Client Manager - Group Benefits

Your Career Choices Matter: Own your Opportunity and Create a Meaningful Path with Taylor Oswald

Job Summary: Responsible to provide external support to clients for an assigned book of business, giving internal direction to the client management support team; collaborates with internal resources as needed to ensure the client's needs are satisfied with responsibility for retaining existing business.

A Day in The Life:

• Serves as the key service contact to identify, design, communicate and implement cost effective benefit solutions to minimize risk; responds to requests for assistance in a timely and collaborative manner.
• Approximate workload defined by Practice:
  • Large:  6 - 10 accounts; total book value of $1M - $1.5M.
  • Middle Market:  25 - 75 accounts; total book value of $300K - $1M.
  • Small Market:  30 - 44 accounts (efficiencies of scale considered); total book value of $300K - $750K.  

• Works closely and builds relationships with client contacts at the HR leadership and CFO levels.

• Ensures the assigned team maintains the existing client base plus the up-selling and cross selling of other Oswald Products/Services throughout all Oswald market segments.
• Directs the onboarding of new clients, which includes obtaining historical and current information for the building and cataloging of client files in the internal systems; ensures the accuracy of all data and the capturing of commissions.
• Executes support team activities to meet the client's specific needs, which include the creation of the annual service calendar, scheduling meeting times and agenda, and other deliverables to be completed by the established client deadline.
• Works with support staff to ensure all online records are complete and accurate both at the time of renewal and at the point of final information; confirms records are continuously maintained and updated for the accepted lines of coverage.
• Collaborates with the service team on the preparation and peer review of all client deliverables, which are reviewed with Client Executive for final approval and client presentation.

• Conducts open enrollment meeting and ensures all deliverables are accurate including pre-renewal projection, market evaluation and pricing summary, annual renewal, open enrollment materials, annual utilization review, compliance notifications, wellness information, and any other items deemed necessary.
• Prepares and secures commission agreements with carriers, and/or Oswald's fee agreements, monitoring the timely receipt of commission’s receivable following the acceptance of contracts.
• Captures all meeting notes and activities during client-facing sessions and provides information to support staff for processing; meeting notes should clearly outline the action needed and party responsible for the activity and timing.
• Responsible for the final execution and delivery of meeting action items.
• May drive the strategic planning process and collaborate with the Client Executive where applicable to develop and monitor a long-term, integrated and comprehensive health management strategy customized to the client’s needs.
• May develop detailed implementation timelines and plans, ensuring timely client deliverables through effective leadership of small teams.
• Initiates the renewal negotiation process on behalf of the client in collaboration with the Client Executive.  Creates pre-renewal and renewal presentations for Client Executive review.
• Directs the service team in the development of any online, client-specific enrollment portal.
• Trains support staff in the understanding and coordination of key operational activities and processes; develops the skills of team members and their industry knowledge base.
• Understands the details of Healthcare Reform, HIPAA, COBRA and other legislation, which affects the business unit; guides the client in the execution of the appropriate steps to meet regulatory requirements. Validates decisions made by clients meet compliance guidelines as it relates to ACA (affordability, minimum coverage, preventive care, etc.)
• Attains further education, coursework and skills development opportunities to obtain professional designations in their field of expertise.

What You’ll Need:

• A college degree is an advantage but not a requirement
• Life, Health & Accident License required
• At least 3 to 5 years of industry knowledge is required, to include experience in medical benefits and ancillary lines of coverage
• Strong tactical skillset
• General understanding of technical concepts – self-funding, different carriers solutions, etc.
• Strong relationship skills
• Ability to execute
• Self-starter - Ability to work independently with little oversight
• Intuitiveness – knowing when to loop in Client Executive and leadership for escalated issues
• Ability to oversee CSA’s and provide general tactical oversight
• Project management skills – ability to work with internal and external partners to deliver results timely.

Who You Are:

• Energetic with a desire to learn new skills
• Strong organizational skills with ability to transition quickly from one job to another
• Ability to problem solve, think logically and work independently
• Ability to demonstrate a positive attitude and lead by example consistently
• Works well under pressure and meets established deadlines
• Strong verbal and written communication skills
• Strong interpersonal skills with a collaborative approach
• Ability to manage time-sensitive projects
• Ability to guide others in a professional manner and serve as a mentor to subordinates

Who is Taylor Oswald?

Join Taylor Oswald, a minority-owned employee benefits and risk management firm, and you'll do more than just a job – you'll make a real impact. As an MBE-certified partner of Oswald Companies, we offer the resources and reach of a large organization with the close-knit culture and growth opportunities of a small business. We seek to build lasting and trusting client and employee relationships with every interaction, every day.

We're passionate about serving clients, communities and each other.  We believe that diverse perspectives lead to better solutions. If you're looking for a company that invests in its people and fosters a collaborative, supportive environment, Taylor Oswald is the place for you. We offer competitive benefits, professional development opportunities, and the chance to work somewhere special.

What you’ll get?

Make a Difference. Grow Your Career. Every team member at Taylor Oswald lives our INTREPID values: innovation, nimbleness, trust, resourcefulness, excellence, passion, integrity and diversity. No two days are the same, and our team operates collaboratively, making a dynamic environment.

Hybrid schedule with a three-day in-office and two days at home.  We balance work, life, and commuting.

Excellent office locations Cleveland offices relocation to premier space at the Oswald Tower located on the East side of the Flats in Summer 2025!  Updated spaces and amenities are exemplary!  All other regional areas offer updated workspaces at locations in Cincinnati, Detroit, Pittsburgh, and more!

Competitive pay for skills and talents aligned with each role within our organization. We strive for the excellence and retention of our talented team. 

Fantastic Benefits We recognize that taking care of yourself and families are essential.  A wide range, including health and wellness for starters, along with a 401k retirement plan that is far above the standard, a 30-day paid-leave sabbatical after 10 years that comes with a bonus, and so much more.