Stonehaven - Director of Program Operations

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.

About the Role

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.

What You'll Do:

• 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.

About you

We love working with people who are eager to learn constantly and genuinely excited about the chaotic, rewarding process of building a company from the ground up.

You’ll be a great fit if you bring:

• A Strong Moral Compass: You believe in doing the right thing, period. We have a strict zero-tolerance policy for toxic behaviors.
• Customer-First Empathy: You are passionate about delivering an exceptional experience to everyone you work with, both inside and outside the company.
• Intellectual Curiosity: You naturally question the status quo and love finding innovative ways to solve problems.
• A Growth Mindset: You possess a hunger for continuous learning and want to constantly expand your skillset.
• Urgency & Prioritization: You can pivot quickly and balance the need to get things right with the speed of getting them done right now.
• A Solution-Oriented Outlook: When things go wrong, you don't look for blame—you immediately focus on how to fix it.
• Transparent Communication: You value honesty, clarity, and open feedback.
• Team-First Energy: You want to win together as a high-performing team and actively build connections across our remote locations.

Requirements

Must Haves:

• 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.

Benefits

US 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.

Compensation

Compensation:

• The base salary range for this position is $150,000-250,000.  This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting.  Actual compensation may vary based on a variety of relevant factors including but not limited to experience, qualifications and geographic location.
• Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.

For Candidates Applying From The U.S.:

Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization.  We are unable to offer sponsorship at this time.

Ledgebrook may use Artificial Intelligence (“AI”) as part of the job application process, including to assist us in evaluating your application.  AI is used as a support tool, and hiring decisions are made by human recruiters. By submitting your information, you acknowledge that the company may use AI tools as part of our evaluation. If you need a reasonable accommodation or alternative review process because of a disability or other legally protected basis, contact hiring@ledgebrook.com. Requesting an accommodation will not negatively affect your application.