Why Enablement Fails Before It Starts | Cheyenne Griffith, Deepgram

Most companies hire enablement to fix a problem enablement cannot fix. Cheyenne Griffith has watched it happen from the inside — and she has three hard gates a company has to clear before the hire works at all: founder-led sales has to be over, product marketing has to have a real point of view, and the leader has to be genuinely ready to hand over the reins. Cheyenne is building the go-to-market enablement function from the ground up at Deepgram, the voice AI company behind the speech-to-text, text-to-speech and voice agent APIs that over 200,000 developers build on. Her path there is unusual: she started as a fourth and fifth grade math teacher, got pulled into SaaS by the learning platform she used in her own classroom, and has since built enablement from scratch at a CRM company and an AI company. Her thesis is deceptively simple. Enabling a seller to sell is not that different from teaching a fourth grader how to divide — the hard part was never the teaching, it was the system around it. In this conversation we get into why enablement is the most misunderstood function in go-to-market, how to actually prove its impact, why she thinks the function belongs under the CRO and not RevOps, and the AI problem that keeps her up at night — which is not slop, it is maintenance. WHAT YOU'LL LEARN Why an ARR number is the wrong trigger for hiring enablement — and the three readiness gates that actually matter How launching MEDDIC at a sales kickoff is roughly 5% of the work, and what the other 95% looks like operationally The classroom "exit slip" and why call recording scorecards are the same instrument in a different room How to build the ROI case for an enablement program before you run it — conservative, medium, and blow-it-out-of-the-water Why Cheyenne thinks enablement reporting into RevOps quietly turns into a helper function How to measure roles that sit far from the revenue line — customer success engineers, applied engineers, SDRs The leading indicators she pulls from call intelligence to know whether a talk track is landing How to find the cracks when nothing is obviously broken and every rep hit quota last year Why AI slop is the wrong thing to worry about, and who owns the pricing calculator when pricing changes The build-versus-buy test she uses — and why she refused to vibe-code an LMS CHAPTERS 00:00 — Cold open and intro 01:47 — From fourth-grade math teacher to GTM enablement 04:55 — Teaching a seller to sell is teaching a kid to divide 06:54 — What's actually under the iceberg 08:45 — Exit slips became call recording scorecards 09:57 — Tailoring enablement across AEs, CS and engineers 12:54 — What actually changes by role, and what doesn't 16:04 — Measuring a product launch across four teams 18:47 — When the launch is over: how to find the cracks 20:50 — What a QBR looks like for a technical buyer 22:11 — Every rep hit quota — and there's still work to do 23:30 — Building the ROI case for an enablement program 25:51 — Where enablement should report, and where it shouldn't 30:17 — When is a company actually ready for enablement 32:00 — The product marketing prerequisite 36:01 — AI in enablement: what's working and what's risky 39:39 — Who owns the tool when the pricing changes 42:24 — Hiring a head of AI enablement 43:20 — Build vs. buy: why she refused to vibe-code an LMS 46:50 — Cost of maintenance as the deciding test 50:01 — Advice for anyone considering enablement ABOUT THE GUEST Cheyenne Griffith leads go-to-market enablement at Deepgram, the voice AI company whose speech-to-text, text-to-speech and voice agent APIs are used by more than 200,000 developers and 1,300 organizations. She started her career teaching fourth and fifth grade math, was recruited into SaaS by the learning management system she used in her own classroom, and moved from customer success into enablement at Imagine Learning before building the function from the ground up at a CRM company and an AI company. ABOUT THE LEANSCALE PODCAST The LeanScale Podcast is where go-to-market operators talk about how revenue actually gets built — the systems, the data, and the decisions underneath the number. Hosted by Anthony Enrico, co-founder of LeanScale. ▶ Learn more: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Cheyenne on LinkedIn KEYWORDS / TAGS sales enablement, go-to-market enablement, GTM enablement, revenue enablement, RevOps, Revenue Operations, sales operations, MEDDIC, MEDDPICC, sales methodology, sales kickoff, SKO, call recording scorecards, conversation intelligence, win rate, quota attainment, product launch enablement, product marketing, founder-led sales, CRO, AI enablement, build vs buy, LMS, Letter AI, Deepgram, voice AI, developer tools, technical QBR, B2B SaaS, LeanScale Podcast HASHTAGS #RevOps #GTM #SalesEnablement #RevenueEnablement #GTMEnablement #AI #VoiceAI #Deepgram #MEDDIC #ProductMarketing #B2BSaaS #CRO #LeanScale #LeanScalePodcast