Customer Success Lead (Benefits Strategy & Administration)
Location: Miami, FL (On-site / Hybrid)
Compensation: $125,000 – $175,000 Base + Renewal Commissions + Equity Options
The Opportunity: Defining the Client Journey
We are representing a high-growth HealthTech/Fintech startup that is fundamentally disrupting the Government Contracting (GovCon) benefits space. While most "Customer Success" roles focus on platform logins and tech engagement, this position is focused on Strategic Administration and Compliance.
Our clients are HR Directors and Executives navigating complex federal regulations (SCA, Davis-Bacon, ICHRA). They don't need a "SaaS cheerleader"—they need a Customer Success Lead who acts as a trusted advisor, handles complex escalations with ease, and builds the operational infrastructure that ensures every group is managed flawlessly.
The Role: Architect of the Success Function
As the Customer Success Lead, you will take the day-to-day client reins from the Co-Founders. You will be responsible for professionalizing the function, creating the templates for daily CS operations, and ensuring that our high-touch administration remains a competitive advantage as we scale.
Key Responsibilities
- Strategic Client Ownership: Act as the lead point of contact for HR Directors. You will handle "annoyed" or high-pressure client situations by providing expert solutions rooted in benefits knowledge.
- Process & Template Creation: You aren't just managing accounts; you are building the department. You will create the SOPs, day-to-day CS templates, and educational resources that standardize our client experience.
- Benefits Administration & Strategy: Manage the full lifecycle of the group—from onboarding and strategy to compliance and the standard enrollment cycles.
- Bridge to Leadership: Partner with the Co-Founders to provide client insights that influence the product roadmap. You own the day-to-day so the founders can focus on high-level subject matter expertise.
- Scalable Growth: Define the metrics for success and build the foundation for what will eventually become a full Customer Success team under your guidance.
Who You Are (The "Ace")
- The Benefits Expert: You have a deep background in Health Benefits, Insurance, or Fringe Benefits. You understand the mechanics of health plans and can speak fluently to HR leaders about their specific pain points.
- The Process Architect: You love creating order out of chaos. You naturally build templates and workflows to make your day-to-day more efficient and repeatable.
- The Resilient Leader: You are comfortable handling tough conversations. You build trust through expertise, empathy, and a "solutions-first" mindset.
- The Startup Operator: You thrive in fast-paced environments where you have the freedom to build from scratch. You are excited to be on-site in Miami, building the company’s "War Room" alongside the founders.
- The "Consultative" Lead: You understand that in this niche, Customer Success is about high-quality execution, compliance, and education—not just "tech engagement."
Qualifications
- Experience: 5+ years in Customer Success, Account Management, or Client Service within Benefits, Insurance, TPA, or GovCon/Fringe Benefits.
- Domain Expertise: Intimate knowledge of the benefits enrollment cycle and the legal/compliance landscape of B2B HR.
- Operational Grit: A track record of creating processes, templates, or playbooks from scratch in an early-stage or high-growth environment.
- Location: Must be in (or willing to relocate to) Miami.
Why Join?
- Direct Financial Upside: A competitive base salary plus commission on renewals, directly rewarding you for the retention of the business.
- Founding Team Access: Work side-by-side with the Co-Founders during a period of explosive growth ($9M+ pipeline).
- Leadership Path: This is the "ground floor" of the CS function. You aren't just a hire; you are the blueprint for the entire department.
- Equity: Significant equity stake in a company solving a multi-billion dollar problem for the American workforce.