Stonehaven - Director of Program Operations

Ledgebrook
•$150,000 - $250,000•Remote

About The Position

At Ledgebrook, we’re building a next-generation insurance infrastructure - fast, smart, and scalable - and are looking for a Director of Program Operations to join Stonehaven Specialty Insurance Company, Ledgebrook’s new third-party hybrid fronting carrier. This role reports to the Chief Programs Officer (CPO) and owns program operations discipline and execution across the full program book, setting the onboarding/offboarding playbook and governance cadence, and supervising the Program Operations Manager(s) who project-manage individual programs day to day. Stonehaven is seeking a Director of Program Operations to own the repeatable program onboarding/offboarding playbook, set the governance cadence for live programs, and supervise the Program Operations Manager(s) who project-manage individual programs day to day. The successful candidate will bring program/project management experience in insurance operations with a track record building multi-workstream onboarding processes and managing a portfolio of concurrent program relationships.

Requirements

  • 8+ years of program/project management experience in insurance operations, including 3+ years supervising a team, ideally in an MGA-oversight or program-fronting environment.
  • Direct experience building or running a repeatable multi-workstream onboarding process spanning underwriting, claims, compliance, and finance.
  • Experience managing a portfolio of concurrent program relationships, not just a single program.

Nice To Haves

  • PMP or equivalent project/program management certification.
  • Prior fronting-carrier or program-administrator-side operations leadership experience.
  • Familiarity with bordereau data flows and DUA audit processes.

Responsibilities

  • Own and continuously improve the repeatable program onboarding and offboarding/runoff playbook (capacity, licensing, data feeds, collateral, claims/TPA setup) used by the Program Operations Manager(s).
  • Supervise and develop the Program Operations Manager(s); review program due-diligence coordination and DUA audit findings across the book.
  • Set the governance cadence for live programs (status meetings, escalation paths) and ensure it is followed consistently across all Program Operations Managers.
  • Escalate cross-functional blockers (Underwriting, Legal, Compliance, Reinsurance, Finance, Technology) that a Program Operations Manager cannot clear alone.
  • Report portfolio-level program-operations health (onboarding pipeline, audit remediation status, runoff status) to the CPO.

Benefits

  • Full remote flexibility and asynchronous work culture.
  • Unlimited PTO and fully paid sick leave.
  • Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options.
  • Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage.
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