Head of Customer Success

Role SummaryOwn the post-sale customer journey end-to-end. Drive revenue expansion via value-led demos and compelling enablement, while lifting adoption, retention, and NPS. Lead CX, Enablement/Training, and Solution Consultants to deliver a consistent, measurable customer experience.Responsibilities:Revenue & UpsellBuild an expansion motion (playbooks, triggers, cadences) with Sales/RevOps.Run executive value reviews and roadmap demos tied to quantified outcomes.Partner with PMM to craft upgrade narratives and pricing/packaging assists.Demos & Solution ConsultingStandardize discovery → demo → business case → close-won handoff.Create demo scripts, reference environments, and ROI calculators.Coach AEs/CSEs on storytelling and objection handling.Training & EnablementOwn customer academy: curricula, certification paths, release trainings.Launch role-based learning (admin, power user, exec) with measurable proficiency.Build scalable content: guides, labs, webinars, in-app tours.Customer Success OperationsDefine health scoring, lifecycle stages, and playbook automation.Stand up QBR/EBR framework and executive sponsorship program.Instrument product adoption dashboards; close the loop with Product on feedback.LeadershipHire, mentor, and performance-manage CX, SC, and Training teams.Forecast headcount/capacity; manage budget and vendor ecosystem.Requirements8–12+ years in Customer Success / Solutions / Enablement; 4+ leading managers.Proven expansion results (upgrade/attach, cross-sell) in B2B SaaS.Expert in discovery, value engineering, and enterprise demos.Built customer education programs (LMS, certifications) at scale.Data-driven operator: lifecycle metrics, cohort analysis, experimentation.Strong executive presence; excellent written and live facilitation skills.Success Metrics (KPIs)Net Revenue Retention (NRR) & Gross Revenue Retention (GRR)Expansion ARR (new ACV from existing accounts), Attach/Adoption ratesTime-to-Value (TTV) and Product Activation benchmarksTraining: course completions, certification rates, CSAT, impact on usageNPS/CSAT, Escalation rate/MTTR, QBR coverageDemo-to-deal conversion (for expansion and new modules)Tooling StackCRM/CS Ops: SalesforceEnablement: Highspot/Seismic, Gong/Wisdom for call librariesTraining: LMS (Docebo/Lessonly), in-app guides (Pendo/Appcues), webinar toolsAnalytics: Looker/Power BI, Product analytics (Amplitude/Mixpanel)30/60/90 Plan30 days: Audit customer journey, segment health, upsell pipeline, demo assets, training catalog. Meet top 20 accounts. Baseline metrics and gaps.60 days: Ship v1 lifecycle playbooks, standardized demo scripts, and a role-based training path. Pilot two expansion plays with A/B measurement.90 days: Roll out academy + certifications, exec QBR framework, and health scoring revamp. Publish CX dashboard; commit quarterly NRR/expansion targets.Team Structure (example)Dir. Customer Success (Segment A/B/C)Sr. Manager, Solution Consulting & DemosSr. Manager, Customer Education & CertificationCS Ops Lead (RevOps dotted line)Interview Prompts (use these)“Walk me through an expansion play you designed—baseline, hypothesis, experiment, lift.”“Show me a demo storyline that moved an upgrade forward—what changed for the buyer?”“How did you tie training completion to product adoption and revenue?”“Describe your health score model—inputs, thresholds, actions.”Nice-to-HavesPublic speaking/webinar chops; conference training sessions deliveredIndustry domain knowledge (your vertical)Experience with multi-product packaging and value metrics