Head of Customer Success

Role Summary

Own 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 & Upsell

• Build 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 Consulting

• Standardize discovery → demo → business case → close-won handoff.
• Create demo scripts, reference environments, and ROI calculators.
• Coach AEs/CSEs on storytelling and objection handling.

Training & Enablement

• Own 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 Operations

• Define 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.

Leadership

• Hire, mentor, and performance-manage CX, SC, and Training teams.
• Forecast headcount/capacity; manage budget and vendor ecosystem.

Requirements

• 8–12 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 rates
• Time-to-Value (TTV) and Product Activation benchmarks
• Training: course completions, certification rates, CSAT, impact on usage
• NPS/CSAT, Escalation rate/MTTR, QBR coverage
• Demo-to-deal conversion (for expansion and new modules)

Tooling Stack

• CRM/CS Ops: Salesforce
• Enablement: Highspot/Seismic, Gong/Wisdom for call libraries
• Training: LMS (Docebo/Lessonly), in-app guides (Pendo/Appcues), webinar tools
• Analytics: Looker/Power BI, Product analytics (Amplitude/Mixpanel)

30/60/90 Plan

• 30 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 & Demos
• Sr. Manager, Customer Education & Certification
• CS 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-Haves

• Public speaking/webinar chops; conference training sessions delivered
• Industry domain knowledge (your vertical)
• Experience with multi-product packaging and value metrics