Head of Operation
A privately held organization specializing in employee benefits, insurance, healthcare-related services, and financial services is seeking a Head of Operations to join its leadership team in the San Diego area.
The firm is well-established, founder-led, and operating across multiple regulated business lines. As the organization continues to grow, there is a need for a senior operator who can bring structure, accountability, and execution discipline across a complex, multi-vertical environment.
The Opportunity
Reporting directly to the CEO, the Head of Operations will work closely with executive leadership to build and scale the company's operating infrastructure. This role is designed for a hands-on operational leader who thrives in environments where processes are still being shaped and who wants direct influence over how the business functions day to day.
Rather than stepping into a predefined framework, you'll have significant autonomy to design systems, improve workflows, and align teams across employee benefits, insurance, healthcare, and financial services operations. The role carries a clear progression path to Chief Operating Officer (COO) based on performance and impact.
Key Responsibilities
- Act as a strategic and operational partner to the CEO
- Build and implement scalable operational processes across multiple business lines
- Drive accountability through KPIs, reporting, and performance management
- Improve cross-functional execution across insurance, benefits, healthcare, and financial services teams
- Identify inefficiencies and lead process improvement initiatives
- Support growth initiatives by translating strategy into operational execution
Ideal Background
- Senior operations experience within employee benefits, insurance, healthcare services, financial services, consulting, or similarly regulated environments
- Proven ability to build operational structure in growing or founder-led organizations
- Comfortable operating in ambiguity and creating order as the business scales
- Strong communicator with executive-level presence
- Motivated by long-term leadership opportunity and increasing scope
Additional Details
- Fully on-site role based in the San Diego area, 5 days per week
- Competitive compensation package commensurate with experience
- High-visibility role with meaningful influence and autonomy
This position is best suited for an operations leader who enjoys building the backbone of an organization and is excited by the opportunity to grow into a top executive role alongside the CEO.
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