This is about monday.com, whose software works like Lego blocks—users can build any workflow, not just project management. The guest thinks its flexibility lets it thrive despite competition, and it could become the next software platform. Key holdings: monday.com (revenue over $1B, biggest customer grew from 7K to 80K seats, bullish), Salesforce (a comparison, grew faster earlier), and ServiceNow (high retention with large accounts).
monday.com is a work management software platform founded in February 2012, with a current market capitalization exceeding $14 billion. This podcast features Ben Hensman, portfolio manager of the Square Peg Global Technology Fund, who analyzes its path to success: monday.com has evolved from a simpl
Ben Hensman (Portfolio Manager of the Square Peg Global Technology Fund) analyzes monday.com's growth trajectory from its founding in 2012 to the present. The core argument is: monday.com's "Lego brick" product methodology — built on a flexible, schema-free database architecture that allows customers to freely assemble their own workflows — is the foundation of its successful expansion upmarket, its ability to surpass traditional project management software, and its potential to become the next-generation software platform.
Ben Hensman believes that monday.com's core differentiation lies in designing its product as "Lego blocks of software" rather than fixed-function software packages.
Historical trajectory: Founders Roy and Arun incubated DePulse (monday.com's predecessor) from within Wix.com, initially used for internal project management at Wix. It officially launched as a standalone product in 2014, with an ARR of just $400,000 that year, reaching $6.5 million by 2016, then growing 10x over the next three years, and another 12x over the following five years to exceed $1 billion in ARR.
Mechanism breakdown: Traditional software (e.g., Salesforce, HubSpot) uses rigid data schemas, forcing customers to use the product in a predefined manner. monday.com, by contrast, builds a schema-less database architecture called MondayDB, allowing customers to arbitrarily assemble workflows via drag-and-drop, custom columns, and automation. Hensman's analogy: "Think of Monday as Lego blocks of software that you can construct and work in any way that you want to."
Data support:
Unique insight: This flexibility means monday.com's competitors are not a single category but span three battlefields: "Project Management" (Asana, Trello, ClickUp), "Functional Software" (Salesforce, ServiceNow, HubSpot, Microsoft), and "Flexible Platforms" (Notion, Airtable). Hensman argues that it is precisely this "continuous innovation within a red ocean" that has allowed monday.com to continue growing against the tide after the funding retreat.
Hensman emphasized that what truly enables monday.com to move from SMB to the enterprise market is its proprietary MondayDB database architecture.
Technical logic: Traditional software follows a "UI calls a fixed database" model, while monday.com treats the "database itself as the product." MondayDB adopts a schema-less, columnar + row-based hybrid storage approach, allowing customers to instantly customize workspaces at any scale. Hensman explained: "It is the database. They built a proprietary schemerless database architecture that allows users to instantly customize the workspace."
Historical milestone: In 2019–2020, when monday.com was still primarily serving SMBs, MondayDB had not yet been completed. The subsequent upgrade of this database enabled it to support boards with "hundreds of thousands of items and columns," a prerequisite for entering the large enterprise customer segment.
Inference: Hensman believes that MondayDB is the key differentiator between monday.com and other flexible platforms (such as Notion and Airtable)—the latter may encounter performance bottlenecks when scaling, whereas monday.com has already solved this issue.
Hensman points out that monday.com's enterprise customer expansion path is "starting with a single team, leveraging product value for natural diffusion, and ultimately achieving top-down sales," rather than directly targeting large enterprises from the outset.
Data chain:
Mechanism breakdown: Hensman summarizes the growth drivers as five levers — seat/team expansion, usage tier upgrades, product cross-selling (CRM, Service, Dev), geographic expansion, and pricing adjustments. In 2024, pricing adjustments alone contributed approximately $30 million in incremental revenue (about 4 percentage points of growth).
Sales model evolution: In 2019, 70% of new ARR came from self-service; by 2024, that ratio had fallen to 40%, with the sales team and partners accounting for 40% and 20%, respectively. The partner channel grew from 12% in 2019 to 20% in 2024, replicating the ecosystem models of ServiceNow, Salesforce, and Atlassian.
Hensman believes that AI represents both a major opportunity and a business model risk for monday.com, with the core question being whether the company can shift from "per-seat billing" to "value-based billing."
Three AI products:
1. AI Blocks: AI functions embedded in board columns (classification, extraction, summarization, translation). Usage surged from 3 million/quarter in Q3 2024 to 14 million/month in January 2025.
2. AI Power-Ups: Specialized AI tools on various products, such as predictive risk management.
3. AI Digital Workforce: Function-based AI agents, the first of which is "Monday Expert" – enabling users to customize boards and build workflows via natural language. Sales and service agents will follow.
