EPISODE · Apr 13, 2026 · 48 MIN
From $5M to $500M: How a Serial CMO Thinks About Marketing
from Scaling B2B · host Mendel Cohen
Steve Keifer — CMO at six B2B SaaS companies, several of which hit hyper-growth and billion-dollar valuations — breaks down exactly how to build, structure, and scale a B2B marketing org. From who to hire first to why most companies keep churning CMOs every 18 months, this one is packed.Key moments:[3:03] Why hiring for one CMO archetype is a trap — and the "college sports transfer portal" model breaking B2B orgs[8:25] The first hire every CMO should make and why it's not the most strategic one[9:45] The 40-function skills matrix — how to decide what stays in-house vs. what goes external[14:01] What a marketing org actually looks like at $5M vs. $50M ARR[17:59] Why source-based ROI attribution is broken — the NFL analogy that explains it perfectly[23:38] Blue ocean vs. red ocean content — and why most B2B teams are copying each other into irrelevance[35:45] How a seasoned CMO is using AI tools today (AirOps, Profound, Clay) — and still feels behind[43:15] What Steve is telling his SDRs about AI: "Embrace this if you want to have a job"
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From $5M to $500M: How a Serial CMO Thinks About Marketing
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