you’ve talked about. You can argue you can vibe code them as well, but—

Harry Stebbings

But you couldn’t, actually. When you look at a company like Legora or Harvey, they are trained on a huge amount of legal data, which they have gained in the last 2 years from doing what they do. You couldn’t vibe code with the same quality of output that you could if you vibe coded monday.com as a consumer.

Eran Zinman

No, actually, I don’t think so, because at the end of the day, it’s true that those companies accumulate data and information over time, but I can argue that you can probably get the vast majority of the value even without that specific training.

At the end of the day, you can argue that you can vibe code any company. As much as I think the technology is awesome, we have our own vibe-coding capability within the product. Of all the theories about how software is going to be disrupted, this is my least favorite one.

I don’t think it’s going to happen, and I think most investors that I speak with, as well as people within the industry, don’t think that’s what’s actually behind what’s impacting stocks and software companies today. Again, it can have a marginal impact, but I don’t think that’s the majority of what we’ve seen in the market.

Harry Stebbings

I completely agree with you on enterprise. The idea that enterprises will do that is wonderful. Sadly, enterprises don’t work like that; otherwise, I would be much richer if their buying decisions were so much quicker.

The second one you mentioned was that we’re going to see OpenAI, Anthropic, and Gemini—the model companies—move into the application layer. We’ve seen Anthropic do Cowork. We’ve seen Anthropic do legal. Dario, he just killed my CrowdStrike over the weekend. Thanks, Dario. Cheers.

Why are they not going to move into the application layer so much more aggressively?

Eran Zinman

Yeah. Again, I think there’s obviously some truth to that, and they might capture some of the value, but I think people overestimate how much they’re going to capture.

I want to take you back in history. I'm old enough to remember when Amazon built AWS, and everybody back then said that Amazon was going to capture all the enterprise software value because, before that, the hardest part about building a company was getting the servers up and running, the website working, storage, and 24/7 availability. That was the hard part. That was the heavy lifting. I remember how people got excited when they got a website online.

When AWS came out and it became so easy to build a website, everybody said Amazon was going to capture all the enterprise value because it was so close to the value they offered. What really happened was the exact opposite: we saw a boom of companies building on top of Amazon, and software grew exponentially.

At the end of the day, I'm not saying Anthropic or OpenAI aren't capable of building enterprise software. I'm saying the opportunity they have as the infrastructure of the LLMs of the future is so massive, and going after enterprise offerings is a whole different business to build. When you sell to companies, it's a different sales process and a different mechanism. Nobody's going to buy software for the entire organization based purely on a PLG play. The way they're going to adopt it is that they want to be handheld, especially if you want to use software across the organization.

I'm not saying people won't use Anthropic and OpenAI. For sure they will, but I don't think they're going to capture all the enterprise value because they have a much bigger opportunity ahead of them, and it's not their focus. No company on Earth, with AI or without it, can do everything. I don't believe in one player being the one software to run everything in the organization or at all. So I don't see this playing out.

4. Threat #3: Will Agents Turn Monday and Salesforce into a Database

Harry Stebbings

I think that's probably the weakest one. I totally agree with you. When you look at OpenAI—or sorry, Anthropic—moving into security, it's a very weak argument to suggest that replaces CrowdStrike or Palo Alto Networks. I completely align with you on that, actually.

The third one is a tough one, I think, which is how you embrace an agentic future, and whether it makes you a database and not an interaction platform as well. How do you take that one?

Eran Zinman

It's a tough one because it's true. That's why it's tough—because it's true. I believe that with all my heart.

Basically, the way I look at it is that, if you think about it very broadly, software as we know it hasn't changed for 25 years. Even before the web, I was building software for DOS, without an interface. It was the same thing: you would build a database, and you would create dashboards and analytics on top of it. You might have some automations and workflows, but essentially, the value was the same from day one.

It's true that interfaces changed. People initially built for desktop applications on Windows, and then it moved to the cloud, so there was a major benefit because it became real-time and everybody was seeing the same thing at the same time. Mobile came into our lives, but if you judge by value, it was basically the same for 25 years.

If you think about it, it doesn't matter if you built CRM software, IT software, or work management software: 90% of the work was done outside of the tool. If you're a salesperson, you would make the call outside of the CRM, build the deck outside the CRM, and prepare for the call outside the CRM. Eventually, yes, you would track the data in a CRM, and your VP of sales would be able to see what's going on.

The same goes for IT. The same goes for monday.com. You would track your workflows and projects, and you would do everything within monday.com, but the work itself was done outside of the tool.

If you think about it, software was extremely beneficial. I can't imagine the world before software because we take so many things for granted: everything is centralized, real-time, in one place, and everything is tracked. We might take it for granted, but it was a major step.

Going back to your question, AI changed everything because now, with AI, I think we flipped the equation. I think AI can potentially do 70–80% of the work, and not 10–20% like it used to before AI was brought into our lives. I think that changes everything in terms of what companies need to do for their customers and what customers expect from software. It will only grow over time. Nobody will want to buy software that isn't doing the majority of the work for them, because otherwise you're just buying legacy software.

Harry Stebbings

If that's true, and it does become a database, where is there value in that?

Eran Zinman

Well, I think this is where, in my opinion, investors in the public market get it wrong. If you judge by what software is doing today, you're right: if we don't change, eventually we'll become a database, and nobody will buy monday.com to track their work because they'll buy software from other vendors that fulfills that promise. But that's not the way it's going to play out.

5. Quickfire: Marriage, Biggest Short, Mentors

I can talk about it specifically if you want, but we're changing everything, basically. Going back to what I've said, I totally understand the way some investors or the public market reacted. I think what the public market is saying, essentially, is, “We understand that the value is changing and software will be different going forward, but we don't know who will be able to change.”

I get it, because change is extremely hard, especially for an existing company. The public market is saying, “We don't know which company will be able to change. There are so many parameters to that, and we're out until we get that confidence.”

6. Why is Monday Adding 15% Headcount When Everyone is Cutting?

If I take a step back, I think that the TAM of software, and how much companies are going to spend on software going forward, is going to be 100x what it is today. Software will be much more valuable going forward. Software TAM is going to grow exponentially, and if you combine this with the fact that companies are going to change and capture this value, I think the opportunity in the software market today is like we've never seen before in our lives.

