The Rebuild Moment: Why Most SaaS CEOs Are Sequencing AI Wrong | Tom Scott, Wrike

Tom Scott, CEO of Wrike, joins Stu Willson to walk through what he calls "the rebuild moment" — the actual operating playbook for a $250M+ ARR SaaS company navigating the AI transition from inside the seat. The conversation covers what's actually defensible in enterprise software when coding agents can clone a UI in a weekend, why most CEOs are sequencing the AI rebuild incorrectly, how Tom reversed his own delegation model to consolidate decision-making for speed, and what diligence questions PE investors should be asking that almost none are. Tom also walks through the J-curve of AI transformation inside Wrike's own engineering and marketing functions, including a marketing case study with concrete numbers (3x article output, 87% faster account research, 50–75% faster gated-asset production).

Keywords: Stu Willson, Stuart Willson, Just Curious, Pluris, Tom Scott, Wrike, SaaS AI, enterprise software AI, AI transformation, work management AI, AI agents enterprise, system of agency, MCP infrastructure, governance AI, J-curve AI, seat-based pricing, AI pricing models, PE software AI, private equity software, CEO playbook AI, AI rebuild, personal disruption, subtract before add, mid-market SaaS

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