Is Monday THE Operating System for Work?

Monday.com sits right in the middle of this transformation, and if management gets its way, it won’t just be a participant. It wants to be the work operating system for the modern enterprise.

For companies running cross-functional projects, think engineering, sales, marketing, and operations all under one roof, Monday offers a centralized dashboard where tasks can be assigned automatically, progress tracked in real time, and bottlenecks spotted before they derail timelines. In effect, it promises to turn scattered, siloed efforts into coordinated execution.

But while Monday has been a darling of small businesses, the real money is in large enterprises, and breaking into that market is more complex than simply offering a free trial.

Key Points

• Monday.com is targeting Fortune 500 adoption through deep integrations and vendor consolidation.

• $1.5B cash, no debt, and margins expected to rise from -2% to +10% by 2029.

• Competitive market, but success in enterprise scale and AI differentiation could deliver big gains.

From SMB Darling to Enterprise Contender

Monday’s early growth came from a self-serve model, which allowed anyone with a company credit card to sign up and start managing projects. That works for freelancers and small teams, but it’s not how Fortune 500 IT departments buy software. Enterprise deals require procurement approvals, security audits, compliance checks, and integration with sprawling internal systems.

Recognizing this, Monday pivoted to a hybrid go-to-market approach, adding a direct sales force aimed squarely at decision-makers inside large corporations. The shift has paid off and revenue from enterprise accounts with over $100,000 in annual recurring revenue has jumped from just 5% of total sales in 2020 to roughly 20% today.

Still, that leaves the company heavily weighted toward smaller customers, which are inherently less sticky and more price-sensitive.

For context, Smartsheet, arguably Monday’s closest competitor, already has about 1,900 enterprise customers in that $100,000+ ARR bucket, compared to Monday’s 833. That gap tells us Monday is behind in penetration, but also has a clear runway to catch up.

Why Consolidation Could Be Monday’s Secret Weapon

Most large companies today use multiple work management tools simultaneously. It’s not uncommon for marketing to be on Monday, engineering on Jira, and operations buried in Asana.

While that fragmentation may sound like a problem, it’s actually an opportunity because as organizations try to standardize processes and cut software costs, they will inevitably consolidate vendors.

If Monday can position itself as the one platform to rule them all, it stands to win big. That means building out enterprise-grade security, deep integrations with systems like Salesforce and ServiceNow, and compliance certifications that make IT teams comfortable.

Monday has already shown a willingness to play nice with big tech, partnering with Microsoft 365 rather than trying to displace it, which could help it slip in through the integration door rather than fight incumbents head-on.

Where the Moat Could Come From

Once Monday is tied into a company’s workflows and linked with other mission-critical apps, ripping it out becomes painful and costly.

 The company’s growing third-party app marketplace could become a self-reinforcing ecosystem, more users attract more developers, and more developers create more tools that attract more users.

Plus, if Monday can leverage AI to automate more of the project management drudgery (auto-assigning tasks, predicting bottlenecks, generating reports), it could widen its functionality gap over competitors.

Management’s playbook is straightforward with expected compound annual growth rate of 24% through 2029, driven by higher average contract values, upselling existing customers, and winning more enterprise deals.

Risks You Shouldn’t Ignore

Even with these tailwinds, Monday is not without hazards. For example, giants like Microsoft could decide to get aggressive in this space, bundling work management into existing subscriptions at little to no extra cost.

And with 70% of revenue still coming from smaller deployments, macroeconomic slowdowns could cause significant churn.

At a double-digit price-to-sales multiple, the market is pricing in rapid, sustained growth. Any stumble could lead to a sharp multiple contraction.

The Bottom Line

Monday.com is in the middle of a high-stakes transformation. If it can climb the enterprise ladder, deepen integration stickiness, and ride the wave of vendor consolidation, its future could look very different from its past. But the window for establishing dominance in this crowded space is closing fast, and the competition isn’t standing still.