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Compliance Supervisor

Job in Toronto, Ontario, C6A, Canada
Listing for: Caldwell Securities Ltd.
Full Time position
Listed on 2026-02-28
Job specializations:
  • Finance & Banking
    Regulatory Compliance Specialist, Financial Services, Financial Compliance, Risk Manager/Analyst
Salary/Wage Range or Industry Benchmark: 60000 - 80000 CAD Yearly CAD 60000.00 80000.00 YEAR
Job Description & How to Apply Below

Caldwell Securities Ltd. ("Caldwell") is a majority employee-owned investment dealer that has been providing sophisticated and experienced investment and wealth management advice to individuals and corporations since 1981. Caldwell’s primary business includes investment management services, mutual fund sales, and retail and institutional sales. Caldwell is a member of the Canadian Investment Regulatory Organization ("CIRO") and runs its own self-clearing operations.

About the Job:

We are searching for a Compliance Supervisor to join our Compliance team. The individual will report into the Chief Compliance Officer and provide support to the business, including retail and institutional sales staff and the trade desk, with a view to mitigating civil, regulatory and reputational risk for Caldwell Securities. Additionally, you will assist with special initiatives and projects as needed to respond to internal requests and regulatory changes and focus areas.

What

does the job do? Compliance Supervisor responsibilities:
  • Perform day-to-day supervisory compliance monitoring and testing associated with Caldwell’s compliance program, including business conduct and trading conduct compliance surveillance
  • Monitor and assess compliance by Caldwell staff and clients
  • Take lead on CIRO and other regulatory examinations
  • Provide advisory support by responding to routine and complex regulatory inquiries and escalations.
  • Assist with the complaint review, resolution and escalation process, ensuring compliance with CIRO and other applicable industry rules.
  • Provide support for regulatory initiatives, participate in internal working groups, and ad hoc projects as required.
  • Fulfill reporting obligations to various regulators
  • Support various regulatory reporting processes and assists other compliance programs, as required
  • Adhere to applicable regulations as well as all aspects of Caldwell’s policies and procedures
  • Investigate cases and perform initial case analysis to support senior compliance staff
  • Provide support and guidance to other departments on compliance matters
  • Assist with the supervision of client and account activity including conducting trade surveillance on equities, fixed income and other activities
  • Support various regulatory reporting processes and assists other compliance programs, as required
  • Perform day-to-day compliance monitoring and testing associated with Caldwell’s compliance program and regulatory reporting
  • Monitor and assess compliance by Caldwell staff and clients
  • Perform other duties, as assigned, to assist in all areas of compliance
  • Support other compliance programs, as required
What is required to succeed? Essential Qualifications and Competencies
  • University Degree related to business or finance
  • 3 to 5+ years of progressive experience with full-service Investment dealers
  • Ability to become registered in the category of Supervisor, within three months
  • Completion of Intermediate knowledge of the securities/investment or financial services industry, compliance practices and legal and regulatory requirements
  • Ability to manage conflict, negotiate and influence decision-making when dealing with colleagues, business partners, senior management and other key stakeholders.
  • Strategic mindset, solutions driven, strong interpersonal skills and a strong client service focus.
  • Superior communication skills, verbal and written
  • Effective at time-management, multi-tasking and delivering on short-term priorities while maintaining a long-term focus
  • Ability to respond to and drive change management.
  • Proficient in Microsoft Office (Word, Excel, Powerpoint)
  • Experience with Dataphile and Position Watch is an asset
  • Excellent analytical and investigative skills with strong attention to detail
  • Excellent interpersonal skills with the ability to present information to different audiences
  • Disciplined work ethic and committed to producing excellence in work output
  • Ability to work with minimum supervision
  • A strong commitment to customer service
  • Exceptional verbal and communication skills with the ability to communicate to all audiences in a clear and compelling manner
  • Strong organization and time management skills
  • High ethical standards and integrity
  • Natural curiosity and drive to learn
  • The ability to travel to branch locations
  • Knowledge of various financial products including equities, options & other derivatives, an asset
Additional Assets:
  • Canadian Securities Course (CSC)
  • Conduct and Practice Handbook Course (CPH)
  • Canadian Securities Institute (CSI) Canadian Compliance Course
  • CSI courses
What We Offer:

We thrive on the challenge to be our best, thinking progressively to keep growing, and working together to deliver trusted advice to help our clients thrive and communities prosper. We care about each other, reaching our potential, making a difference to our communities, and achieving success that is mutual.

  • A comprehensive Total Rewards Program including bonuses and group benefits
  • Leaders who support your development through coaching and managing opportunities
  • Ability to make a…
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