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VP of Sales - Employee Benefits

Ryan Specialty
Chicago, IL; Remote (Indiana); Remote (Wisconsin); Remote (Illinois) Posted Aug 19, 2026
HybridUSD 120,000 - 150,000 / year

About this role

Position Summary

The VP of Sales – Employee Benefits is responsible for commanding territory performance and exceeding targets, through a culture of efficiency and innovation. The role collaborates across the enterprise to grow the benefits business. They shape industry discussions, ensure unwavering compliance with regulations, mitigate potential challenges and maximize profitability.

What will your job entail?

Position Summary:

The VP of Sales – Employee Benefits is responsible for commanding territory performance and exceeding targets, through a culture of efficiency and innovation. The role collaborates across the enterprise to grow the benefits business. They shape industry discussions, ensure unwavering compliance with regulations, mitigate potential challenges and maximize profitability.

Location

Remote or Hybrid (based on location)

Position Responsibilities:

  • Develops and executes strategic vision and direction for the offices across Benefits and Underwriting businesses. Provides strategic leadership and defines business strategies to achieve growth targets and profitability.
  • Spearheads expansion and diversification initiatives and identifies new market segments and product opportunities.
  • Analyzes industry trends, competitor landscape, and regulatory changes, translating insights into actionable strategies.
  • Cultivates a results-oriented culture, fostering collaboration, innovation, and continuous improvement.
  • Assesses regional market trends and competitor strategies, translating insights into actionable plans for growth and market share dominance.
  • Champions Ryan Specialty's brand and value proposition to brokers, manages general agents (MGA) and secures lucrative partnerships and distribution channels.
  • Achieves annual budgeted growth and retention targets.
  • Contributes to industry discussions and initiatives, represents Ryan Specialty's interests and builds strong relationships with key stakeholders.

Work Experience:

Minimum of 7+ years of work experience in Commercial Insurance coverages and Employee Benefit Sales

Education

  • Bachelor’s degree required

Licenses & Certifications:

  • Prescribed: Minimum requirements for state A&H and/or benefits licenses

  • How We Support Our Teammates

  • Ryan Specialty seeks to offer our employees a comprehensive and best-in-class benefits package that helps them — and their family members — achieve their physical, financial, and emotional well-being goals. In addition to paid time off for company holidays, vacation, sick and personal days, Ryan offers paid parental leave, mental health services and more.

  • The target salary range for this position is $120,000.00 - $150,000.00 annually.

  • The wage range for this role considers many factors, such as training, transferable skills, work experience, licensure and certification, business needs, and market demands. The pay range is subject to change and may be modified in the future. Full-time roles are eligible for bonuses and benefits. For additional information on Ryan Specialty Total Rewards, visit our website.

  • We provide individuals with disabilities reasonable accommodations to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment in accordance with applicable law. Please contact us to request an accommodation.

  • The above is intended to describe this job's general requirements. It is not to be construed as an exhaustive statement of duties, responsibilities, or physical requirements. Nothing in this job description restricts management's right to assign or reassign duties and responsibilities to this job at any time. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.

  • Your Career. Our Specialty. Innovation Begins with You.

  • A multi-time winner of Newsweek’s Most Loved Workplaces and Insurance Business’s Top Insurance Employers, Ryan Specialty is home to some of the brightest talent in the insurance industry. Join our team and help provide innovative solutions for insurance brokers, agents and carriers.

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Benefits

  • Curious about Ryan Specialty’s benefits? Explore our employee benefits here!

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  • Ryan Specialty, LLC and its affiliates (“Ryan Specialty”) do not accept unsolicited resumes or candidate profiles submitted by any staffing agencies, placement services or professional recruiters (“Agencies”), including any submissions made through our website or to email accounts of Ryan Specialty employees. Agencies must be registered in Ryan Specialty’s agency portal and have a fully executed contract for service between Ryan Specialty and the Agency.

  • Agency fee agreements will only be valid if provided in such fully executed contract between Ryan Specialty and the Agency. Any unsolicited resume or candidate profile received from an Agency without prior approval from Ryan Specialty’s HR department and in compliance with Ryan Specialty’s candidate submission process shall be considered unsolicited, gratuitous and property of Ryan Specialty for recruiting purposes and, as such, is not subject to payment of any Agency fees.

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  • © 2026 Workday, Inc. All rights reserved.

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