Director Insurance Operations Jobs in Kentucky (NOW HIRING)

Boston, 131 Dartmouth Street, Boston, Massachusetts, United States of America

Norwalk, 50 Washington St, Norwalk, Connecticut, United States of America

West Hartford, 71 Raymond Rd., West Hartford, Connecticut, United States of America

Chicago, 123 N Wacker Dr, Chicago, Illinois, United States of America

New York, 12 E. 49th Street, New York, New York, United States of America

Washington D.C., 655 15th Street Northwest, Washington, District Of Columbia, United States of America

Atlanta, 1 Concourse Pkwy, Atlanta, Georgia, United States of America

United States

Job Description

Posted Monday, August 24, 2026 at 4:00 AM

About the Company

Vantage Group Holdings Ltd. (Vantage) was established in late 2020 as a re/insurance partner designed for the future. Driven by relentless curiosity, our team of trusted experts provides a fresh perspective on our clients’ risks. We add creativity to tech-enabled efficiency and robust analytics to address risks others avoid. Vantage provides specialty re/insurance through its operating subsidiaries in Bermuda and the U.S.

Vantage has approximately 365 colleagues in both the United States and Bermuda. We have offices in Chicago, IL, Norwalk, CT, West Hartford, CT, Washington, DC, Boston, MA, New York, NY, Atlanta, GA and Hamilton, Bermuda. Additionally, we are a highly geographically diverse workforce with colleagues based in 35 states and counting. We fully support work flexibility including remote and hybrid work arrangements.

About the role:

At Vantage, the Head of Insurance Operations will help shape the next stage of our insurance platform. Reporting to the Chief Underwriting Officer, this leader will build the operating discipline, service model, and scalable infrastructure that enable underwriting teams to move faster, serve brokers and clients more effectively, and support continued growth.

This is a high-impact opportunity for an operations leader who understands insurance from the inside out and wants to modernize how work gets done. The right candidate will bring a balance of strategic judgment and hands-on execution: someone who can redesign workflows, lead teams through change, use data to improve performance, and influence senior leaders while staying close to the details that matter.

The base salary expectation for this role is between $220,000 and $275,000. Actual base salary for the selected candidate may be higher commensurate with candidate experience and expectations. Additionally, Vantage offers its colleagues performance-based bonus potential, strong health & welfare benefits, retirement plans with company match, competitive time off plans, a highly flexible work environment, and much more.

Responsibilities & Accountabilities:

Leader of Leaders

• Lead onshore and offshore underwriting operations teams, creating a consistent, high-accountability service model across the insurance business.
• Oversee core underwriting operations workflows, including submission intake, loss runs, policy issuance, endorsements, quality, training, onboarding, analytics, admitted licensing, and NDA processes.
• Develop operating plans, budgets, workforce plans, and capacity models that enable growth, improve service, and support Insurance Leadership Team priorities.

Service Delivery

• Strengthen service delivery for underwriters, brokers, and market partners by improving cycle times, quality, SLAs, and overall operating performance.
• Optimize offshore service performance, work-transfer opportunities, vendor relationships, and related service or technology contracts.
• Oversee assigned operational responsibilities that support a reliable, professional, and scalable operating environment.

Process and Continuous Improvement

• Modernize underwriting workflows from submission intake through issuance by simplifying processes, removing bottlenecks, and freeing underwriting capacity.
• Apply structured continuous improvement methods to standardize, consolidate, or eliminate work while maintaining strong controls and execution discipline.
• Turn process changes into sustained results through clear documentation, training, change management, and impact tracking.

Technology Adoption and AI-Enabled Work Design

• Partner with Technology and Data teams to introduce practical tools, automation, and AI-enabled solutions that improve efficiency while preserving underwriting judgment, quality, and engagement.
• Bring an operations lens to enterprise process and technology planning by defining clear problems, measurable baselines, and priorities tied to business impact.

CUO Support

• Serve as a trusted partner to the CUO, Business Managers, and business leaders on complex compliance, regulatory, technology workflow, data integrity, and client/broker needs.
• Maintain current operational documentation and lead strategic initiatives that help the broader insurance organization scale effectively.

Ideal Candidate Profile:

• Bachelor’s degree preferred or equivalent professional experience.
• CPCU, ARM, or continuous improvement certifications a plus.
• 12-20 years of experience in insurance operations, underwriting operations, or a closely related commercial, specialty, E&S, admitted, or non-admitted insurance environment.
• Travel expected at 20-30%, including Bermuda and offshore partner locations.
• Has led leaders across onshore, offshore, or outsourced teams and is comfortable managing vendor partnerships that are critical to service delivery.
• Knows how to improve complex workflows, measure performance, and translate operational insight into meaningful business outcomes.
• Understands submission clearance, policy administration, underwriting processes, authority frameworks, and documentation standards.
• Can evaluate vendors, service models, digital tools, and AI-enabled capabilities with practical judgment and a clear focus on business value.
• Builds credibility with senior leaders, underwriters, and operations teams, and can lead change across business units.

Our Vantage Values

Do What’s Right – be a force for good, for our customers, shareholders, colleagues, industry and communities.
Be Relentlessly Curious – ask questions, listen to understand, challenge the status quo, look for ways to say YES, drive innovation, be opportunistic and disciplined.
We’re Better Together – collaborate, be inclusive, supportive, respectful and humble, be a trusted partner internally and externally.
Be Transparent – in who you are, what you think, and how you work, seek and provide alternative points of view, be true to yourself.
Make A Difference – focus on impact, embrace technology, leverage data and analytics as critical assets, act intentionally to deliver on our mission.

We value diversity and are committed to creating an inclusive environment for all employees. At Vantage, we strive to build and foster a culture where inclusiveness is ingrained, not just an initiative. All colleagues support building an inclusive environment where employees feel empowered to share their experiences and ideas to foster an environment which encourages you to "Be You!" We are proud to be an equal opportunity employer.

Boston, 131 Dartmouth Street, Boston, Massachusetts, United States of America,

Norwalk, 50 Washington St, Norwalk, Connecticut, United States of America,

West Hartford, 71 Raymond Rd., West Hartford, Connecticut, United States of America,

Chicago, 123 N Wacker Dr, Chicago, Illinois, United States of America,

New York, 12 E. 49th Street, New York, New York, United States of America,

Washington D.C., 655 15th Street Northwest, Washington, District Of Columbia, United States of America,

Atlanta, 1 Concourse Pkwy, Atlanta, Georgia, United States of America,