Head of Customer Success and Implementation

Pear Suite is a mission-driven healthcare technology company transforming how community-based care is delivered. Our platform empowers community health workers, doulas, and other frontline providers with tools to coordinate care, track outcomes, and improve health equity. We partner with organizations serving Medicaid and Medicare populations, delivering social and preventive care at scale.

We're a mission-driven team committed to health equity and innovation in community-based care. You'll thrive here if you're eager to take initiative, value autonomy, and enjoy building structure where none exists. Join us to build scalable, human-centered technology that empowers frontline workers and improves lives across the U.S.

We\'re seeking a Head of Customer Success and Implementation to lead how we deliver, support, and grow our customer partnerships. You will own the full customer journey—from onboarding and implementation to adoption, retention, and expansion. This is both a strategic and hands-on role: you\'ll design scalable processes, lead customer-facing teams, and directly engage with our most important partners to ensure they achieve measurable impact with Pear Suite.

• Lead the Customer Success and Implementation functions, building the strategy, playbooks, and processes for a rapidly scaling healthcare SaaS platform.
• Oversee new customer onboarding and implementation projects, ensuring timely and successful go-lives.
• Drive adoption, engagement, and measurable outcomes across Pear Suite\'s customer base.
• Establish KPIs for retention, expansion, NPS, and time-to-value.
• Serve as executive sponsor for key customers, building strong, trust-based relationships with senior leaders at partner organizations.
• Partner closely with Product, Engineering, and Sales to ensure customer feedback informs roadmap and delivery.
• Build and mentor a high-performing Customer Success and Implementation team, fostering career growth and development.
• Develop scalable processes, tools, and systems to support a growing, diverse customer base.
• Provide regular reporting and insights to the executive team and Board on customer health, retention, and revenue impact.
• Manage escalations and ensure quick, empathetic resolution of customer issues.

• 7+ years of progressive experience in Customer Success, Implementation, or related functions, ideally in SaaS.
• At least 3 years of leadership experience managing customer-facing teams in healthcare or healthtech or community based groups.
• Demonstrated success in scaling customer success/implementation functions in a high-growth startup.
• Strong background in implementation project management, with a proven ability to deliver on time and within scope.
• Deep knowledge of SaaS metrics (retention, NRR, churn, time-to-value, etc.) and how to improve them.
• Experience supporting Medicaid/Medicare-focused organizations, provider groups, or community-based organizations strongly preferred.
• Ability to balance strategic leadership with hands-on execution.
• Exceptional communication skills, with the ability to make complex workflows and data clear to diverse stakeholders.
• Proven ability to build and maintain strong executive-level relationships with customers.
• Comfort navigating ambiguity, creating structure, and driving outcomes in fast-changing environments.
• Experience with CRM, CS, and project management tools (e.g., Salesforce, HubSpot, Gainsight, Asana, etc.).
• MBA, PMP, or similar credentials are a plus.

• The compensation range for this position is $140,000-$180,000
• A mission driven culture that values innovation, collaboration and growth
• Fully Remote
• Unlimited PTO
• Health, dental, and vision insurance
• Health and Wellness Stipend
• Tech Stipend
• Co-working Stipend