Harry Stebbings

We see enterprise spend on technology at 8–12%. It's a varying range across a number of different verticals and variables. What do you think that will be in 2030? I know it's a hard question, but give me a guesstimate.

Eran Zinman

I can give you an example from monday.com. I've actually done this; I've checked it myself. I think a company like monday.com—let's say we have $1 billion in expenses—a company like monday.com will probably spend 60–70% of the budget on headcount and then 7–8% on software.

But if we can flip the equation and scale businesses without relying on headcount going forward, every CEO will gladly increase spending on software because it's going to be marginal compared to the headcount growth that you plan for your business going forward. I think this will play out more and more into the future.

As AI becomes more dominant, companies will spend much more on software and much less on headcount going forward because they'll just become more efficient, and they'll gladly spend on that software.

Harry Stebbings

Can I ask you, though? Your analyst day presentation showed 20% year-on-year headcount growth in 2026.

Is that not completely paradoxical to what you just said about more spend on technology, agentic usage, and organizational efficiency when we're increasing headcount by 20%?

Eran Zinman

Yeah, no, I agree. I think we need to differentiate between the transition and where we're going. For us, we actually brought it down a little bit. In the last earnings call, we said it's going to be mid-teens, and I think there's also potential that we might even take it lower. I don't know; we'll see.

But I don't want to press the brakes violently. I think we need to do this responsibly because there's a transition period. But if you look at the horizon, 2–3 years—

Harry Stebbings

Can I push you? Why not? I mean it in a nice way, dude. The stock's in the dumps. I just had Seb from Klarna on. We said we'd be honest: you're Israeli, I'm British and old, so fuck it. Yeah, it's fine.

I just had Seb on from Klarna. I mean, dude, he's in the dumps too. Poor guy. I love Seb. But he's like, “We were at 7,000; we're now at 3,000. By 2030, we're going to be at 2,000.” I mean, I think in a couple of years there'll only be Seb at Klarna.

Why are we not being more aggressive? Fuck it, now's the time.

Eran Zinman

Look, first of all, these are discussions we have in the leadership team, and maybe we'll make other decisions, but I don't think that's the point. I don't think that if we reduce headcount dramatically, it will change investor perception about monday.com. I just don't think that's the essence of what we're seeing in the market.

Going back to what I've said, I think investors don't know which company is going to change. We just had the earnings call 2 weeks ago. A lot of fun—obviously, I'm being sarcastic.

Going back to investors, I've talked with all of our major investors, and everybody's saying the same thing. Eventually, what they want to see is business revenue accelerate. I totally get it, because I think what people are saying is, “There's huge demand for AI products, and people want to buy AI. We're going to have a few years now that companies are going to look for AI solutions.”

Given that we're going to see infinite demand for AI products, there shouldn't be a demand problem. So you need to show us or prove to us that you can supply that demand to your customers and new customers.

And because of that, we want to see acceleration of revenue going forward. They’re right. I think that’s the best way to prove it, because if there’s infinite demand and you’re able to capture that, there’s no reason for your business not to accelerate.

I think that’s our role. This is exactly what we need to do and prove to ourselves and to our investors going forward: that we’re able to accelerate the business and capture the AI demand that exists now in the market. This is Roy’s and my responsibility going forward.

Harry Stebbings

I get you, but everyone is cutting headcount. To still increase it by the mid-teens is still a lot. Is it just that you need the people? I still don’t understand.

Eran Zinman

Yeah. The way I look at this is that I’m not arguing that companies need to become more efficient, so I’m not dismissing it, and we will become more efficient. I’ll give you some examples of things we’re already doing.

First of all, we had a team of about 100 SDRs, and we’re now doing it with agents. 100% is being done with agents. We moved those SDRs to do outbound. All of our support is being done with AI, and all of our developers are using Claude Code and Cursor.

7. How Monday is Using AI to be More Efficient

I don’t think there’s any company that’s pushing AI efficiency more than we do. We want to be at the forefront of that, and we’re pushing that on all cylinders. We are becoming more efficient.

Harry Stebbings

I just want to drill down on that because that’s super interesting for me, nerdily. When we look at the sales team’s utilization of AI, when you say, “We’ve replaced SDRs,” but then you said they’re moving to outbound, how are you using AI specifically in the sales team to make the sales team more efficient?

Eran Zinman

Basically, a customer today goes into monday.com when they leave their details on the website. Let’s say they leave a contact-sales form. The way we used to do it before AI was that we had a team that would call back those customers, try to figure out how to qualify them, check the opportunity, and basically qualify them and help them schedule a meeting with the AE—the account executive—on our team.

This is all done by AI today. I’ll give you some stats. It used to take, on average, 24 hours to get back to a customer. Now it takes 3 minutes. We used to miss a lot of the calls; people would not answer the calls.

Now everything went up. The conversion rate went up, the number of people answering the call went up, and the opportunity-to-book rate went up. All parameters went up. AI speaks all languages and is available 24/7, so it’s been quite an amazing transition.

Harry Stebbings

Love that. Fascinating. You said support was also impacted. I’m really intrigued. Do you use an external provider for customer support, or have you built your own? I interviewed Ariel Cohen from Navan and Jack Zhang from Airwallex, and they built their own. How did you think about that?

Eran Zinman

When it comes to the SDR part, we’ve done it on our own. We built our own solution. For support, we use some third party, but a lot we do ourselves as well.

I think you still need to highly customize tools today in order to properly use them, and things are moving so fast that we just felt building our own was probably the right path to take at this point.

Harry Stebbings

Have you seen a shift in the engineering team from building with Cursor to Claude Code?

Eran Zinman

I’ve seen some of it. I think right now it’s a sense of flavor, but essentially, we’re in a transition period, and we definitely see an increase in output for engineers, by the way.

I think part of it is that you find new bottlenecks that are not attached to writing code. On the one hand, we see an increase in personal productivity, but again, there are new bottlenecks you find each time you increase one of those productivities. Basically, we’re on a journey to increase more and more the output of our R&D team.

