Erik Jacobson sits down with Regina Baumgartner, Head of Content at Rippling, to explore how she manages content strategy across a complex multi-persona audience spanning HR, finance, IT, and startup teams. Regina shares the museum analogy that reframed how her team thinks about content creation and distribution: social media as street art, content series as curated exhibits, and community membership as the ultimate conversion goal.The conversation gets into what it actually takes to scale content for a compound startup, how Regina balances subscriber growth metrics with qualitative signals from community interviews, and how AI fits into a production process without killing the creative work.Key topics covered:[00:00] Intro[02:46] 95% versus 5% content strategy[04:08] Museum analogy for content vision[08:31] Content planning process and workflow[12:39] Series-based content strategy benefits[17:29] Pod structure for multi-persona teams[21:03] Cross-pollination through show and tell[23:38] Measuring content success with dashboards[26:01] Anecdotal evidence and qualitative feedback[30:50] Spy trailer webinar promotion tactic[32:34] AI-powered call scripts for BDRs[35:36] Getting to ground level with data[39:15] Studying Gong and Notion content—This episode is brought to you by Hatch.Hatch helps B2B companies build efficient content engines through video podcasts, short-form video, and YouTube. Learn more at hatch.fm.