Stop Loss Strategy Specialist

Imagine360

5d • Remote

About The Position

Imagine360 is seeking a Stop Loss Strategy Specialist to join the team! The Stop Loss Strategy Specialist supports the Stop Loss Strategy Manager (SLSM) team by managing overflow casework and contributing to key components of active, high-impact cases. This role is designed to ensure continuity, organization, and efficiency across the stop loss workflow by advancing cases that require dedicated focus while also providing tactical support on more complex opportunities. Operating as a shared resource, this position is not aligned to specific sales representatives but instead flexes across the team to meet evolving business needs. This is a junior-level role with a strong emphasis on execution, coordination, and process support, playing a critical part in maintaining momentum across the pipeline within a fast-paced, performance-driven environment.

Requirements

• Bachelors degree or years of experience accepted in lieu of degree required.
• Strong organizational skills with the ability to manage multiple tasks and priorities simultaneously.
• High attention to detail and accuracy in handling documentation and data.
• Effective communication skills, both written and verbal.
• Ability to work in a fast-paced, deadline-driven environment.
• Team-oriented mindset with a willingness to support across functions.

Nice To Haves

• 1-3 years of experience in insurance, employee benefits, stop loss, or a related field preferred.

Responsibilities

• Manage and advance stop loss cases requiring dedicated coordination and follow-through, ensuring consistent progress across the pipeline.
• Support SLSMs on complex and time-sensitive cases by assisting with follow-ups, gathering and organizing documentation, and tracking outstanding items.
• Coordinate internal and external communications to ensure timely responses and seamless movement of cases through the pipeline.
• Maintain accurate and well-organized case files, ensuring all required documentation is complete, current, and easily accessible.
• Monitor case status and proactively identify items requiring attention, escalation, or resolution.
• Partner with underwriting, sales, and internal stakeholders to facilitate efficient and effective case progression.
• Assist in preparing case materials, proposals, and presentations to support client and broker engagement.
• Support reporting and tracking of pipeline activity to provide visibility into case progress, timelines, and workload.
• Identify and recommend opportunities to improve processes, organization, and overall team efficiency.
• Perform other duties as assigned.

Benefits

• Multiple Health plan options
• Company paid employee premiums for disability and life insurance
• Parental Leave Policy
• 20 days PTO to start
• 10 Paid Holidays
• Tuition reimbursement
• 401k Company contribution
• Company paid Short & Long term Disability plus Life Insurance
• Professional development initiatives / continuous learning opportunities
• Opportunities to participate in and support the company's diversity and inclusion initiatives

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level