Harry Stebbings

So, Seb from Klarna said 3,000 today and they would be 2,000 by 2030. How many do you have today, and how many people do you think you’ll have in 2030?

Eran Zinman

Today we have about 3,000 people.

Harry Stebbings

2030. Wow.

Eran Zinman

My gut feeling is probably not going to grow substantially. But look, I think efficiency is important, but what’s even more important is the opportunity that we have.

I think this is where people are missing the point, from my perspective, because it’s true that we can focus 100% on efficiency and reduce headcount and expenses. But going back to my point, this is the biggest opportunity in software ever in our lifetime—the biggest opportunity that we’ve ever had as a company and as an industry.

It’s the beginning of the most amazing journey for all of us. So what I want to do is capture as much as I can out of this opportunity, because it’s out there and we can do it. I think this is where people are getting it wrong.

Harry Stebbings

On the one hand, I see people excited about private companies because they build tools in the AI era that capture what I’ve referred to as “doing the work.” But I’ll tell you a secret: public companies will do it as well. We’re going to do it; we’re already doing that.

The challenge I have is with bolt-on AI strategies, which I’m not delineating between public or private. I’m delineating between scale companies and non-scale companies, or AI-native companies. I think the bolt-on AI strategy—sorry, I’m being blunt—could be a UiPath, it could be an Airtable, it could be, you name it, that ilk-era company, versus an AI-native company built from the ground up with AI.

It’s just very different in how you build, integrate, adopt, or approach AI as a fundamental platform.

Eran Zinman

No, 100%. We were the victims of this as well. Going back, I’ll share a little bit of our journey.

Going back a year and a half ago, or even 2 years ago, when Sam Altman wrote that famous tweet, “This is ChatGPT; you can play with it,” I remember that. I’ll give you the kind of relationship that we had with AI.

Initially, I was excited. I’m excited about every new technology. I’m also a person who likes to try things with my own hands, and we played with it, and it was amazing. But we didn’t get it, to be honest. I think most of us didn’t get it. Maybe some of us got it.

Initially, the investors didn’t know what it meant either, and we heard from investors, “It’s cool, there’s hype around it, but we don’t know.”

Something changed about a year ago. I don’t know what it was, to be honest. It’s not like there was 1 tweet that I saw or 1 product. I feel it was a combination of many, many data points, but I think it was a collective understanding that things are changing and changing forever.

This is where you started to see the change in market sentiment, and I felt like there was a lightbulb moment at that point. Before that, we had done a lot of things; it’s not that we didn’t do things, but we built some AI features.

But as you said, I call it that we sprinkled some AI dust on top of our product. Essentially, we didn’t know what to build. We built a way for people to build formulas using AI. We built AI Blocks and AI Columns, but essentially it was sugarcoating our product because the value hadn’t changed. The value was the same.

8. What Happens to Seat Pricing? What Comes Next?

Harry Stebbings

How do we solve the problem of seats, Eran? We’ve lived—and I’m showing my age, obviously—in a seat-based SaaS economy where we sell seats, and that’s fantastic when headcount scales, as it always has done, and people renew.

But in a world where headcount is reducing, where efficiency is increasing, and we’re moving away from seats, what do we do when our core pricing dynamic goes away?

Eran Zinman

Yeah. Going back to the transition, like I said, initially it was the AI dust that we sprinkled on the product. But then we realized that the value we need to give to our customers—not just us, but every software company—is completely different.

What we’ve done internally is rethink what we’re doing as a company: what’s the value we’re trying to provide to our customers with the monday work management platform, and also with CRM and Service, and rethink our whole product.

Part of it is pricing, like you said; that’s going to change dramatically. Our go-to-market is going to change, our homepage is going to change, and the ads are going to change.

And the most important part—what our product is giving, the value it gives to our customers—is now going through the biggest transformation since we launched the company back in 2013. It’s the biggest moment for us in the history of the company.

Harry Stebbings

Can I push you on the pricing? You said it’s going to change. What does it change to?

Eran Zinman

Well, eventually, I think it’s going to be more consumption-based, and then entirely consumption-based going forward. I think this will also be a transition, but now it’s going to be hybrid, and eventually it’s going to be 100% consumption.

Harry Stebbings

Got you, totally. How do you feel navigating that transition?

Eran Zinman

First of all, maybe I’ll just explain the transition that we’re doing, just to make it more concrete. Basically, companies want to adopt AI, and they’re going to adopt vertical tools to do that.

Like the SDR example I gave you—maybe another example for support; for legal, there are a lot of vertical solutions people are going to adopt. But I think there’s a big room for horizontal plays, and this is exactly what we’re going to do with monday.

Basically, we want to be a place that orchestrates between agents and humans, because at the end of the day, maybe in the far future, agents will do 100% of the work. I don’t think it’s going to happen, but maybe it will happen to some extent.

We’re going to have a huge transition period where humans and agents need to work together, and we want to make monday the default place for people to build agents and collaborate between agents and people.

Harry Stebbings

So essentially, you'll build Monday, you build agents on top of Monday, those agents will output tables, docs, and files, people will go over it, they build their own agents, and essentially you want to become the default place to do horizontal agents across the company. Do you think you're the best place to do that, though? Everyone wants to do that, and Anthropic wants to do that. ChatGPT wants to do that, too. Going back to that one, actually, they do want to do that, and that's right in their wheelhouse. Why are we the best place to do it?

9. What No One Sees About Enterprise AI Adoption

Eran Zinman

So first of all, I don't think that ChatGPT, Gemini, or Anthropic are going to do it, because, going back to the second theory that we discussed, of course people are buying Anthropic's Claude, they're buying ChatGPT, but it's not a tool where you work with another 1,000 people and share information. It's a personal tool that people use. There's a big difference between selling a tool that can be used personally and building a tool for people to collaborate with agents. It's a very different product.

Harry Stebbings

If you look at OpenClaw and what Peter Steinberger's done and what he's doing joining the team at OpenAI, and then you look at their movement into enterprise and Anthropic's focus on enterprise, again, critics would push back and say that's just not true.

