About this episode

Michael and Matt discuss their transition from individual contributor roles to management, the challenges of email marketing, and the development of an AI-powered digital asset management system.

Michael opens on a milestone he didn't expect to feel so strange: he's up to nine people, four of them in the last month, and for the first time his job is almost entirely infrastructure and people management. The individual contributor work is almost gone — except sales calls, which he's starting to find numbingly repetitive and knows need to be handed off. Matt's feeling the same fatigue on the other end of a late, no-show customer who turned a routine call into one of his worst sales performances in a year. Both are building toward something that doesn't require them in every seat — and starting to feel the gap between where they are and where that actually is. On the marketing and sales side, Michael is deep in email marketing infrastructure — building a Klaviyo MCP server so Claude can write and push campaigns without him touching the interface — and is watching Meta ad fatigue eat into ROAS in real time while he's too buried in production to film new creative. Matt's EA Trish is now handling invoicing so well that month-end close happened the day after month end for the first time in Develop history, and he's down to under two hours a week in accounting. Matt also debuts…

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