Asana megadeals, Monday midmarket wins
Tommy Wang, Chief Business Officer at ClickUp, on the rise of the all-in-one
This points to a split market where Asana is stronger in the small number of giant, company wide deployments, while Monday is stronger in repeatable mid market and broad based enterprise expansion. A $5M to $10M software deal usually means a board level buying process, a long rollout, and a product becoming standard across thousands of employees. That suggests Asana was winning some of the highest stakes standardization decisions, even as Monday was compounding faster overall through a larger number of subscale enterprise wins.
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The customer count data fits that pattern. Asana reported 726 customers above $100K annualized revenue at fiscal 2025 year end, while Monday reported 1,756 above $100K ARR at December 31, 2025. Monday had far more scaled accounts, but that does not rule out Asana landing a few unusually large seven figure annual contracts.
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Monday's advantage was breadth and efficiency. In the interview, Monday is described as stronger in paid acquisition, channel, and land and expand in SMB and mid market. That matches Monday crossing $1B ARR in 2024 and reaching 4,281 customers above $50K ARR by December 31, 2025, which reflects a very wide enterprise base rather than a handful of megadeals.
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The product angle matters too. ClickUp describes Asana as more enterprise ready in large organizations, while Monday is framed as a flexible work platform growing fast across many teams and use cases. In practice, the biggest deals often go to the vendor that can survive security review, global rollout planning, and executive sponsorship, not just the one with the best self serve engine.
Going forward, the center of gravity is likely to move toward vendors that can do both. Monday is building the scale and product surface to chase larger strategic rollouts, while Asana needs more of those giant deployments to offset its slower growth. The winner in work management will be the company that turns team level adoption into company wide standardization without losing ease of use.