Risks and opportunities:
Hensman's distinctive insight: monday.com's AI Digital Workforce products (such as Monday Expert) are essentially "self-service discovery tools" – they help customers identify use cases they were previously unaware of, thereby smoothing the expansion process. This could be the mechanism by which AI accelerates growth rather than erodes revenue.
Hensman argues that monday.com's financial efficiency and growth quality place it in the top tier among comparable software companies.
Key data:
Pricing and valuation:
Hensman's comparison: Salesforce in 2010 (approximately $1.2 billion in revenue, similar margin structure) had a multi-year forward NDR of ~130%, and ServiceNow was similar. monday.com's current NDR is 115%, and Hensman believes it has the potential to rise back to higher levels.
Hensman believes that monday.com's arena definition far exceeds 'project management' — it targets 'any workflow in any enterprise', theoretically with no upper limit.
Market Definition:
Competitive Landscape: Hensman divides it into three categories — 1) project management (Asana, Trello, ClickUp); 2) functional software (Salesforce, ServiceNow, HubSpot, Microsoft, Atlassian); 3) flexible platforms (Notion, Airtable). He believes monday.com's flexibility allows it to 'span all three and surpass them', and its gross retention rate for large customers has approached ServiceNow's 95-97% level.
Hensman's Warning: The article acknowledges that 'this has looked like a red ocean', but emphasizes that monday.com continues to break out through execution and product speed, especially investing counter-cyclically and capturing market share after the 2022 funding downturn.
| Ticker | Guest Sentiment | Key Data |
|---|---|---|
| monday.com | Bullish – potential to become the next-generation software platform | 2024 revenue over $1B, NDR 112%, Enterprise NDR 115–116%, FCF margin 25%, Rule of 60 at 64% |
| Canva | Customer case – positive | Marketing production time reduced 40% after using monday.com, creative output increased 3x |
| McDonald's | Customer case – positive | Reduced internal emails by 20,000/month, saved 1,200 hours/month (~7 FTEs), ROI ~6x |
| Bloomberg | Customer case – positive | Deep integration using monday.com API, rapidly resolved cross-project issues |
| Salesforce | Competitor / Comparison benchmark | ~$1.2B revenue in 2010, similar margin structure, NDR once reached 130% |
| ServiceNow | Competitor / Comparison benchmark | Enterprise gross retention 95–97%, NDR once reached 130% |
| HubSpot | Competitor | Fixed data model, competes with monday.com's CRM product |
| Asana | Competitor | Project management track, but overtaken by monday.com |
| Atlassian | Competitor / Ecosystem reference | Similar ecosystem model |
| Microsoft | Competitor | Offers similar AI capabilities, but in the form of "copilot layered on top of fixed software" |
| Notion | Competitor | Flexible platform, but different form factor |
| Airtable | Competitor | Flexible platform, but different form factor |
1. “monday.com is the database itself, not the software interface that calls the database” (Ben Hensman) — This is the fundamental difference from traditional SaaS like Salesforce and HubSpot: users directly operate the underlying database, enabling arbitrary customization without a middle layer.
2. “In 2019, only 76 customers had annual spending over $50,000; by 2024, it reached 3,200, a 40% growth — and the largest customer jumped from 7,000 seats to 80,000 seats” — Validates the authenticity of the expansion path of “natural diffusion from a single team,” which is more sustainable than top-down sales.
3. “monday.com’s CRM product was built by only 4 engineers and now has 27,000+ customers, with annual growth exceeding 100%” — Supports the argument that “speed and efficiency are core culture,” and also proves that platform flexibility reduces the cost of new product development.
4. “The 2024 pricing adjustment contributed approximately $30 million in incremental revenue (about 4 percentage points of growth), and the churn rate reached a historical best” — Validates the core value of monday.com’s products to customers, who are willing to pay higher prices.
5. “AI Blocks usage jumped from 3 million per quarter in Q3 2024 to 14 million per month in January 2025” — Shows rapid customer adoption of AI features, but Hensman reminds: “AI Digital Workforce” is the biggest potential, and it also means the business model needs to shift from “per seat” to “per consumption + ROI.”
6. “monday.com’s net dilution is only 1.8%, far lower than the difference between GAAP operating margin and Non-GAAP (13-14% from stock-based compensation)” — Indicates that the company effectively manages the actual dilution of equity incentives, which is crucial for long-term shareholder value.
7. “monday.com has raised approximately $800 million in capital, but most has never been used, and it currently sits on a balance sheet of $1.4 billion in cash” — Validates the founders’ obsession with cash efficiency (no free trials, prefer prepayment), which is the core reason it can achieve “Rule 60” from an early stage.
8. “After the capital ebb in 2022, monday.com was able to counter-trend increase investment and capture market share” — This is a specific footnote to “continuous innovation in a red ocean,” proving that product strength and financial discipline enable it to grow even during the industry downturn cycle.