Eran Zinman

Yeah. I'll explain again. I think a company today that wants to adopt AI has no idea what they need to do. No idea. It's a new technology. I think we live in an echo chamber of tech, but the world out there is very different, and I think essentially companies will want to buy AI. They will do whatever they need in order to buy AI capabilities because it's going to be a competitive market, and if they won't do it, they won't survive.

Harry Stebbings

Do you not think that's where ChatGPT's brand wins? Fundamentally, the brand of ChatGPT is so strong that they are signing enterprise contracts with a velocity we haven't seen before because of that brand. Anthropic are too, but again, I go back: as a Monday holder, do we not need to jack the shit out of our enterprise brand? Because otherwise they're going to eat the momentum on the enterprise side.

Eran Zinman

So I think we need to differentiate what an enterprise contract means. Okay? The fact that ChatGPT or Gemini or Anthropic are selling a contract that 1,000 people, let's say, within Monday can use Anthropic—it's great. But that's not the product I'm talking about. That's like comparing Microsoft Office with Monday. It's not the same thing.

There are tools that people use individually, which is great: personal productivity tools and building agents. But then there's the actual work. It's like claiming that there's no need for SDR software because you bought Anthropic. It's a different problem to solve. So I think solving how people and agents are working together in one workspace is a very different product; it's a very different problem.

I think companies will want guidance on how to do that. They're going to need help setting up agents, figuring out what they can automate with agents and what they can replace in terms of headcount. And this isn't solved by buying an off-the-shelf, generic product. You will need a product that can help you collaborate between humans and agents. It's a very different product compared to just buying a license to an LLM.

And I think eventually, if you look at Anthropic, OpenAI, and Gemini, they have a much bigger opportunity they want to chase. They want to be the backbone of the LLM industry. They want to capture as much as they can in terms of that market share, and I get it—it's a huge opportunity. Again, going back to my AWS comparison, they are the infrastructure, but there's going to be a lot of products built on top of that.

I think, if anything, we're going to see an excess of software being built on top of the LLM, not less—exponentially more—because the opportunity is so massive and the TAM is so huge. Going back to Monday, we're going all in for that. We're changing the product, the value proposition, how people use the product, how people onboard, and what people should expect from the product. If you haven't built an agent on Monday, you're not using the product properly. That's a major shift.

The boards and the dashboards are going to be more in the background, and the agents more in the forefront. It's a huge change, a scary change, but I believe in that with all my heart because I think the opportunity is massive. We're 0.001% of the way to where the world is going.

Harry Stebbings

Do you think we overestimate the speed of adoption for enterprise AI usage, or do you think we're actually at a tipping point and it will tip much faster than we think?

Eran Zinman

I think technology is moving fast. I think organizations are going to take more time. What is AI adoption? There's so much nuance to that. There are so many things. Look, at the end of the day, I think what people are confusing is that AI can get super smart, and we've seen it growing exponentially, but no matter how smart you are, if you don't have context, you cannot perform your job.

Even the most intelligent person on Earth cannot do their job if they are not aware of the context. If you think about any company, even Monday itself, 90% of the context is not documented anywhere. Nobody knows it. It's something that floats in the air. What's the idea? What's the strategy? Who's doing what? What's next month, what's next year, how are we going to do it, why are we doing what we're doing, and what's the thought process behind it?

So I think we're going to see a transition period before all that information, knowledge, and intelligence is going to be documented, which might happen in the future. I think we have a huge transition period of people working with agents. I think you can see some small companies, and I've been following Jason Lemkin and what he's doing on his own team. I'm a big fan of Jason.

Harry Stebbings

You know, the joke I say with Jason is that the best venture fund of the last decade was Jason Lemkin's unresponded-to inbox, because every great founder sent him an email being like, “Please invest,” and he just didn't get back to them. I always joke with Jason that we have a one-sided relationship where I listen to every word he says and he's my mentor, but he's not aware of it. I do a show with him every week, and he is my mentor, and he is aware of it. But he is so ready; he is so into it. It's insane.

Eran Zinman

I know. But look, at the end of the day, I think a small team like Jason's team—and Jason is very forward-leaning—can replace everything they do with AI. But for an existing company in business, it's going to be more of a transition over many years, and we need to remember that most of the economy—95% of the economy—is not software companies; it's actual businesses.

So, going back to my point, we're going to see a transition period of companies adopting AI, AI working with humans, and humans collaborating with agents. It's a massive opportunity, and I don't think OpenAI, Anthropic, or Gemini are going to go for that because it's such a different sales process: enterprise sales, top-down, and different tool use.

We're going to go all in for that opportunity because our advantage is that we are the best platform for people to work together across the organization. So we're going to take that part of the business, add the agents on top of it, and change the value and what people do with the product. I believe it's going to be massive going forward.

10. How Google AI Overview Smashed 10% of our Customer Acquisition

Harry Stebbings

If we shift a little from enterprise down to—it can still be enterprise—but more SMB and consumer, one thing that Monday has done unbelievably well, and we spoke about it last time, was the customer acquisition machine you've built on SEO, content, and YouTube. It's been phenomenally successful. How do you think about critics who say that customer acquisition engine is completely changing in a world of GEO or LLM discovery, in a changing content world? How do customer acquisition channels and funnels change?

Eran Zinman

Yeah. So, going back to my original opening where I said that there's a sentiment change but businesses are unaffected, we were affected by one thing, which is Google introducing AI Mode in the search results. Google used to be a significant acquisition channel for us, and definitely it took a hit in terms of people clicking on sponsored links because people see the AI answers.

Harry Stebbings

When you said it took a hit—when you said it took a hit, how much of a hit? I'm sorry, I'm really naive here. 10%, 30%, 50%? Broad strokes.

Eran Zinman

It was about 10% of our acquisition in terms of new ARR. But again, Google is very transactional, so people usually, when they're searching for something, are willing to buy at this point because the intent is very high.

So we lost some of the more transactional deals, more SMB-oriented, and we shifted that budget to other channels, but those have a longer sales cycle, so we definitely took a hit because of that. But apart from that, we have 70 other channels that we acquire customers from, and we didn't see any impact on other channels. So it was a significant impact, but from my perspective, it's isolated to that.

