Sr. Director, IT Operations, Wholesale and Specialty

Location: Rosemont IL

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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 Senior Director, IT Operations is responsible for the technology strategy, operational performance, and business-aligned delivery supporting Wholesale & Specialty. This leader oversees technology operations for the Wholesale business, leads a small team of developers, and serves as a trusted bridge between business leaders, operational teams, and technical delivery resources. The role translates business needs into practical, scalable solutions that improve service quality, cost effectiveness, employee productivity, and business outcomes.

As a technology and AI champion, the Senior Director accelerates the responsible adoption of artificial intelligence, automation, Microsoft 365, Power Platform, and Python-based solutions. The role identifies high-value opportunities, guides rapid development of fit-for-purpose tools and agents, and ensures solutions are implemented with appropriate governance, security, and controls.

Key Responsibilities

• Own and advance the technology strategy and associated systems supporting Wholesale & Specialty, aligning priorities with business strategy, enterprise technology direction, and operational needs.
• Oversee IT operations and technology-enabled support for the Wholesale business, ensuring reliable, responsive, and effective service delivery.
• Lead, develop, and retain a small developer team responsible for delivering business applications, automations, integrations, and targeted operational solutions.
• Serve as the primary bridge between business stakeholders and developers by translating the Wholesale operating model, workflows, and pain points into clear solution requirements and delivery priorities.
• Champion practical and responsible adoption of AI across the business, helping leaders and employees identify appropriate use cases and embed new capabilities into day-to-day work.
• Lead automation efforts beyond the traditional IT organization, with particular focus on smaller, high-impact solutions that improve front-line processes and can be delivered quickly.
• Oversee the design and delivery of solutions using Python, Microsoft 365, Power Platform, and related enterprise tools, including automated policy and workflow solutions and lightweight AI agents.
• Create an intake and prioritization approach for automation and AI opportunities, balancing speed, business value, scalability, risk, supportability, and available capacity.
• Partner with senior business leadership and enterprise IT to approve, prioritize, and govern the selection, acquisition, development, and implementation of technology solutions.
• Proactively identify opportunities for change across the division, particularly where technology, data, AI, or automation can simplify work, improve controls, or enable growth.
• Ensure continuous and satisfactory delivery of IT services through clear service expectations, performance measures, and effective partnership with the broader IT organization.
• Define and communicate plans, policies, standards, and operating practices for the acquisition, implementation, support, and use of technology solutions.
• Ensure technology activity complies with enterprise governance, cybersecurity, data protection, architecture, legal, regulatory, and control requirements.
• Implement and maintain controls and procedures that protect information systems and data from unauthorized access, modification, disclosure, loss, or destruction.
• Develop and manage the annual technology budget for the supported business, tracking investment, operating costs, value realization, and alignment with approved priorities.
• Participate in strategic and operational governance forums and provide clear recommendations, risk perspectives, progress updates, and decision support to senior leaders.
• Build strong relationships with business, technology, operations, data, risk, and vendor partners to deliver integrated outcomes and resolve complex issues.
• Lead workforce planning, recruitment, goal setting, coaching, performance enablement, succession planning, and professional development for managed staff in accordance with company policies and budget.

Additional Locations: Chicago IL