Head of Customer Success

Hike Medical Co • Boston, MA

51d • Onsite

About The Position

You’ll be Hike’s first Customer Success Leader and first full-time hire fully dedicated to owning the post-sale customer lifecycle. You’ll lead our largest and most complex relationships across employers, healthcare institutions, and major ecosystem partners, making sure they launch successfully, see real outcomes, and grow with us. This role is an opportunity to manage a high-profile portfolio of our most important customers at any time, act as their go-to partner, and build the systems and rhythms that define Customer Success at Hike. This role is perfect for someone who is: Energized by large-scale enterprises and complex, multi-stakeholder engagements Extremely sociable and loves being in the middle of customer conversations Highly organized (ideally the most organized person on their current team) and thrives when there’s a lot at stake You’ll work closely with the leadership team, Sales, Operations, Product, and be a core driver of revenue retention and expansion.

Requirements

• 6–10+ years in Customer Success, Account Management, or client-facing consulting
• Healthcare, employer benefits, MSK, occupational health, or med-device experience
• Experience working with large enterprises and complex programs (e.g., Fortune 100 employers, major health systems, large manufacturers)
• Proven ability to concurrently manage many high-profile accounts in a high-pressure environment
• Track record of driving adoption, renewals, and expansion in an existing book of business
• Exceptionally strong relationship-building and communication skills, from operators to C-suite
• Extremely sociable and comfortable leading customer meetings, workshops, and QBRs
• Highly organized with a strong system for keeping projects, stakeholders, and actions on track
• Experience partnering with Sales, Operations, Product, and Support
• On-site in Boston, five days a week

Nice To Haves

• Background in digital health benefits or tech-enabled physical products
• Experience in venture-backed or high-growth early/growth-stage companies
• Exposure to building or scaling CS processes and tooling (e.g., HubSpot)
• Experience with complex implementations or rollouts across distributed workforces

Responsibilities

• Customer Ownership: Act as the primary point of contact for our key customers to help build deep, trust-based relationships and ensure the success of the partnerships. Manage multiple complex engagements at once with tight project plans, clear communication, and zero dropped balls.
• Onboarding & Launch: Lead end-to-end onboarding and rollout plans, coordinating with internal teams to ensure smooth deployment and strong early adoption.
• Adoption, Outcomes & Renewal: Track and report on statuses of customer relationships and and proactively drive renewal and expansion opportunities.
• Communicate Customer Sentiment Internally: Synthesize and share customer feedback with management team, Product, Operations, and Commercial teams to shape roadmap and focus on continuously improving the experience.
• Systems & Scale: Help build best-in-class playbooks, processes, and reporting that allow Customer Success at Hike to effectively scale with the business.
• Escalation Leadership: Own high-pressure escalations, coordinate cross-functional response, and turn issues into long-term improvements.

Benefits

• Competitive cash compensation + equity
• Full medical, dental, and vision coverage
• $15K relocation bonus if needed
• The opportunity to build Customer Success from the ground up at a category-defining company
• Daily collaboration with the founding team and senior leadership
• Free custom insoles (of course…)

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 11-50 employees