Harry Stebbings

Can I ask a hard one? If we are the work platform between agents and humans and we have this grand future—it's the most exciting time ever—why have you not bought any of your own shares back?

Eran Zinman

Well, we announced a buyback program of $870 million, and we said we're going to spend it over the next 2–3 years. We've already done some buyback in Q4, and we said that if we're going to see opportunities, we're going to buy back our shares. Definitely, there are opportunities right now, so we're looking into that, and we do have a buyback program.

Harry Stebbings

What about you personally, dude? We saw the ServiceNow CEO spend $3 million, and that was revealed to be less than his car collection, which was a rather annoying title for an article. I saw it and I felt sorry for him. I was also really intrigued to see the cars, which they didn't show. Why not buy it back personally?

Eran Zinman

Yeah. So, first of all, I'm on a 10b5-1 program. Basically, I have to make a 6-month plan 6 months in advance. I'm not saying I won't—when the plans open up, I might buy more shares personally again. It's something I need to decide with my wife; it's not a personal decision for me. But definitely, it's an opportunity.

I can share another thing: neither myself nor my partner Roy nor the rest of the leadership team is selling shares. In my 10b5-1, I have a number I'm not willing to go below in terms of selling shares, and I can say the price now is much, much lower than that number. So, I'm not selling any shares personally.

Maybe I'll share another thing because it's public information. Since the IPO, I still hold—again, I don't know the exact number, but probably 80-something percent of my shares. So, I sold less than 20%. Fourteen years into this journey, I don't think I need to prove more that I have all my skin in the game. I'm 100% in. I believe in the future of the company, and I think, as I said, it's one of the biggest opportunities that we've ever had as a company.

11. How to Manage Internal Morale When Stock is Down 60

Harry Stebbings

Can I ask you, from a personal perspective or a leadership perspective, when you have a challenging period like this, what do you know now about how to galvanize a team when a stock price is so impacted? Of course, people look at it every day and look at their net worths.

Eran Zinman

Yeah. Look, it's been a roller coaster. It's been hard emotionally, everything in the last few months. I can share that—it's still fresh—but the last earnings call, the stock went down to $70. Obviously, when the stock is going down, and I've seen all the earnings calls before Monday and after Monday, I felt like no matter what companies were going to announce, the stock was going to go down 20%. I wasn't optimistic. I wasn't sure what was priced in and what wasn't, but it is what it is. I get it. The sentiment is so negative.

Harry Stebbings

How do you feel going in when you know that you're going to get pummeled? Are you like, “Fuck it. You know what? There's nothing I can do”? Are you like, “Oh God, I'm dreading this. Oh no”?

Eran Zinman

Yeah. Look, I didn't know what to expect. Overall, I'm trying not to use the stock price to manage my decision-making process, but I look at it. You cannot ignore it; it has a psychological impact, for sure. It's definitely not easy or fun when you go up and talk with analysts and investors and nobody's happy.

Again, I don't think we're unique because ServiceNow is down 50% and Salesforce is down 60%. It's not helpful, so I understand there are things I can control and things I cannot control. I cannot control the negative sentiment in the market. What I can control is what we can do about it, so I'm trying to focus on the things I can control.

Going back to the earnings call on Monday, the stock went down. I obviously lost some sleep over it. I woke up at 3:00 a.m. thinking about it. Tuesday, I woke up at 2:00 a.m. and didn't fall back asleep. But when I woke up Wednesday and the stock was at $70, I had a feeling of relief, to be honest, because I said, “Okay, $70 represents, let's say, a $3.7 billion market cap.”

We had—I don't remember the exact number, but roughly, let's say—$1.5 billion in the bank, cash, no debt. So, the enterprise value is $2 billion. We have, again, I don't want to disclose a specific number, let's say, over $1.3 billion of ARR. So, it's like a 1.5x multiple.

I felt like, okay, what the market is saying to me is—again, air quotes—“The company is worth zero.” Okay, fine. Now I need to build, I need to prove. Suddenly, I felt relieved because I'll do everything needed in order to make the company successful. It can't get any worse. The stock can go down, but I feel this is the lowest sentiment software companies have ever had. It can get lower, but to be honest, it's pretty low right now.

Harry Stebbings

I love you. We get on well. My friend, the French analyst, goes, you know, because I obviously am a monday.com holder. He's like, “Dude, the thing about Monday, I thought there was a flaw. I was wrong.”

Eran Zinman

Yeah. Look, I'm not saying it cannot go down. Obviously, every day there's a new tweet and the stock is going down 7%. I cannot control it. But what I feel now is, you know what? Screw it. I'm going to go all in. I'm going to go all in—both Roy, myself, and the management team. This is the biggest opportunity. There's only upside to where we're at. We're going to take the risks, we're going to go all in, and we're going to do whatever is necessary to win. I'm extremely motivated for that.

12. Do Private Companies Have Advantages Public Companies Do Not Have

Harry Stebbings

Do you think private competitors have an advantage over you that you don't have because you're public? If you look at Stripe and Adyen, I think Stripe has an inherent advantage in being private that Adyen doesn't have because it's public—in what they can do, how aggressive they can be, how they approach product, you name it. Do you think that's the case here?

Eran Zinman

I think the opposite.

Harry Stebbings

The opposite.

Eran Zinman

Because if you relate to what I've said, I feel like I was kicked in the head so many times by now that, okay, I get it. And I feel when you're private, you can try and ignore what's going on and even say, “Everything is okay.” But for me, I get it, and I don't blame the investors. I think investors are super sophisticated and it's an amazing market. I think what the investors are saying—I got the message. I got the message. And they're right.

They don't know who's going to be successful. But I think this is where they get it wrong, because I feel—basically, I think what I'm trying to say, Harry, throughout our conversation is: are you playing defense, or are you playing offense?

Every day I go on Twitter and read what people are saying, and everybody is publishing an article: This company has more robust systems of record, this company has a moat, this company is enterprise. Who cares? Who cares? What are you arguing? Who's going to change last? Who has more time? I'm saying the opposite: everybody has to change. Everybody has to change. The faster you change, the better.

