Head of Customer Success

Head of Customer Success Job type: Full Time · Department: Operations · Work type: On‑Site San Francisco, California, United States About Fulcrum The $1.5 trillion insurance industry is powered by brokers. Every business needs insurance, and the brokerage industry is hamstrung by account management capacity. Account managers are constantly pulled in multiple directions—keying information into systems, chasing documents, doing mundane work—rather than focusing on the client interactions that actually matter. Most brokerages either outsource this work or grind through it manually. We’re building an AI platform to automate this insurance drudgery. Our platform already saves customers thousands of hours and millions of dollars every year. Our customers love the product— we have deep penetration within enterprise brokerages and genuinely enjoy making our customers’ lives better. We just raised our Series A and are just getting started. Why Fulcrum Rocket-ship growth. We’ve achieved multiple seven figures in ARR in just over a year, serving large enterprise clients including 30% of the top 50 brokers in the country. Extreme ownership. You’ll work directly with enterprise users and ship end‑to‑end products that save them hours every week. Bleeding‑edge problems, real impact. Tackle tough AI and product challenges whose wins show up immediately in customer workflows. In‑person collaboration. Join a lean, staff‑level team (ex‑Affirm, Uber, DoorDash, McKinsey) working side‑by‑side in San Francisco; we believe the best ideas are fostered in an in‑person environment. Top‑of‑market rewards. Competitive base salary plus meaningful founding‑team equity. About the Role As the Head of Customer Success at Fulcrum, you will build and lead the team that turns product potential into undeniable customer outcomes. You’ll own the customer journey end‑to‑end across a complex, highly strategic book of business — from flagship enterprises to scaled accounts — and design the CS org that supports them. You will set the operating model, hire and develop a high‑performing team, run the renewal and expansion engine, and make value unmistakable through granular, workflow‑level adoption instrumentation. This is a ground‑floor opportunity to architect how an entire industry experiences AI‑powered software. Responsibilities CS strategy + operating model: Design and own the customer success strategy for our vertical AI product. Define segmenting, coverage, and service levels that flex with customer complexity (ARR, integrations, multi‑entity rollouts, compliance, workflow breadth) while remaining efficient and scalable. Translate that strategy into clear processes, playbooks, and rituals. Team leadership & org building: Build and scale a high‑caliber CS org. Hire, coach, and develop CSMs and implementation leads (and managers as you grow). Define roles and career paths, set performance standards, and create capacity models that keep the team sustainable while the business scales. Champion a culture of ownership, curiosity, and operational excellence. Retention + renewals: Own GRR and be accountable for renewals across the book. Build a rigorous renewal motion with forecasting, risk identification, and proactive saves. Partner with RevOps and Sales on renewal discipline, deal hygiene, and clear accountability. Expansion + value growth: Co‑own NRR with Sales. Stand up CS‑led expansion plays tied to adoption, outcomes, and executive value narratives. Run structured account planning, identify whitespace, and help customers expand across lines of business, teams, and workflows. Adoption system + instrumentation: Define what “good” looks like by persona and workflow. Set activation, depth, and breadth targets, and build dashboards that make adoption and business impact visible. Implement trigger‑based interventions (alerts, playbooks, outreach) across the lifecycle to move customers from first value → power usage → embedded, must‑have workflows. Enterprise onboarding & rollout: Standardize complex implementations into repeatable, high‑quality playbooks. Orchestrate security and procurement, data readiness, integrations, user provisioning, training, and change management. Ensure that large, multi‑team rollouts land smoothly with clear ownership, milestones, and risks. Customer health, advocacy, and escalations: Own the definition of customer health across product, usage, outcomes, and relationship. Build health scoring that actually predicts risk and opportunity. Lead exec‑level escalations, reset plans, and QBRs / EBRs. Turn successful customers into references, case studies, and design partners. Key success metrics Net Revenue Retention (NRR) and Gross Revenue Retention (GRR) Renewal rate and renewal forecasting accuracy Expansion pipeline influenced and closed Time‑to‑value, onboarding duration, and adoption/usage depth Customer health, NPS/CSAT (where relevant), and referenceability What we offer Competitive salary ($200k-$240k) + meaningful equity. Full health, dental & vision. High‑ownership, high‑trust culture with lightning‑fast executors. Regular team off‑sites, dinners, and an office stocked for builders. #J-18808-Ljbffr