Eran Zinman, Co-Founder & Co-CEO @Monday.com: Going Upmarket, International and Multi-Product |E1247

Summary

• The heterodox core of Monday’s playbook: optimize for cash, not SaaS metrics. “LTV, CAC, ARR — they never mention cash,” so Zinman built the funnel around cash-on-cash speed — annual prepay A/B tests, campaigns ranked by payback velocity, even negotiating 90-day payment terms with Facebook and Google — recycling $5M of raised capital into a $15M performance-marketing budget. “Our customers have been the biggest investor of Monday — more money than we ever raised from investors.”
• The growth investors missed: $6M→$18M→$50M→$120M ARR in three years, yet Monday got “a lot of nos in our A, B and C rounds” because low ACV, SMBs, churches and hotels pattern-matched to “you can’t make money selling to SMBs.” Avi at Entrée Capital bridged them with a convertible after they spent 70-80% of the seed — “I believe in you guys even though I don’t know why” — which Zinman calls a pivotal moment; the A was ~$7.5M at ~$3-4M ARR, the B $25M from Insight at ~$100M pre.
• The reframe that changes the multiple: “we built the equivalent of force.com” — a generic platform, not a work-management tool, with work management merely the first implementation. Tens of thousands of accounts built full CRMs on Monday boards unprompted; the packaged CRM went ~0→$25M in one year, “growing faster than what Monday did back in the days,” and Monday crossed $1B ARR roughly three months before this recording.
• Performance marketing has a ceiling: at $50M ARR they built a “road to 1 billion” dashboard (target 2023, missed by one year), ran the math, and concluded the engine couldn’t carry them — at $1B growing 30%, the majority of revenue needs to come from existing customers. That forced the reversal of “we’re never going to have a sales team” at ~$40-60M ARR; the sales org is now 1,000+ people, added as a layer on the SMB pyramid, not a pivot to enterprise.
• On AI disrupting horizontal SaaS, Zinman is unbothered by the agent-as-frontend scenario: “I don’t think anybody will be willing to put their future into an AI bot” without dashboards and the ability to question the data — systems of record survive even if the work moves. But pricing changes “for sure”: seat-based models must shift “more focused on consumption in addition to seats.”
• The founder operating system: fail fast as reaction to a first startup killed by fear of failure (“the reason I failed… is that I was afraid to fail”), personally avoids email (“I never got anything good out of an email”), never surprise the board — a daily automated SMS of metrics meant directors “knew the numbers better than I do” — and attack pain directly: “if something is very painful, that’s the right time to get into it and fix it.”

Deep dive

1. The first startup died of fear — so failure became the DNA

• Before Monday, Zinman spent 14-15 months building a user-review search engine, felt he wasn’t ready to launch it, ran out of personal money and energy, and closed it. The post-mortem: “the reason I failed in that company is that I was afraid to fail” — afraid of TechCrunch write-ups, of critical users. The feedback he finally got after 14 months was feedback a mockup would have earned on day one.
• The vow carried into Monday verbatim: “I’m going to fail often, I’m going to be happy about failure” — try it out, A/B test, learn as fast as possible. The deeper cut, from the kid who was smart in school and university: “nobody cares about your achievement or knowledge… it’s all about the product — is it good enough, do people really want it.”

2. The founding insight was a vacuum, not a new idea

• Zinman and Roy (then at Wix) deliberately inverted the usual founder instinct of hunting for an unthought idea. Their question: CRM has Salesforce — “who’s the number one vendor that people rely on to manage the core of their work?” “There was none.” A packed category with no dominant player read as a huge vacuum, not a red flag.
• Because neither considered themselves great managers, the day-one principle: nothing in the product is rigid — “our own customers build their own product on Monday.” That choice becomes load-bearing for everything that follows.
• The start was rough: eighteen months focused on communication (the Yammer/HipChat, pre-Slack era) produced a nice-to-have. With 70-80% of seed spent, two developers who “always felt we’re one feature away” did the unnatural thing — stopped coding and interviewed customers about how they manage their businesses — and pivoted to flexible work management. The first unassisted paying customer triggered a Homer Simpson “woohoo” on a wall-mounted TV counter; at ~$12/seat, “we never talked to them… it just felt like we built something that can turn into a machine.”