Some companies will not be able to change because, I don't know, the founders are not there, because it's hard, because the DNA is not there, because it's a 100,000-person company, because they're not sure where they're going, because they don't have a culture of execution.

My confidence comes from the culture we built, the fact that we've always been great at execution, and the fact that once we make a decision, we're going to go all in. We have everything needed. We have the cash, we have the talent, we have the execution, and we know what we need to build. That gives me a lot of confidence: the people in the company and our mission.

So, I think if you're playing defense, good for you. I feel for us it's an opportunity to play offense and do whatever we need in order to win. And this gives me a lot of confidence because I'm building the future.

Harry Stebbings

Can I ask you, you said that you have $1.5 billion and it's $3.7 billion or whatever it was. There comes a time when actually it's just too low. It's mispriced. At that point, I have many public-market friends now who are going, “Fuck this. I want to take it private. This makes no sense anymore. It is strategically wrong.” Would you like to take it private?

Eran Zinman

No, I don't see a reason. Look, I think at the end of the day, you can be private, you can be public. The question is: do you need to raise more money? And we don't. We generate 27% free cash flow. We don't need to raise more money. We have everything we need going forward. If anything, we'll become more efficient.

13. With $1.5BN in Cash, Why is Eran Not Buying More Companies…

I see the retention rate is the highest ever. Gross retention is the highest ever. We're still acquiring a lot of customers. So, I'm very confident about the business, and I think this is where people don't understand that the business is working well. Things might change, but nothing is more sticky than a SaaS product. So, I'm definitely not worried operationally, and we are changing as we speak. We don't need to raise more money, so there's no reason to go private. We can stay public.

Harry Stebbings

You said about $1.5 billion in cash. What a wonderful luxury that is, also, that not many have. What would you like to buy that you haven't bought from an M&A perspective? Why are we not being more aggressive?

Eran Zinman

Yeah. So, look, we're looking into companies, and we also met a few that we were close to acquiring. But at the end of the day, this is not how we're going to win. If I need to bet the whole company's future on an acquisition of a startup, I'm not doing my job as a CEO.

Look, the problem now with private companies is that we have the opposite valuations between private and public. If monday.com is valued at $3.7 billion, every startup in the private market with $5 million of ARR is now being valued at $2 billion. I can buy it partially with cash, but I'll need to use my stock as well. So, I don't have a lot of opportunity to buy a few billion dollars' worth of a private company. It's not going to play out. And again, I feel we have everything we need in order to execute.

So I think it’s a cycle. It’s a cycle for public companies, and it’s also going to be a cycle for private companies. There’s a lot of money in private companies and from private investors, but it’s a cycle. At some point, investors are going to see the same company 20 times a month, and LPs are not going to pour in a lot of money. I get it. I’ve been in cycles before.

Harry Stebbings

Are you in CEO groups, WhatsApp groups?

Eran Zinman

Not a WhatsApp group, but I have a few CEOs I consult with.

Harry Stebbings

Yeah. What do they say? Are you guys all just going, “What the fuck are we doing?” together?

Eran Zinman

Not really. The problem with other CEOs is that people don’t expose their emotions too much, I’ll say that. But I think people feel resilient. I think we give each other confidence. Some CEOs are—I wouldn’t say ignoring the problem, but they don’t understand the magnitude of what needs to change. I think some are more advanced in how they think about it and understand the magnitude of what needs to be changed.

Again, my confidence is coming from doing and changing. That gives me a lot of confidence going forward. I don’t need anybody to pat my back. I’ve got Roy, my partner, and the rest of the leadership team, and we feel very confident about where we’re going.

Harry Stebbings

Can I ask you personally, from a marriage and personal perspective? It’s hard, what you’re going through, and I don’t think a lot of people quite realize the emotional and personal toll that it takes. Getting on a show like this with me, even after everything that you go through, is intense.

I remember Seb from Klarna saying he does shows and interviews, and he did one that was so fucking hard. They just shit on him, shit on him, shit on him. He got in his car, played “Under Pressure” by Queen, and just sang at full pitch. He always thinks of that moment. From a personal perspective, what are the things that get you through the really hard times?

Eran Zinman

First of all, I want to acknowledge that it’s hard. I told somebody the other day that some days I feel like I was run over by a truck, hit by a plane, and barbecued, and it’s just 11:00 a.m. So definitely, there are days like that.

But I must say that I feel very good now, and I feel we’re doing the right things. I’ll give you two things that really help me. One is the people in the company. That’s something very significant to me because once we tell them what we’re doing and focus on execution, I can see in their eyes that although it’s scary—we’re changing a lot of things and taking big bets—they’re excited. I can tell in their eyes that they appreciate that we don’t ignore the problems or say everything is okay. We are changing and adapting for the future.

People are working incredibly hard. They’re dedicated from the bottom of their hearts, and that gives me a lot of confidence. The second thing, and I don’t want to get too emotional, is my family—my wife and my kids. They’re super significant.

Harry Stebbings

Yeah. I remember when I had a hard time fundraising years ago. I remember crying in the middle of Leicester Square on the phone to my mother, and I was expecting this loving response from my mother. She’s very sweet, and she goes, “Harry, I did not give birth to a fucking loser.”

I was like, “Oh, shit.” She said, “You know what? Wake up tomorrow. Tomorrow is another day. You’ve got this.”

Whatever it is, there is something about your family in that moment that just gets you through it. I totally get that.

Eran Zinman

Yeah, and also my extended family—my parents, my sisters. I feel I have a network of support.

At the end of the day, what I really care about—you ask me about my personal wealth—I don’t care. I don’t care. I just want the company to be successful. I feel an immense sense of responsibility for the future of the company, for the employees, for the investors, for everybody who’s part of that ride. I want to do whatever it takes to capture this opportunity, and I want to play offense.

I think that’s the point. At the end of the day, as I said, I think there’s so much noise, and just listening to the noise is the wrong thing to do as a leader and as a CEO. The noise is Twitter, other articles, even the public markets.

Harry Stebbings

There’s a content creator, influencer—whatever. I’m quite into these kinds of inspirational speakers—Alex Hormozi. He says, “Whenever I’m going through a hard time, I think the harder the challenge, the greater the story that comes out of it.” This is the story that you will one day tell your kids.

