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, , | Oswald Companies | Full-time | Partially remote
Senior Client Manager — Captives
Job Summary
The Captive Senior Client Manager provides external service and consulting support to clients for an assigned book of business, offering internal guidance to the client management support team to ensure client needs are met and existing business is retained. Through analysis of client data and performance, along with educational efforts on regulatory and benefit matters, the focus is on delivering cost-effective solutions that minimize risks and foster long-term client relationships in medical stop-loss captives.
A Day in the Life
• Serves as the key service contact for all ISBC retail clients — identifying, designing, communicating, and implementing cost-effective benefit solutions to minimize risk; responds to requests for assistance promptly and collaboratively.
• Builds and maintains client relationships through proactive service, educating clients on plan options, trends, and regulatory matters to enhance satisfaction and support retention; works closely with HR leadership and CFO-level contacts.
• Owns support activities such as creating annual service calendars, scheduling meetings and agendas, and preparing deliverables to meet established client deadlines.
• Provides ongoing consulting support by analyzing claims experience, demographics, plan design, and risk to monitor group performance and proactively address emerging issues such as high-cost claimants or utilization trends.
• Manages day-to-day liaison with carriers, TPAs, and networks — coordinating handoffs, reviewing agreements, and triaging service issues to ensure smooth operations and client satisfaction.
• Manages workflow between wholesale broker partners and the core Captives department, acting as the primary liaison for resources, delegation, and escalations to the Captive Department Head.
• Manages complex service requests requiring multi-department coordination by acting as the primary contact for analytics, compliance, legal, and IT teams, routing requests and collaborating on operational items.
• Refines operational processes, develops service playbooks and templates, and monitors risk trends to enhance efficiency and client loyalty.
• Proactively reaches out to groups with emerging claim issues or administrative problems; identifies up-selling and cross-selling opportunities to strengthen client ties and promote retention across the business portfolio.
• Collaborates with the Client Executive in strategic meetings — including QBRs, pre-renewal, renewal, and post-renewal reviews — to provide insights and co-present on client-focused strategies.
• Collaborates with the service team on the preparation and peer review of all client deliverables for Client Executive final approval; conducts open enrollment meetings and ensures accuracy of pre-renewal projections, market evaluations, pricing summaries, utilization reviews, compliance notifications, and wellness materials.
• 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 onboarding of new clients and handles post-renewal activities, using analysis and consulting to build long-term value; develops detailed implementation timelines and plans to ensure timely delivery through effective leadership of small teams.
• Works with support staff to ensure all online records are complete and accurate at renewal and at the point of final information; confirms records are continuously maintained and updated for accepted lines of coverage.
• Trains and mentors support staff on key operational processes and industry knowledge, fostering a culture of continuous improvement and team development.
• Performs general oversight duties including maintaining group profiles, preparing reports, and executing all assigned tasks to support overall client retention efforts.
• Understands Healthcare Reform, HIPAA, COBRA, and other legislation affecting the business unit; guides clients in executing appropriate steps to meet regulatory requirements and validates that client decisions meet ACA compliance guidelines (affordability, minimum coverage, preventive care, etc.).
• Pursues further education and professional designations to deepen expertise; develops leadership capabilities in the planning, execution, and delivery of special projects as needed.
• All other duties as assigned.
What You’ll Need
• A college degree is an advantage but not a requirement
• Life, Health & Accident License required
• Professional designation of RHU, GBA, CEBS, PHR, or similar industry-related credential required
• At least 5 to 10 years of industry experience required, including medical benefits and ancillary lines of coverage
• Strong tactical skillset with demonstrated ability to execute
• General understanding of technical concepts — self-funding, alternative funding mechanisms, carrier solutions, etc.
• Strong relationship skills with clients, carriers, and internal partners
• Self-starter with the ability to work independently and know when to loop in the Client Executive or leadership for escalated issues
• Ability to oversee CSAs and provide general tactical oversight of support staff
• Project management skills: ability to work with internal and external partners to deliver results on time
Who You Are
• Energetic and eager to grow — continuously learning and developing new skills
• Highly organized with the ability to shift quickly between priorities without losing momentum
• A logical problem-solver who works well independently and thrives under pressure
• Positive and consistent — leads by example and brings a collaborative mindset to every interaction
• Strong verbal and written communicator who knows how and when to communicate, and with whom
• Interpersonally skilled with a naturally collaborative approach to internal and external partnerships
• Effective at managing time-sensitive projects and meeting established deadlines
• A natural mentor — able to guide others professionally and develop subordinates’ capabilities
Travel Expectations
• Moderate Travel (10–35%)
o Regular local and occasional overnight travel (up to 35%) may be required, including by car or air, depending on business needs.
o Travel may include visits to regional offices, client meetings, or industry events.
Physical and Environmental Demands
This role involves typical duties performed in an office environment. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
• Physical Requirements: Primarily sedentary work involving sitting, typing, and handling office equipment. Occasional walking, standing, and lifting up to 10 pounds may be required.
• Manual Dexterity & Vision: Requires sufficient manual dexterity and visual acuity for computer use, data analysis, and document preparation.
• Work Environment: Standard indoor office setting with moderate noise levels and climate control.
Work Schedule & Hours
Full-time hours: Core business hours of Monday through Friday from 8:00 AM to 5:00 PM and/or occasional weekend hours totaling 40 or more hours per week; no overtime payable. (FLSA Status: Exempt)
Note: job responsibilities and travel expectations at this level will often require the performance of job duties beyond the normal workweek schedule.
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