Risk Strategies Company

Team Leader, Senior Director Benefits

Risk Strategies Company  •  Florida (Remote)  •  4 days ago
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Job Description

Built on meritocracy, our unique company culture rewards self-starters who are committed to doing what is best for our customers.

The Team Leader serves as the primary link between internal and external stakeholders, ensuring the effective delivery of products and services. This role provides leadership for the service team, driving client satisfaction through best practices, service coordination, mentoring, and strategic guidance. The Team Leader oversees account management teams, leads complex projects, supports vendor negotiations, resolves client issues, and serves as a senior resource for clients.

The Team Leader directly supervises team members, reviews work for accuracy, manages team capacity, and ensures client deliverables are timely and accurate. The role is also responsible for revenue growth, client expansion within the team’s book of business, identifying cross-sell opportunities across the RSC/Brown & Brown portfolio, and supporting producers in new business development and proposal creation.

The qualified candidate must possess extensive knowledge of employer-sponsored health and welfare plans, including applicable federal and state regulations.

Your Impact:

  • Oversee and manage a team with total revenue of $7M–$9M+ and support the Managing Director with book of business.

  • Demonstrate thought leadership by promoting best practices, driving client expansion, and ensuring EB initiatives are implemented in partnership with national objectives.

  • Serve as a subject matter expert on health and welfare benefits, including medical, dental, vision, life, disability, and voluntary benefits.

  • Drive adoption of consistent processes, products, services, and solutions to enhance client management.

  • Coordinate account service teams to ensure high-quality, consistent client deliverables and service.

  • Develop and implement best practices, including peer review and quality control of client deliverables.

  • Maintain executive-level client relationships and oversee annual stewardship reporting.

  • Build strong relationships with account management teams and clients to ensure successful execution of plans and deliverables.

  • Stay current on carrier products and market developments, ensuring team and client awareness.

  • Partner with regional leadership and Team Leaders to achieve broader Employee Benefits practice goals.

  • Understand and promote RSC/Brown & Brown value-added resources.

  • Evaluate team performance and provide coaching, feedback, career development, and performance reviews.

  • Support new business development through prospecting, value proposition creation, RFP/proposal support, and finalist presentations.

Successful Candidates Will Have:

  • BA/BS preferred.

  • 10+ years of experience in senior employee benefits account management or a consultative role with progressive responsibility.

  • Strong technical expertise in self-funding, stop-loss, and alternative funding strategies, including captives, direct contracting, and reference-based pricing.

  • Demonstrated ability to exceed core practice competencies and mentor junior staff.

  • Client-facing experience within a consulting firm, insurance carrier, or brokerage environment.

  • Ability to collaborate effectively across regional and enterprise-wide employee benefits teams.

  • Strong organizational skills with the ability to manage multiple priorities and deadlines.

  • Commitment to continuous professional development and staying current on industry trends.

  • Excellent presentation and public speaking skills.

  • Advanced critical thinking and problem-solving abilities.

  • Strong attention to detail and proficiency in Microsoft Excel, Word, and PowerPoint.

  • Active Life, Accident, and Health Insurance License required.

Teammate Benefits & Total Well-Being

We go beyond traditional benefits by supporting the total well-being of our teammates:

  • Health Benefits: Medical/Rx, Dental, Vision, Life Insurance, and Disability Insurance

  • Financial Benefits: Employee Stock Purchase Plan (ESPP), 401(k), Student Loan Assistance, and Tuition Reimbursement

  • Mental Health & Wellness: Free mental health and enhanced advocacy services

  • Beyond Benefits: Paid Time Off, Holidays, Preferred Partner Discounts, and more

Benefits may vary by subsidiary, location, eligibility requirements, and enrollment periods.

The Power To Be Yourself

As an Equal Opportunity Employer, we are committed to fostering an inclusive environment comprised of people from all backgrounds, with a variety of experiences and perspectives, guided by our Diversity, Inclusion & Belonging (DIB) motto, “The Power to Be Yourself.”

Brown & Brown, Inc. (NYSE: BRO) is a leading insurance brokerage firm delivering comprehensive and customized insurance solutions and specialization since 1939. With a global presence spanning 700+ locations and a team of approximately 23,000 professionals, we are dedicated to delivering scalable, innovative strategies for our customers at every step of their growth journey. Learn more at BBrown.com.

Brown & Brown, Inc. and our team of companies is an equal opportunity workplace and is committed to ensuring equal employment opportunity without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, Veteran status, or other legally protected characteristics. Learn more about working at Risk Strategies, part of the Brown & Brown team, by visiting https://us.bbrown.com/careers/

Personal information submitted by California applicants in response to a job posting is subject to Risk Strategies' California Job Applicant Privacy Notice

Recruiting Vendor Disclosure Statement

Brown & Brown does not accept unsolicited resumes from external recruiters, recruitment vendors or employment agencies (“Recruiting Vendors”). Recruiting Vendors must have a valid written agreement and receive prior written authorization from an authorized Brown & Brown representative before submitting candidates for any publicly posted role. Any unsolicited resumes submitted to Brown & Brown or its employees become the property of Brown & Brown, and no fees will be paid for such submissions. Additional information regarding this policy can be found on our careers page.

Risk Strategies Company

About Risk Strategies Company

At Risk Strategies, part of the Brown & Brown team, we help our clients protect those things that matter most to them. We help them see the way forward in a complex world with specialty insight, practical advice, and custom insurance with a vast network of specialists in Property & Casualty, Employee Benefits, Private Client, as well as Consulting Services and Financial and Wealth Management solutions.

We are a different kind of insurance brokerage – bringing a strategic, holistic, specialist approach to our clients, so they can face the future with confidence.

We love what we do, and it shows.

For five straight years, we were named one of the Best Places to Work by Business Insurance. In 2025, we earned certification as a Great Place to Work for the second year in a row.

Risk Strategies is an Accession Risk Management Group company, a family of specialty insurance distribution and risk management companies powered by a shared vision of delivering a superior client and employee experience.

Industry
Finance & Insurance
Company Size
1,001-5,000 employees
Headquarters
Boston, MA
Year Founded
1997
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