Scale Like a CEO: Transitioning to SaaS & Building Leadership Culture with Dean Curtis

12/12/2025 17 min Temporada 1 Episodio 61
Scale Like a CEO: Transitioning to SaaS & Building Leadership Culture with Dean Curtis

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Episode Synopsis

Most decks drain attention; the best stories drive decisions. We sit down with Dean Curtis, CEO of Ingage, to unpack how a services agency transformed into a focused SaaS company by turning sales content into interactive, data-driven experiences that prospects actually remember. Dean shares the messy middle of building go-to-market while the product was still taking shape, the moment they chose a single vertical in home services, and the downstream effects of that decision on retention, revenue quality, and roadmap discipline.We get tactical about leadership. Dean explains how stepping from CRO/COO into the CEO role forced him to stop being the doer and start building the people who build the business. He walks through hiring for curiosity and ownership over resume length, replacing leaders as growth ceilings changed, and anchoring culture on two simple values: customer first and value focused. The conversation gets real on feedback: how he rebuilt one-on-ones around the employee’s agenda, required unfiltered two-way critique, and learned to ask clarifying questions instead of shutting ideas down. Psychological safety didn’t appear overnight; consistency and grace made it stick.Alignment is a system, not a slogan. Dean outlines the OKR backbone, quarterly onsite planning, monthly business reviews, and a candid weekly update video that surfaces wins and misses across teams. He also breaks down the 1080-10 leadership framework: set the first 10% with a clear definition of done, empower the team to own the middle 80%, then return for the final 10% to raise the standard. It’s a practical playbook for SaaS founders and operators who want product market fit, accountable teams, and a culture that scales.If this conversation gave you a useful tactic or a new lens on leadership, follow the show, share it with a teammate, and leave a quick review so others can find it. Got a PMF story or a feedback ritual that works? Send us a note—we’d love to hear it.

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