The verdict
Both are genuinely good, and neither is a wrong answer. But they pull in different directions.
ClickUp is the value and capability play. A free tier with unlimited members, a 7 USD floor, and more views than you'll ever use mean it consolidates several tools into one bill, which is exactly what a bootstrapped team wants. The cost is real, though: it is configurable to a fault, and you can lose a weekend tuning it before anyone tracks a task.
Monday is the adoption play. The board model is the easiest thing here for a cross-functional, non-technical team to pick up without a training session, and its native HubSpot, Jira and Salesforce links suit a B2B stack. You pay for that polish, a 9 USD floor, annual billing, and a 3-seat minimum that bites the moment you're three people.
For a lean founder watching every seat, I lean ClickUp. For a small team that needs everyone productive this week without a setup project, Monday earns its premium.