Head of Customer Success

Job Summary - Head of Customer SuccessLocation: Boston, MAWorkplace type: On-siteJob Type: Full-timeJob Summary:We are seeking an experienced, relationship-driven, and operationally excellent Head of Customer Success to lead our customer partnerships and build the foundational systems that will define how we support clients at scale. As the organization's first full-time Customer Success leader, you will own the entire post-sale lifecycle - from onboarding and launch to adoption, outcomes, renewal, and expansion - across our most strategic, high-value customers.In this role, you will take the lead on managing some of our largest and most complex enterprise relationships, including major employers, healthcare systems, and ecosystem partners. You will serve as their primary advisor, strategic partner, and advocate, ensuring each customer experiences seamless deployment, measurable outcomes, and continued growth with our platform. You will be the person customers trust most, the partner they call first, and the leader who ensures every engagement runs with precision.You'll collaborate closely with our executive team and cross-functional partners in Sales, Operations, Product, and Support to align priorities, solve challenges, elevate the customer experience, and drive long-term value across the customer base. Your work will directly impact retention, expansion, customer satisfaction, and the scalability of the entire customer success function.This is a rare opportunity for someone who thrives in dynamic, high-stake environments, enjoys building deep relationships, and is excited about designing the operational backbone of Customer Success for a fast-growing, category-defining company.What You'll DoOwn & Grow Key Customer RelationshipsServe as the primary point of contact for high-profile enterprise customers with complex, multi-stakeholder environments.Build deep, trust-based relationships with operational leaders, program owners, and C-suite executives.Maintain a pulse on customer sentiment, usage, needs, and risks, ensuring no details fall through the cracks.Lead Customer Onboarding & LaunchManage all aspects of onboarding and rollout, creating detailed project plans to ensure seamless deployments.Coordinate with internal teams to support technical setup, training, communications, and early adoption.Establish strong customer engagement rhythms from day one.Drive Adoption, Outcomes & RenewalsTrack engagement, utilization, and performance metrics across your customer book.Identify opportunities for upsell, expansion, or deeper integration.Ensure customers achieve measurable results that lead to renewal and long-term partnerships.Represent the Voice of the Customer InternallyTranslate insights, feedback, gaps, and opportunities into actionable guidance for Product, Operations, and Leadership.Help shape product roadmap, service improvements, and customer-facing experiences.Build Scalable CS Processes & SystemsDevelop best-in-class playbooks, workflows, health scorecards, communications templates, and reporting structures.Partner with leadership to build a customer success engine capable of scaling with rapid growth.Support selection and optimization of CS tooling (e.g., HubSpot, project management tools).Lead Escalations & High-Stakes IssuesOwn the resolution of critical escalations with professionalism, urgency, and calm under pressure.Coordinate cross-functional responses and convert issues into long-term improvements.What We're Looking ForMust-Have Experience6-10 years in Customer Success, Account Management, or Consulting in client-facing roles.Background in healthcare, employer benefits, MSK, occupational health, med-device, or similar industries.Experience managing large enterprise clients such as Fortune 100 employers, major health systems, or complex distributed teams.Proven track record of driving adoption, renewals, and expansion.Exceptional communication, relationship-building, and presentation skills.Extremely organized with strong project management capabilities.Comfortable working closely with Sales, Operations, Product, and Support teams.Ability to be fully on-site in Boston, MA, five days per week.Nice-to-Have ExperienceBackground in digital health benefits or tech-enabled physical products.Experience in high-growth or venture-backed organizations.Familiarity with scaling CS processes, systems, and tooling.Experience managing complex multi-phase implementations.What You'll GainCompetitive compensation package with equity.Full medical, dental, and vision benefits.$15,000 relocation bonus if moving to Boston.Opportunity to build a Customer Success organization from the ground up.Direct collaboration with founders, executives, and product leaders.A chance to shape the customer experience at a category-leading company.And yes - complimentary custom insoles.

Salary : $100,000 - $125,000