Eran Zinman

Yeah. I’ll tell you how I look at it: I got a front seat in probably one of the most exciting periods in human history—the birth of intelligence—and I can navigate this ship. It’s amazing. It’s such a great opportunity.

Everything in life is: is it a glass half-full or half-empty? I can look at it and say, “I was on a path and everything was great, and we built this great company.” But the way I look at this today is that maybe this is our biggest opportunity as a company. Maybe we waited for that moment, and if we do the right things, we can reaccelerate the company and even grow much larger than what we could have become as a company. I hold on to that, and that gives me a lot of confidence.

If you ask me today how I feel, I feel great because, as I told you, we hit the bottom—or maybe we’re close to the bottom—and from here we can only grow and focus on execution. This is exactly what we do.

14. What is the Most Offensive Bet Eran Would Like to Take?

Harry Stebbings

You said that this is a time for offense. Before we do a quick fire, if I were to ask you, what’s your most batshit-crazy offensive move that I’m sure is totally unrealistic but you would like to do?

For me, I look at it as a load of companies like you, Duolingo, and a load of others where I’m like: crazy mispriced assets, clearly brilliant companies. Let’s roll them up and buy them in a really aggressive way. I want to raise $100 billion and do this. It’s a batshit-crazy offensive idea. What would you say is yours?

Eran Zinman

Our strategy is twofold. One, in terms of our horizontal platform, we’re going all in on agents and humans working together. We’re shifting the product 100%—the pricing, the go-to-market, the product.

We have 2 vertical offerings, CRM and service. For those, we’re building the products from scratch and making them 100% agentic. We’re going all in on that opportunity.

The way I look at this today, service is dominated by ServiceNow and CRM is dominated by Salesforce, but it’s an open market today. I believe in their ability to change, but they need to prove it. I want to go all in. We made the choice to go for CRM and service back in the days when we had crazy competition. Now I feel the playing field is level, and there’s an opportunity.

We have 1 big horizontal bet and 2 vertical bets with service and CRM. We’re going all in on all 3, and I’m very confident about that. I think it’s a big bet, and we’ll do whatever is necessary to capture that opportunity.

Harry Stebbings

Who’s the harder competitor, HubSpot or Salesforce?

Eran Zinman

Again, the question is: who’s going to be able to change? That’s the most important factor for me. At the end of the day, it’s not what they built, but how they can change.

Going back to my point about the public market, I think this is where companies are mispriced. Everybody’s priced now on the downside, but it’s because of a lack of information—not because the market is not sophisticated enough, but because you don’t know who’s going to be able to change.

I’m confident we will change. There are a lot of questions about how and a lot of risk to it, but we’re going to change. The question is who else is going to change, and who else is going to change successfully and responsibly?

Harry Stebbings

Who do you think will change more effectively, HubSpot or Salesforce?

Eran Zinman

Being in a bigger company is harder because it’s hard to move humans. That’s the hardest part. I think people think enterprise is a benefit. Maybe SMBs are better because SMBs are more open to adopting new technologies.

When you play defense, some of those things might look like disadvantages—selling to SMBs or being a smaller company. If you play offense, those disadvantages might become advantages because those customers might be sooner to adopt technology and will buy those products before enterprises will buy them.

I don’t know, to be honest. It’s for them to prove. I will never underestimate either of those companies because they’ve built incredible things. In general, I think investors underestimate incumbents’ ability to change, their willingness to change, and their motivation to change.

Those companies reached where they are because of multiple things, and they’re very successful companies. I think the cycle is going to shift. Once you see another public company change and accelerate, and another one accelerate, investors are going to say, “Hmm, it happens. So let’s rethink who else is going to change over time.” Valuations will go up.

Harry Stebbings

What do you say to people who say that the babies are being thrown out with the bathwater?

Very strange analogy, but it's kind of what they say in the public market. Other than Monday, what is the biggest baby being thrown out with the bathwater?

Eran Zinman

I don't know. I think most of them—it’s not like, again, I'm not an investor, so I don't have my own list. I think it's been a bloodbath, so it's really hard to pick.

Harry Stebbings

Who's under?

Eran Zinman

Yeah, it totally has been.

Harry Stebbings

Listen, I want to do a quick fire around you. I say a short statement, you give me your immediate thoughts. What have you changed your mind on in the last 12 months? What did you think that you maybe don't, or what didn't you that you now do? What's been the biggest mindset change?

Eran Zinman

Obviously, AI. A year ago, I didn't understand—I’ll be honest, I don't think I was the only one—but I didn't understand the magnitude of the change. Today, I understand that software has fundamentally changed forever. That's something I didn't understand, but now I totally get it, and it's obvious to me that the future is going to be very different for software.

Harry Stebbings

What criticism about you stings because it's partly true?

Eran Zinman

About myself?

Harry Stebbings

Yeah.

Eran Zinman

I think one thing that we can do better is tell our story in a better way. Roy and myself—we're not, even though we do great marketing for our product, I don't think we tell the story well enough for the company, and that's definitely something that I feel we can improve.

I often feel like, if people knew what I knew, they would be much more confident in Monday and where we're going. I feel it's my responsibility to do a better job telling our story and our strategy.

Harry Stebbings

OpenAI at $500 billion or Anthropic at $380 billion—which one would you rather be an investor in?

Eran Zinman

First of all, I think we all need a little bit of humility. What I've heard in the last year is, “Microsoft is the most amazing company.” “Microsoft is finished.” “Google is finished.” “Google is the best company on Earth.” “OpenAI is the most amazing company.” “OpenAI is finished by Anthropic.” This is like 3-month cycles.

I feel it's like 1998, and we say, “Yahoo and Netscape are going to suck all the value from the internet revolution,” and we know nothing. I feel we're in the beginning of an exponent. We don't know. It's really hard to say who's going to win and who's going to lose.

It's a horse race, and I think we're probably missing 90% of the picture of how it's going to play out. So I don't know. I'm not an investor. I'm making bets on Monday, not on other companies.

Definitely, I feel Anthropic has a little bit more momentum right now. That can change, and it will change, I'm sure. So I don't know, to be honest.