3. Investors said no at A, B and C — the convertible that saved it

• The company raised $1.4M for the A at $2M pre (“30% of the company”). After spending 70-80% of the seed without product-market fit, the standard move is to send the founders out to “try their luck.” Instead Avi at Entrée Capital said: “I believe in you guys even though I don’t know why… don’t do an A round, I’ll give you the money, let’s do a convertible.” Zinman calls it pivotal because the runway helped leverage existing momentum.
• Harry’s reconstruction of the investor logic — low ACV, SMB, selling to hospitals and churches, “you can’t make money selling to SMBs” — and Zinman’s concession: “I always felt it’s all temporary, eventually we’ll go upmarket… maybe we didn’t communicate well enough to investors.” The A landed at ~$7.5M with ~$3-4M ARR; the B was $25M from Insight at ~$100M pre on $7M ARR — better, in his view, because Insight could follow on and “really understood the potential.”
• The growth that followed — 6→18→50→120 in three years — also included taking Jason Lemkin literally: 1→10 in four quarters, 10→100 in five or six. When they finally met, Lemkin explained he’d been describing the very best companies. “I took it as granted — literally this is what we need to do. I guess ignorance is bliss sometimes.”

4. Big Brain: optimize for cash, not SaaS metrics

• Against the temptation of off-the-shelf analytics, they built Big Brain internally — “we said we’re going to build a huge company, I don’t know where we got the confidence” — tracking every click, every ad view, through signup, conversion, and expansion.
• The heterodox part, which Zinman flags as the thing founders get wrong: “a lot of SaaS metrics are optimized not for cash… LTV, CAC, ARR — they never mention cash.” Monday optimized cash-on-cash speed: A/B tests pushing annual prepay, campaigns selected by payback velocity, faster onboarding and payment flows — and on the expense side, asking Facebook and Google to defer payment 90 days.
• The result: $5M of raised money recycled into a $15M performance-marketing budget. “Our customers have been the biggest investor of Monday — more money than we ever raised from investors.” The machine still runs — in 2023 spend was around $17M a month (“a little bit less but around that”) while the company sat over 25% free-cash-flow positive.
• Channel philosophy: no spray-and-pray (“I pray sometimes, but it doesn’t help you with performance marketing”). Facebook came first and delivered churches, hotels, retail, airplane manufacturing — 70% of customers are non-tech, which “opens up the TAM.” He refuses the “least effective channel” question: Google captures intent, Facebook and YouTube capture latent demand — different audiences, both convertible. The dapulse→Monday rebrand was itself a marketing decision: with “about five seconds of attention,” you need a name people remember. And yes, CRM is among the most expensive AdWords — “but it’s very cost effective for us.”

5. The sales-team reversal, and the math that forced it

• Roy and Eran had declared “we’re never going to have a sales team.” At a New York board meeting around $40-60M ARR: “look, we’re probably wrong.” The trigger wasn’t ideology but unmet demand — enterprise customers “knocking on our door saying we want to scale, and there was nobody around to help them,” wanting security, governance, onboarding, a relationship. Today the sales org exceeds 1,000 people.
• On the standard advice to wait until you’re pulled upmarket: it worked for them, but he flips the warning — a great early VP of sales “can sell anything even if your product is really crappy — that’s a curse,” because Monday worked so hard to improve the product, retention, and marketing machine.
• The strategic distinction he insists on: Monday didn’t pivot to enterprise, it added the tip of the pyramid while keeping the SMB and midmarket base — unlike companies that give up on converting smaller customers and chase high ACVs.
• At $50M they mounted a vertical “road to 1 billion” TV in every office, target 2023 — missed by one year. The math behind it: performance-marketing spend required to hit $1B “didn’t add up,” and at $1B growing 30%, “the majority of revenue needs to come from existing customers.” Hence sales plus expansion, not a better ad engine.

