Accounting Operations & Executive Support Associate

Sterling Insurance Brokers Ltd.
Remote / Hybrid

About Sterling

Sterling Insurance Brokers Ltd. is a growing Canadian commercial insurance brokerage serving businesses across multiple industries. We pride ourselves on delivering responsive, professional service while maintaining strong operational discipline behind the scenes.

As we continue to grow, we are seeking two highly capable, organized, detail-oriented, and professional Accounting Operations & Executive Support Associates to support our finance, operations, and leadership teams.

This is a multifaceted role combining bookkeeping support, operational coordination, administrative support, brokerage assistance, and client-facing responsibilities.

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The Opportunity

This is not a traditional bookkeeping-only role.

The successful candidate will support the day-to-day financial and operational workflows of the brokerage while also assisting senior management with administrative coordination, scheduling, communication management, and ad hoc business support tasks.

You will work closely with the Accounting Manager / Controller while also supporting senior leadership as operational priorities arise.

This role is ideal for someone who is highly organized, adaptable, polished, proactive, and comfortable wearing multiple hats in a fast-paced business environment.

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Key Responsibilities

Accounting & Financial Operations

• Record daily financial transactions accurately and consistently
• Maintain organized and up-to-date accounting records
• Track accounts receivable and assist with collections follow-up
• Process accounts payable and prepare payment schedules
• Assist with client refund processing and payment documentation
• Support bank and account reconciliations
• Match financial records against internal systems and identify discrepancies
• Assist with month-end close support and reporting preparation

Administrative & Executive Support

• Monitor and assist in managing calendars, schedules, and appointments
• Support email monitoring, follow-up coordination, and administrative correspondence
• Assist with internal task coordination and workflow management
• Help ensure priorities are tracked and operational items are followed through
• Provide general executive and administrative support to senior management as required

Operations / Brokerage Support

• Support senior leadership with ad hoc brokerage operations tasks
• Assist with underwriting support tasks as required
• Help prepare documents, submissions, reports, presentations, and internal materials
• Support operational process execution across the business
• Maintain accurate documentation and records across systems
• Assist with special projects and strategic initiatives as required

Client Communication

• Take calls with clients and provide professional assistance where required
• Communicate clearly and professionally via phone and email
• Present information confidently and accurately
• Represent Sterling in a polished and professional manner

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Qualifications

Required

• Minimum Bachelor’s degree from an accredited university (any discipline accepted)
• 1–3+ years of professional experience in bookkeeping, accounting support, operations, executive assistance, administrative coordination, or similar business support roles
• Experience working with CRM and/or ERP software platforms
• Candidates must clearly reference specific systems used in their resume and/or cover letter
• Strong working knowledge of:
• Accounts Receivable
• Accounts Payable
• Basic reconciliations
• Transaction processing
• Strong Excel / spreadsheet proficiency
• Excellent written and verbal communication skills
• Strong presentation and interpersonal skills
• Professional phone presence and client communication ability
• Exceptional organizational skills and attention to detail
• Ability to manage multiple moving priorities effectively

Preferred / Asset

• Experience in an insurance brokerage, MGA, underwriting, financial services, or related industry
• Familiarity with Applied Epic or similar insurance management systems
• Experience supporting senior leadership or executives
• Experience in high-volume operational environments

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What Success Looks Like

• Accurate bookkeeping and financial support
• Organized and responsive administrative execution
• Professional and polished client interactions
• Reliable support for leadership and operations
• Strong follow-through and task ownership
• Ability to adapt quickly as business needs evolve

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Reporting Structure

This role will work under the supervision of the Accounting Manager / Controller, while also supporting senior leadership across the business as required.

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How to Apply

Please submit your application through OnlineJobs PH only.

Email applications will not be reviewed.

Your application must include:

• One combined PDF containing both your resume and cover letter
• Cover letter should be addressed to Ibrahim Asadullah, Chief Strategy Officer

Your cover letter should specifically explain:

• Your relevant professional experience
• Your experience working with CRM and/or ERP software platforms (please reference specific systems used)
• Any experience in client-facing roles, executive support, insurance, underwriting, brokerage operations, or financial services
• Why you believe you are a unique fit for this role

If you have worked in insurance, underwriting, brokerage operations, or financial services, please highlight this clearly.

To confirm you have carefully read this posting, please begin your application message with the following exact heading:

Sterling (Last Name, First Name)