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

Sorry, this job was removed at 08:16 p.m. (UTC) on Monday, May 18, 2026
4 Locations
In-Office
Insurance
The 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 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.

Job 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.

Education

  • Bachelor’s degree in Business Administration, Management, Finance, or a related field

Work Experience/Skill Set

  • 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.

#LI-Hybrid

#LI-SY

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 Director/Sr. Director Chief of Staff, Wholesale & Specialty is $158,000 - $218,000 with 55% incentive.

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: 

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.   

 

Are you ready to play your part? 

Choose ‘Apply Now’ to fill out our short application, so that we can find out more about you. 

 

Caution: Employment scams 

Markel is aware of employment-related scams where scammers will impersonate recruiters by sending fake job offers to those actively seeking employment in order to steal personal information. Frequently, the scammer will reach out to individuals who have posted their resume online. These "job offers" include convincing offer letters and frequently ask for confidential personal information. Therefore, for your safety, please note that: 

  • All legitimate job postings with Markel will be posted on Markel Careers. No other URL should be trusted for job postings.

  • All legitimate communications with Markel recruiters will come from Markel.com email addresses. 

 

We would also ask that you please report any job employment scams related to Markel to [email protected]. 

 

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 the [email protected].    

No agencies please.

Markel Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Markel and has not been reviewed or approved by Markel.

  • Healthcare Strength Comprehensive coverage includes medical, prescription, dental, vision, and telehealth, complemented by company-sponsored wellness programs and free fitness/mindfulness apps. Feedback suggests expanded mental-health resources and wellness incentives further enhance support.
  • Retirement Support Retirement offerings include 401(k) and other financial protections that can add meaningful long-term value. Feedback suggests strong company matching and retirement contributions are a notable part of the package.
  • Leave & Time Off Breadth A broad suite includes paid time off, corporate holidays, parental leave, hybrid work, volunteer time, and education support. Feedback suggests PTO accrual grows with tenure and can include an option to buy extra days.

Markel Insights

Similar Jobs

Comcast Logo Comcast

Account Executive

Digital Media • Information Technology • News + Entertainment
Hybrid
Sugar Land, TX, USA
115000 Employees

Comcast Logo Comcast

Enterprise Account Executive

Digital Media • Information Technology • News + Entertainment
Hybrid
Houston, TX, USA
115000 Employees

Comcast Logo Comcast

Account Executive

Digital Media • Information Technology • News + Entertainment
Hybrid
Houston, TX, USA
115000 Employees
54K-84K Annually

Cox Enterprises Logo Cox Enterprises

Principal Architect

Artificial Intelligence • Automotive • Greentech • Information Technology • Machine Learning • Software • Cybersecurity
Hybrid
Austin, TX, USA
30000 Employees
163K-272K Annually
Get Personalized Job Insights.
Our AI-powered fit analysis compares your resume with a job listing so you know if your skills & experience align.

The Company
HQ: Glen Allen, VA
3,519 Employees
Year Founded: 1930

What We Do

At Markel, we believe in hard work, a zealous pursuit of excellence, and fairness in all our dealings. Markel Corporation (NYSE: MKL) is a global Fortune 500 company headquartered in Richmond, Virginia. We seek to be a leader in each of our pursuits, with insurance being our primary business. As a market leader for specialty insurance, reinsurance, and investment operations around the world, Markel embodies integrity, commitment, teamwork, and innovation in every day operations. We are encouraged to look for a better way to do things. Since our founding in 1930, we have sought to know our customers’ needs and to provide quality products and service. Markel specializes in providing coverage for hard-to-place risks for a variety of niche markets including: • Agricultural and equine risks • Reinsurance for large risk enterprises such as oil rigs • Event cancellation insurance for weddings, concerts, and sporting events • Inland marine coverage for fine art collections • Environmental pollution • Yachts, ATVs, and motorcycles At Markel we provide an atmosphere in which people can reach their personal potential. We are results-oriented, and we continually strive for a better way to do things. The Markel approach is one of spontaneity and flexibility. Markel helps employees balance work and social activities. Markel gives you the keys to success! Keeping an open mind and learning new skills allows our associates to stay ahead of the marketplace. Above all, we enjoy what we are doing. There is excitement here that comes from innovating, creating, striving for a better way, sharing success with others…winning. That is the Markel Style.

Similar Companies Hiring

Globe Life Thumbnail
Insurance • Financial Services
McKinney, TX
3000 Employees
MassMutual India Thumbnail
Big Data • Fintech • Information Technology • Insurance • Financial Services
Hyderabad, Telangana
Granted Thumbnail
Artificial Intelligence • Healthtech • Insurance • Mobile • Financial Services
New York, New York
23 Employees

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account