6. Not a product — the force.com of work

• The thing Zinman thinks investors got wrong from day one: “we didn’t build a work management or project management tool… we built the equivalent of force.com” — generic building blocks, with work management merely the first implementation. Marginal cost of packaging the platform as CRM, Dev, or Service is minimal against the compound value of shared data, automations, and processes.
• Multi-product came remarkably late — the second product only ~2.5 years ago — and he defends the sequencing (“maybe we could have done it sooner, but it was the right decision at the time”). The demand was already proven: tens of thousands of accounts had built full-fledged CRMs on Monday boards themselves, because “we want control” and the cost and complexity of customizing Salesforce-class enterprise software pushed them away. Monday CRM went ~0→$25M in a year per the last investor day, “growing faster than what Monday did back in the days”; Monday crossed $1B ARR about three months prior.
• The hard-won multi-product lesson: “it’s not just about the product — go-to-market is as important, and every product has a very different go-to-market… different buyer, different decision process, different way people consume ads.” Each product runs as its own business unit with dedicated marketing and sales — “like small startups within the company.” Five years out he expects CRM “very dominant,” Dev growing, and Monday Service momentum that’s “unbelievable.”
• Competitive set — HubSpot, Salesforce, Zoho on CRM; J Service, Freshdesk, some ServiceNow on service — doesn’t faze him: entrenched incumbents people pay heavily for are “an opportunity to disrupt that market.” After the stomach-knot of reading TechCrunch during his first startup, he swore off competitor-watching: “I’m just going to focus on myself and my journey.”

7. AI: the system of record survives, the pricing model doesn’t

• On agents reducing Monday to a database that AI reads and writes: “I think it’s an amazing thing.” His reasoning: “I don’t think anybody will be willing to put their future into an AI bot without having the ability to question what’s going on, see dashboards, graphs and all the data.” Work may migrate to AI; the need to track, see, and analyze it doesn’t — plus “a substantial human element” remains. Rather than a dedicated AI product, Monday lets customers wire AI into their own workflows, the same customization principle as everything else.
• On pricing he’s categorical: AI changes it “for sure” — as AI replaces human labor, seat-count pricing “should adjust and maybe be more focused on consumption in addition to seats.”

8. The $7.5B IPO, as anticlimax

• The decision was “more random than you might think,” but the logic: the most inspiring SaaS companies were all public, and being public “adds a layer of maturity.” Two surprises since: public-market investors are “way more sophisticated than what I thought,” and the quarterly earnings cadence is a feature, not a burden.
• The day itself, as told: one of the first in-person IPOs after COVID lockdown, roadshow all on Zoom; by 5pm he and Roy were literally alone at NASDAQ, took off their matching blazers, walked 25 minutes to the hotel in white t-shirts, and he “sat down on the bed and just stared at Netflix for like 3 hours.” The stock rose 10-15% day one — but it only felt real the next morning, adding Monday to his iPhone Stocks app: “I felt it throughout my whole body.”

9. Co-CEOs who walk home together, a board that’s never surprised

• The co-CEO structure started informally — Roy was CEO, Eran CTO, until a week in Roy said “I want us to do everything together.” They’d alternate roles in investor meetings until making it official just to stop the confusion. The reason it works: “he has no ego… we both want to do what’s best for the company.” They still walk home together in Tel Aviv almost every day, “hours just to think and talk.”
• Board management rule one: “never surprise the board — that’s the worst thing you can do.” Big Brain sent directors a daily automated SMS of company performance, good or bad — “they knew the numbers better than I do” — and every decision was pre-wired in individual calls “so we talk more about the future than waste time on disagreements.” Harry, audibly taking notes for his own fund: “one to think about.”
• The quickfire distilled his operating system: set goals from what you want to achieve, not what you can do (“bottom-up plans are last year with small adjustments”); personally avoids email — “I never got anything good out of an email… when you start being managed by external tools, it’s a huge distraction”; and run at the pain: “founders 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.”
• The change of mind worth noting: years of imbalance ended with therapy, and the therapist’s line that “hit deep” — an exhausted, stressed leader “reflects on everybody else.” His conclusion: “I should treat myself like a professional athlete — I should be at my peak all the time.” The baby usually wakes him around 6am, he tries to exercise every morning, and he got an Oura ring.