Chief Operations Officer, Wholesale & Specialty
Markel
- Location
- Chicago, IL
- Employment
- Full Time
- Work model
- On-Site
- Level
- Staff
- H-1B history
- 1 approvals (FY2023)
- Posted
- Sep 21, 2026
About this role
What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs.

Join us and play your part in something special!

The Chief Operations Officer (COO) for the Wholesale & Specialty Insurance Division is a senior executive accountable for the operational, technological, and executional performance of the US Wholesale & Specialty division — driving underwriting productivity, technology enablement, operational excellence, and broker service to deliver targeted combined ratio and growth outcomes.
Job Responsibilities
Strategic Operations Leadership Own the W&S operating model across regions, underwriting support, service, and workflow Set the vision for the future W&S operating model, articulating a progressive, AI enabled end-state and the path to achieve it Lead transformation initiatives that improve speed, quality, and expense ratio Drive organizational clarity, decision rights, and process consistency Technology, Digital, and Data Ownership Oversee a federated W&S technology organization aligned to business priorities Set and own the W&S IT roadmap in partnership with enterprise architecture Lead modernization of underwriting, workflow, portals, and automation (including AI) Ensure data accessibility, MI/analytics support, and performance transparency Provide transparency on allocations/chargebacks and clearly articulate the value and outcomes delivered by any remaining central operations Execution of P&L-Critical Initiatives Improve underwriting productivity (referrals, cycle times, low-touch workflows) Enhance ease of doing business for brokers and underwriters Drive implementation of digital trading and small-risks automation Improve operational SLAs and service outcomes Governance, Cadence & Leadership Lead W&S Ops leadership meetings; co-own IT & Ops prioritization forums Drive alignment across underwriting, claims, Ops, IT, HR, and finance Ensure effective preparation for quarterly business reviews, regional P&L, and reserving meetings People, Culture & Talent Build a high-performing integrated Ops/IT/Data organization Mentor and develop operational and technology leaders Promote a culture of empowerment, speed, and continuous improvement Education Bachelor’s degree in Business Administration, Insurance, Information Technology, or a related field Work Experience/Skill Set 10+ years of progressive leadership experience in insurance operations, with a focus on wholesale and specialty insurance Demonstrated expertise in underwriting processes and IT systems Demonstrated AI fluency, including the ability to identify high-value use cases, govern risk, and scale AI-enabled workflows across operations and underwriting Have a proven track record at a senior leadership level of driving and owning large scale change. Possess an excellent understanding of all aspects of our insurance business plans and growth aspirations Stay ahead of external trends and ensure creativity and innovation across all aspects of our operations Be confident in leading and influencing senior leadership teams from across the organization, along with managing multiple stakeholder groups at all levels Proven experience of driving process efficiency and an ability to define process excellence Have an ability to coach, mentor and inspire, both within direct team structure and across the organization US Work Authorization US Work Authorization required. Markel does not provide visa sponsorship for this position, now or in the future. Pay information: The base salary offered for the successful candidate will be based on compensable factors such as job-relevant