Chief Operations Officer, 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

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 education, job-relevant experience, training, licensure, demonstrated competencies, geographic location, and other factors.Title and salary will be commensurate with skill set/experience. The national average salary for the Chief Operations Officer, Wholesale & Specialty is $317,000 - $387,000 with 65% incentive and 35% LTI.

Who we are:

Markel Group (NYSE – MKL) a fortune 500 company with over 60 offices in 20+ countries, is a holding company for insurance, reinsurance, specialist advisory and investment operations around the world.

We’re all about people | We win together | We strive for better

We enjoy the everyday | We think further

What’s in it for you:

• We offer competitive benefit programs that help meet our diverse and changing environment as well as support our employees’ needs at all stages of life.

• All full-time employees have the option to select from multiple health, dental and vision insurance plan options and optional life, disability, and AD&D insurance.

• We also offer a 401(k) with employer match contributions, an Employee Stock Purchase Plan, PTO, corporate holidays and floating holidays, parental leave.

Markel is an equal opportunity employer. We do not discriminate or allow discrimination on the basis of any protected characteristic. This includes race; color; sex; religion; creed; national origin or place of birth; ancestry; age; disability; affectional or sexual orientation; gender expression or identity; genetic information, sickle cell trait, or atypical hereditary cellular or blood trait; refusal to submit to genetic tests or make genetic test results available; medical condition; citizenship status; pregnancy, childbirth, or related medical conditions; marital status, civil union status, domestic partnership status, familial status, or family responsibilities; military or veteran status, including unfavorable discharge from military service; personal appearance, height, or weight; matriculation or political affiliation; expunged juvenile records; arrest and court records where prohibited by applicable law; status as a victim of domestic or sexual violence; public assistance status; order of protection status; status as a smoker or nonsmoker; membership or activity in local commissions; the use or nonuse of lawful products off employer premises during non-work hours; declining to attend meetings or participate in communications about religious or political matters; or any other classification protected by applicable law.

Should you require any accommodation through the application process, please send an e-mail to [e-mail].