AI-Driven Ops Leader for Wholesale & Specialty

Socket.dev; Chicago (IL); On-site; USD 317,000 - 387,000; Full time

Benefits offered by this job

Health insurance

401(k) with employer match

Employee Stock Purchase Plan

PTO and holidays

Parental leave

Job summary

Markel Group is seeking a Chief Operations Officer for its Wholesale & Specialty Insurance Division in the United States. This senior executive will drive operational excellence, technology enablement, and broker service to achieve targeted ratios and growth, with AI-enabled process improvements and data transparency.

The role demands 10+ years in insurance operations leadership, deep underwriting and IT expertise, and a proven ability to lead large-scale organizational change.

Qualifications

• 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 identifying high-value use cases, governing risk, and scaling AI-enabled workflows.
• Proven track record at a senior leadership level of driving and owning large scale change.
• Strong understanding of insurance business plans and growth strategies.
• Ability to lead and influence senior leadership across multiple functions.

Responsibilities

• Strategic Operations Leadership: own the operating model across regions, underwriting support, service, and workflow; set the AI-enabled future state; lead transformation to improve speed and efficiency.
• Technology, Digital, and Data Ownership: oversee a federated W&S technology org; set IT roadmap; modernize underwriting and automation; ensure data access and analytics support.
• Execution of P&L-Critical Initiatives: improve productivity and broker/underwriter experience; drive digital trading and small-risk automation.
• Governance, Cadence & Leadership: lead operations/IT governance forums; align underwriting, claims, Ops, IT, HR, and finance; prepare quarterly reviews.
• People, Culture & Talent: build a high-performing integrated Ops/IT/Data team; mentor leaders; foster empowerment and continuous improvement.

Skills

AI fluency

Strategic leadership

Underwriting processes

IT systems

Change management

Education

Bachelor’s degree in Business Administration, Insurance, Information Technology, or related field

Tools

Analytics platforms

Enterprise IT

Job description

Markel Group is seeking a Chief Operations Officer for its Wholesale & Specialty Insurance Division in the United States. This senior executive will drive operational excellence, technology enablement, and broker service to achieve targeted ratios and growth, with AI-enabled process improvements and data transparency.

The role demands 10+ years in insurance operations leadership, deep underwriting and IT expertise, and a proven ability to lead large-scale organizational change.