Head of Customer Success and Implementation

About the role

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.

What you'll do

• 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.

Qualifications

• 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.
  
  

What we offer

• The compensation range for this position is $160,000-$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