Health Insurance jobs in Toronto, ON

About Stalwart Insurance Brokers Ltd.

Stalwart Insurance Brokers Ltd. (Stalwart) is a growing national life insurance brokerage with a focus on high-complexity client and business situations. We value excellence and entrepreneurial thinking, requiring staff with the capacity to solve complex, novel problems. As we continue our rapid growth, we are looking for ambitious team members who are eager to scale their skills, abilities, and relationships.

Summary

We are looking for an Insurance Lead with an accounting background to join our Vancouver or Toronto office. This is a technical account-management role combining financial analysis, insurance administration, client-file management, and operational improvement.

The Insurance Lead will work with detailed financial records, legal entity structures, cash flows, reconciliations, insurance policies, financing arrangements, and complex client documentation. The role will involve coordinating with clients, lenders, insurance companies, legal counsel, accountants, and other professional advisors to ensure client files and insurance structures are accurately maintained and managed.

Insurance experience is an asset, but it is not required. We are particularly interested in candidates with a strong accounting or financial background who are comfortable working with complex information, have strong attention to detail, and are interested in developing expertise in life insurance and complex insurance structures.

Responsibilities

Your responsibilities will include, but will not be limited to:

• Prepare and maintain annual flow-of-funds models showing transactions among clients, lenders, insurance companies, corporations, trusts, and other entities
• Review premium schedules, financing arrangements, policy values, ownership records, and related financial information for completeness and consistency
• Reconcile policy and financing information to supporting documents, lender statements, insurer records, and internal schedules
• Maintain accurate continuity schedules for premiums, loans, interest, policy values, and other key financial data
• Analyze variances from prior-year models and investigate unusual or inconsistent amounts
• Prepare clear financial summaries, reports, and presentations for clients, executives, lenders, and professional advisors
• Support accounting and tax information requests by organizing accurate source data and coordinating with external accountants and other advisors
• Assist with tracking fees, invoices, cash requirements, deadlines, and other financial commitments associated with client insurance structures
• Coordinate annual policy renewals and premium-financing activities with clients, lenders, insurers, and internal team members
• Notify clients and lenders of upcoming renewal requirements, expected cash flows, documentation needs, and key dates
• Coordinate client meetings to review annual policy and financing information
• Support the preparation and review of client, policy, lender, and ownership documentation
• Assist with insurance applications, renewals, policy changes, ownership updates, and other servicing requirements
• Maintain complete and accurate client and policy records across systems
• Follow up with insurers, underwriters, lenders, legal counsel, accountants, and other service providers on outstanding items
• Respond to client questions and coordinate input from the appropriate technical or professional advisors
• Build and maintain checklists, reconciliations, review controls, and standardized workpapers for recurring insurance processes
• Identify gaps, inconsistencies, missing documents, and control risks before they affect a renewal, financing, or client deliverable
• Track key performance measures, outstanding items, turnaround times, and upcoming deadlines
• Identify and implement process improvements, automation opportunities, templates, and best practices
• Support executives and managers in planning and executing operational and strategic initiatives
• Manage multiple client files and deadlines while maintaining clear documentation and accountability

Required Skills and Experience

• Undergraduate degree in accounting, commerce, business, finance, or a related field
• CPA designation, CPA candidacy, or meaningful progress toward an accounting designation is preferred, but not required
• 2–5 years of experience in accounting, public practice, financial reporting, corporate finance, family office, banking, or another detail-oriented financial role
• Strong Excel skills, including the ability to build and review multi-entity schedules, cash-flow models, reconciliations, and analytical workpapers
• Ability to understand transactions and relationships involving corporations, trusts, lenders, insurers, and individual clients
• Experience reviewing source documents and maintaining accurate supporting documentation for calculations and decisions
• Comfort working with legal agreements, financial statements, tax information, lender documents, insurance documentation, and other technical records
• Excellent verbal and written communication skills when working with clients, executives, lenders, insurers, professional advisors, and internal team members
• Exceptional attention to detail and a strong commitment to accuracy and consistency
• Strong organizational and time-management skills, with the ability to manage recurring annual cycles, multiple files, and competing deadlines
• Sound judgment and the ability to identify when information is incomplete, inconsistent, or requires escalation
• A proactive and resourceful approach to work, with the ability to take ownership of a file and move assignments forward with limited direction
• Ability and willingness to learn quickly and develop knowledge of specialized insurance concepts
• Strong problem-solving skills and an interest in process design, controls, automation, and continuous improvement
• Professional and client-focused approach when working with business owners, executives, lenders, insurers, and professional advisors

Insurance Experience

Experience in life insurance, underwriting, insurance operations, premium financing, or policy administration is considered an asset, but is not required.

The successful candidate will receive training and develop working knowledge of life insurance products, policy administration, premium financing, and complex insurance structures. We are particularly interested in candidates who bring a strong accounting mindset and want to build specialized expertise in complex life insurance and high-value client situations.

Salary and Benefits

• Salary: 150K - 160K per year, commensurate with experience, plus bonus
• Benefits: Extended health benefits plan

Position Type

• Nature: Permanent, full-time, in-person
• Time Commitment: 40 hours per week, with occasional overtime required
• Work Location: Toronto, ON or Vancouver, BC
• Start Date: Immediate

Please note: Candidates must be currently authorized to work in Canada.

We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, colour, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law.

Pay: $150,000.00-$160,000.00 per year

Work Location: In person