About Zorro:
Zorro is a rapidly expanding, cutting-edge technology startup revolutionizing how companies deliver employee benefits. Founded by repeat entrepreneurs and supported by a brilliant and growing team, our mission is to build the end-to-end financial platform for healthcare — a system that personalizes benefits for every individual, streamlines costs for employers, and ensures the entire experience works in people’s favor.
We specialize in the Individual Coverage Health Reimbursement Arrangement (”ICHRA”), a transformative new benefit that replaces old one-size-fits-all group health plans. With ICHRA, employers provide tax-free funds, and employees get to choose the health insurance that's right for them.
Zorro's platform makes this new freedom simple. We guide employees through the entire process, helping them fully understand their needs, get the best coverage for them and their families, and smartly take care of their health-related finances. This flips the old benefits model on its head, putting control and personalization at the center of healthcare. With the most advanced platform in the industry, Zorro supports the end-to-end ICHRA journey, enabling the true customization of benefits at scale.
Beyond the technology, we are intentional about the environment we’re building. Zorro is proud to be one of Modern Healthcare’s Best Places to Work in Healthcare, a recognition that reflects our commitment to a culture where Zorriers can collaborate, grow, and solve the industry's most complex challenges together.
Who we’re looking for:
We’re looking for a Director of ICHRA Implementation & Onboarding to build, scale, and lead Zorro’s implementation function as we continue rapid growth in the ICHRA market. This role is responsible for delivering a best-in-class onboarding experience for employers, brokers, and employees — from contract signature through go-live — while creating the processes, systems, and operating model needed to scale efficiently.
You will:
Own the end-to-end ICHRA implementation and onboarding experience, ensuring employers and brokers are set up for success from kickoff through go-live.
Build and scale the Implementation team, including hiring models, capacity planning, and role specialization to support rapid client growth and seasonal enrollment spikes.
Define and standardize implementation processes, documentation, and playbooks to ensure consistent, repeatable, and high-quality onboarding across all client segments.
Own payroll and HRIS integrations during implementation, including:
- Intake and validation of payroll data
- Coordination of integrations (e.g., Finch, direct payroll connections)
- Clear ownership of timelines, dependencies, and issue resolution
- Partnering closely with Product and Engineering on integration requirements and improvements
Design and own the client communication journey during onboarding, including:
- Implementation timelines and expectations
- Employer and broker touchpoints
- Employee-facing education and enrollment communications
- Trigger-based messaging tied to onboarding milestones
Collaborate closely with the Customer Success team to ensure a seamless handoff post-go-live, with clear documentation, context, and risk awareness.
Establish and monitor implementation metrics, including time-to-launch, onboarding completion rates, integration readiness, and client satisfaction during onboarding.
Continuously evaluate and improve tooling and systems used during implementation, identifying opportunities for automation and efficiency gains.
Partner with Product, Engineering, Compliance, and Operations to ensure implementation workflows align with platform capabilities, regulatory requirements, and future roadmap priorities.
Anticipate and mitigate onboarding risks, solving root-cause issues and refining processes to prevent recurring problems.
Serve as an escalation point during implementation, providing executive oversight for complex or sensitive employer and broker situations.
Ensure strong product and ICHRA knowledge across the Implementation team, with a focus on ongoing training, enablement, and readiness ahead of peak enrollment periods.
Who You Are:
- A hands-on operator and builder who has personally owned complex benefits or ICHRA implementations — not just overseen them.
- Comfortable working “in the weeds” when needed, especially around payroll data, eligibility logic, integrations, and enrollment readiness.
- Deeply knowledgeable in ICHRA mechanics, individual market enrollment, SEPs, and broker-led implementation models, with a strong instinct for where things commonly break.
- Experienced in improving implementation functions, driving for efficiencies, including processes, playbooks, tooling, and team structure.
- Execution-first leader who sets the standard through action, not delegation, and expects operational rigor across the team.
- Systems-minded and tech-fluent, able to evaluate, adopt, and improve platforms, integrations, and internal tools to scale onboarding efficiently.
- Confident serving as an escalation owner for complex employer, broker, or employee situations during implementation.
- Thrives in startup environments, adapting quickly, making decisions with imperfect information, and maintaining quality under pressure.
Background & Qualifications
- Bachelor’s degree required.
- 7+ years of experience in ICHRA, individual health benefits, benefits administration, or closely related domains.
- Direct, hands-on experience implementing ICHRA programs for employers is strongly preferred and will be weighted heavily.
- Demonstrated experience owning end-to-end implementations, from contract signature through go-live, across multiple employer groups.
- Prior experience building or scaling an implementation or onboarding team, including capacity planning and operational design.
- Strong working knowledge of health insurance operations, including eligibility, SEPs, enrollment timing, carrier interactions, and payroll or HRIS integrations.
- Proven ability to partner cross-functionally with Product, Engineering, Compliance, and Operations while maintaining execution ownership.
- Experience in high-growth or startup environments strongly preferred; comfort operating through peak enrollment cycles required.
Why join Zorro?
- Disruptive mission: Be part of a team reinventing a trillion-dollar industry.
- High impact: Your work will power critical decisions for thousands of employees and their employers.
- Elite team: Work with repeat entrepreneurs and a group of no-ego, high-horsepower builders driven to create a new benefits paradigm.
- Grow with us: Great opportunity to grow with the team and company as we scale.