Director/Sr. Director Chief of Staff, Wholesale & Specialty

Markel • Chicago, IL

5d • $158,000 - $218,000 • Hybrid

About The Position

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 of Staff for the Wholesale & Specialty Division is a critical strategic partner to the President of Wholesale and Specialty. This role is responsible for driving cross-functional initiatives, optimizing organizational performance, and ensuring alignment of division priorities with overall business objectives. The Chief of Staff must be a self-starter who excels in navigating ambiguous environments and thrive when faced with undefined parameters, approaching challenges with creativity, strategic influence and operational excellence.

Requirements

• Bachelor’s degree in Business Administration, Management, Finance, or a related field
• 7+ years of relevant experience in strategic roles, project management, or consulting, ideally within E&S insurance market, or related industries.
• Exceptional problem-solving abilities with a demonstrated capacity to operate effectively in ambiguous and dynamic environments.
• Ability to run multiple efforts, either assigned or self- initiated, simultaneously, prioritize effectively, and maintain a flexible, solutions‑oriented mindset.
• Excellent communication and interpersonal skills, with proven experience influencing and collaborating across all levels of an organization.
• Strategic mindset and a track record of thinking creatively beyond conventional parameters to deliver innovative solutions.
• Strong organizational skills, including the ability to juggle multiple priorities and projects simultaneously.
• Intellectually curious, goals-driven, motivated and a proactive approach
• High emotional intelligence and resilience, able to navigate change and uncertainty with composure and effectiveness.
• Proficiency in analytical tools and technology platforms relevant to strategic planning, process improvement, and reporting.
• US Work Authorization required. Markel does not provide visa sponsorship for this position, now or in the future.

Responsibilities

• Serve as a trusted advisor and right hand to the President, acting as a liaison among senior leaders, teams, and stakeholders.
• Lead and coordinate high-impact projects that often lack pre-defined structure, requiring innovative problem-solving and strategic vision.
• Support the development and adoption of AI initiatives across the division.
• Interpret complex business data and inform with strategic decisions.
• Foster effective communication and facilitate training sessions in collaboration with the leadership team, ensuring alignment and knowledge sharing across the broader division and among diverse stakeholder groups.
• Anticipate and proactively address emerging issues, synthesizing complex information into actionable plans.
• Foster an agile and adaptive team culture by encouraging experimentation, learning, and the pursuit of unconventional solutions.
• Drive strategic planning, manage competing priorities, and ensure effective execution of key initiatives in a fast-paced, dynamic environment.
• Promote and oversee the development of synergies and efficiencies across teams
• Model resilience, resourcefulness, and a collaborative spirit to empower teams and support the division’s long-term success.
• Travel alongside the Wholesale & Specialty President up to 50% of the time during the initial phase in order to gain a deep understanding of the business operations, the specific responsibilities of the role, and the needs of the division.

Benefits

• In keeping with the values of the Markel Style, we strive to support our employees in living their lives to the fullest at home and at work.
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 5,001-10,000 employees