Harry Stebbings

The trouble is, when you don't know, we don't know and no one knows. And the trouble then is, it's a flight to safety and a flight to cash. That's the problem that I think we're going to see now, which is, no one fucking knows, and so no one wants to play the game.

I've had enough of casino roulette in the public markets. Fuck this. I'm selling, and I'm just going to cash. That is what you're seeing everyone do: a movement to cash.

Eran Zinman

Yeah.

Harry Stebbings

Warren did it brilliantly with Berkshire 6 months ago. That's a problem for us, though, because we need that cash in Monday.

Eran Zinman

Yeah, yeah. But look, it's a cycle. What happens in the cycle is that, over time, you see consistency and you gain confidence. Then you see companies accelerate and you gain confidence.

Nothing I will say will change perception. Time and execution will change perception, and this is our responsibility as CEOs. This is what I'm planning to do. Over time, it will change. It's a cycle. I've been through so many cycles so far.

Harry Stebbings

Is this the hardest one, or is this like every other one?

Eran Zinman

Look, everybody enjoyed the 2021 cycle with COVID, right? But it was also a cycle. I remember when our stock went up to $400 after we IPOed, and one of our investors, Ken Fox from Stripes, told me something which was brilliant. He told me, “Isn't it great that the stock is going up without the revenue going up?”

I said, “What? What are you talking about?” And he said, “Yeah, everything you gained is through a sentiment change. Nothing you've done.” It really resonated with me. I said, “Okay, I need to distinguish between what we do as a company and our growth and the market sentiment.”

If you don't praise yourself when the stock is high, you won't be impacted when the stock is down. If you don't attach your personal success and personal ability to lead a company to the sentiment, then you need to focus on the business performance. That was his point, and it really resonated.

I didn't celebrate when it went up to $400 because I knew it was temporary. At the end of the day, it's a cycle. Everybody enjoys it when the cycle is up, but now, when the cycle is down, I need to focus on the business metrics—the revenue, the retention, the things we are doing. That's the important part, not being carried away by the cycle itself.

Harry Stebbings

Totally agree with you, and 100%—very difficult to do. That's where I like the experienced CEO that you are, in terms of having seen many before. I think it's actually where younger CEOs struggle, where it's the first cycle and the depths are so low and the highs are so high when it's the first time you've done it.

Which other CEO do you most respect and admire? When you look across the board at your counterparts, which one makes you think, “I want to be like them?”

Eran Zinman

Yeah. So, of course, and again, it's a personal friendship, but I really love Avishai from Wix and Nir. I feel like we're close friends, so obviously I ask them a lot of questions. But we also have other CEOs that I talk with, and again, it's hard for me to pick a name because I don't know them personally.

When you pick somebody, you take their entire personality with it, so it's really hard for me to pick. But look, the amount of information that I acquire through podcasts, blog posts and videos—I probably acquire 5 or 6 hours of content a day.

I walk to work, I walk back, I do the dishes. My kids are saying, “Why do you have the AirPods in your ear all the time?” I just feel we need to learn like crazy. I try to gather as much information as I can, and I think I learn a lot from different people's perspectives.

Also, I love the show you guys are doing. The 4 of you—the 3 of you, sorry. So, I listen to that. Now you need to be learning as much as you can. That's the mode I operate in.

Harry Stebbings

I'm adding in a penultimate one. What's your biggest marriage advice when you go through a really tough time as well? It's very difficult for you, and it puts a strain on marriage. What's the biggest marriage advice? Advise me.

Eran Zinman

Are you getting married or not yet?

Harry Stebbings

Not yet. But you know women.

Eran Zinman

Yeah. Well, first of all, I've been with my wife for 23 years now, so we basically grew up together. But I'll tell you one thing: my wife has been nothing but amazing throughout this journey, and specifically, I would say, the last 6 to 8 months.

It's not like she doesn't care. She knows what I'm going through. The amount of support I got is unbelievable. One piece of advice I would give—and this is actually from my therapist—is that she gave it to me because I told her what I told you now about my wife.

She told me, “Say it to her. When you meet her this evening, say to her what you said to me.” I said, “Right, I mean, I have to, because I feel it, but I haven't said it to her.”

I think communication, sharing how you feel—the good and the bad—and talking about it is the best advice I can give, with my wife and also with the partners at work. I feel the more you open up, the more vulnerable you are and the more you share, the more intimacy you create and the better relationship you create with other people.

Harry Stebbings

Very un-English of you. We tend not to share much in the bedroom. Yeah, yeah, yeah. We're very uncomfortable. We normally call each other “Mister” and then the surname. It's like Mr. and Mrs. Stebbings.

Final one, dude. What are you most excited for in the next 10 years? My mother's got MS. I'm super freaking excited for advancements in MS treatment because of AI and everything that we're seeing with longevity. What are you most excited for?

Eran Zinman

This is probably the biggest change since the invention of computers that we're experiencing now. I'm lucky to be part of that, and I'm excited to see how this plays out.

I think if you ignore the negativity attached to that, it's pretty exciting. It's quite a period to be alive. It's pretty amazing.

Harry Stebbings

When you think about civilization and how, for 1,800 years, it really remained relatively flat—feudal systems, farming-based economies—and when you look at the last 200 years, I know it's a large amount of years now, but proportionally it's not at all. God, I'm so grateful we're living in this time. How freaking epic is this?

Eran Zinman

Amazing.

Humans didn't shower in hot water 80 years ago. Now, if you don't have hot water in your bath before you go to sleep, it's like it ruined your day.

We get used to good things so easily. I think, specifically with AI, we're going to get used to getting the best treatment, the best doctors—everything is going to be instant. Each one of us is going to have the most amazing personal assistant.

Our life is going to be amazing. And, of course, we're going to complain. Of course, we're going to look at the things that don't work. But I think going forward, probably the value and the quality of life are significantly going to go up.

Harry Stebbings

Dude, as I said, I so appreciate you taking the time. I so appreciate you putting up with the harder questions. You've been fantastic. So, thank you so much, man.

Eran Zinman

Thank you, Harry. Thanks for having me.

Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Eran Zinman | BidClub