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 solid 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 difference and lasting impact

Work in an agile, collaborative, progressive, and high-performing team

The opportunity to interface with executives from many different parts of the organization

Our Workplace:
We regard our employees as our most valuable asset and strive to create positive workplace culture and an environment that is fair, equitable, respectful and supportive. We encourage you to submit your application online for an opportunity to become part of our team.

Join Caldwell and be part of a highly engaged and collaborative team, where employees:

(i) can reach their full potential,

(ii) consistently deliver high-quality client experiences; and

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Caldwell does not use artificial intelligence (AI) to screen job applicants.

Caldwell is an equal opportunity employer.

C aldwell Securities Ltd. is committed to the principles of employment equity and diversity. We are dedicated to removing barriers in the recruitment and selection processes. We encourage members of equity seeking groups, including people with disabilities, to apply. Should you require accommodation, we will take into account your accessibility requirements. If we call you for an interview or any selection process, please notify us about your accommodation needs.

We thank all applicants. Only those selected for an interview will be contacted.

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📌 Compliance Supervisor (Ontario)
🏢 Caldwell Securities
📍 Ontario