Golden Pear Funding

Head of Customer Success and Implementation

Golden Pear Funding

full-time

Posted on:

Location Type: Remote

Location: Remote • Florida, New Jersey, Oregon, Texas, Washington • 🇺🇸 United States

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Salary

💰 $160,000 - $180,000 per year

Job Level

Lead

Tech Stack

PMP

About the role

  • 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.

Requirements

  • 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.
Benefits
  • 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

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
customer successimplementation project managementSaaS metricsretentionnet revenue retention (NRR)churntime-to-value
Soft skills
leadershipcommunicationrelationship buildingstrategic thinkingproblem-solvingadaptability
Certifications
MBAPMP