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Our client is a growing, tax-informed insurance and estate planning advisory practice specializing in ultra-high-net-worth business owners and family offices. They are seeking a Senior Manager, Case Strategy & Planning Operations to own the end-to-end execution of complex insurance and estate planning files. This is a senior orchestration role, not a sales position — built for someone who thrives on structured execution, technical precision, and working alongside an elite advisory team.
What’s in It for You
- Base salary: $80,000 – $100,000+ based on experience
- Discretionary annual performance bonus
- Health, dental, and HSA coverage
- RRSP matching after 3 months
- Unlimited vacation
- Premium downtown Toronto office environment
Key Responsibilities
- Own the end-to-end flow of complex business-owner and HNW files from intake through policy placement
- Coordinate with clients, accountants, lawyers, and major carriers (Sun Life, Manulife, Canada Life) to move files forward
- Track and manage the medical side of underwriting — APS files, blood and urine tests, and carrier requirements
- Ensure all documentation and underwriting packages are complete and accurate before escalation
- Write smaller term policies from A to Z as needed to support workflow continuity
- Prepare and review illustrations, planning summaries, and client-ready materials
- Conduct full internal file audits post-placement and maintain compliance-driven documentation
- Manage all policy placement workflows in EPIC and maintain CRM hygiene in HubSpot
- Develop case studies, strategy decks, and marketing collateral to support advisor enablement
- Provide ongoing pipeline and underwriting status reporting to senior leadership
- Oversee junior support staff on data accuracy and documentation standards
Team Environment
- Small, highly collaborative team, senior leadership and support staff working closely together daily
- Active pipeline of approximately 25 files currently in underwriting and approximately 100 accounts transitioning into applications
Qualifications
- 5 to 10 years of life insurance experience in underwriting, case management, or advanced planning
- LLQP (life license) active or previously held or active license strongly preferred
- Deep technical knowledge of life insurance structures, corporate-owned policies, estate planning, and medical underwriting
- Polished communicator, comfortable interacting with CFOs, lawyers, accountants, and family office advisors at the billionaire level
- Proficient in EPIC (required) and HubSpot or similar CRM systems
- Strong organizational skills with the ability to manage multiple complex files simultaneously and with minimal supervision
- Prefers structured execution and problem-solving over business development
Ideal Background
- Advanced planning or wealth transition teams at major banks or carriers
- Senior case strategy or case management roles within insurance MGAs
- Independent advisory environments serving HNW and business-owner clients
- Former advisors who understand insurance mechanics and client positioning but prefer an execution-focused role
At Aplin — together with our brands CompuStaff and Impact Recruitment — we connect great people with great organizations across North America. We believe diverse teams build stronger companies, and we welcome applicants from all backgrounds, experiences, and perspectives. We use AI tools to assist in a fair and efficient matching process, helping our recruiters connect the right people with the right opportunities. To be considered, applicants must be legally entitled to work in Canada, including holding any required permits. Our recruitment services are always free for job seekers.