Director, Insurance Strategy and Operations at Openly


Title: Director, Insurance Strategy & Operations (Remote)

  • Location: Remote
  • Category: Operations
  • Job Type: Full-Time

Job Desc:

Openly is building a next-generation insurance company from the ground up. We’re paying close attention to the way customers want insurance to work, and questioning the way things have been done in this industry for over a hundred years – everything from how insurance is quoted and sold, to the frustrating back-end operations that waste money. Insurance is filled with interesting engineering problems that need a fresh perspective. You can watch our Techstars 2018 Demo Day video to learn more about what we’re building.

This isn’t something we’ve undertaken on a whim – the founding team brings executive-level experience from Liberty Mutual Insurance and Goldman Sachs, with mastery in actuarial science, computer engineering, math, and finance (MIT, Duke, and the University of Michigan). The rest of the team are key early hires who are experts in their respective fields of statistics, actuarial science, engineering and insurance operations.

We’re backed by a select group of deeply knowledgeable and dedicated investors including Gradient Ventures (Google’s AI fund), Clocktower Technology Ventures, Techstars, and Point Judith Capital.

Job Description

We are hiring a Director of Insurance Strategy & Operations that will focus on the critical initiatives that will transform the Openly operations team into a next-gen organization that disrupts traditional homeowners insurance market. Reporting directly to the Chief Operating Officer, this highly visible role will lead the development, prioritization and implementation of key initiatives across the sales, agent experience, claims and support teams. This role will also lead the operational analytics that identify key opportunities and trends across the organization. The role will begin with a small team and expand as resources are required with analytics, project execution and user experience teams reporting to this director.

Job Details

  • Own prioritization process for Openly’s Operations organization. This includes developing standard intake processes and ROI quantification processes
  • Lead the implementation of all operational initiatives partnering with business leaders and technology team members to ensure that the initiative maximizes its impact
  • Develop KPI dashboards to monitor the impact of each initiative
  • Lead operational analyses that highlight trends and create recommendations to improve results
  • Identify industry trends and market movements that will allow Openly to continue as a cutting edge homeowners insurance operation
  • Develop financial forecasting and planning tools supporting the operations functions
  • Provide a broad end user experience perspective for all critical Openly initiatives including product and technology enhancements
  • Develop and implement standard project management tools, processes and concepts across the operations organization

Key Requirements

  • Has a proven track record of designing, staffing and leading strategic and operational project teams with increasing responsibility
  • Is passionate about leadership, coaching and developing talent
  • Has a track record of identifying, implementing broad, strategic initiatives and projects
  • Has excellent people and project management skills and the ability to communicate and collaborate effectively with people at all levels across the company
  • Has a track record of developing and implementing structured cross functional prioritization processes
  • Has a track record of developing measurement tools that help assess the success/viability of a new initiative
  • Has strong problem-solving skills
  • Is extremely comfortable operating in ambiguity and addressing complex business questions
  • Has extremely strong analytical skills that allow you to structure a business problem, develop hypotheses and use quantitative methods to test these hypotheses
  • Is results-oriented and has strong decision-making skill


  • Competitive salary, equity position in a start-up company
  • Generous medical, dental, vision insurance plans, 401k plus match, FSA benefits
  • Flexible location and remote opportunities
  • Paid Time Off
  • Fun, fast-paced, startup environment

We are committed to continuing to build a diverse and inclusive workplace. We want to encourage all qualified applicants, regardless of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status to apply.

U.S. Citizens, Green Card Holders, and those authorized to work in the U.S. for any employer will be considered.

See all Other Jobs >

Sign up for Daily Remote Job Alerts!

Want Access to 30,000+ More Remote and Flexible Jobs?

More Jobs

More Jobs

Part-time to full-time,
freelance to employee

More Career Fields

More Career Fields

50+ flexible
job categories

More Resources

More Resources

Q&A's, webinars,
career coaching & more

Learn More About Our Premium Service