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Regulatory Compliance Specialist

The Successful Investor
Posted Jul 2, 2026, 7:18 AM UTC
🇨🇦Canada🏢Hybrid📁Legal & Compliance
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REGULATORY COMPLIANCE SPECIALIST, Successful Investor Wealth Management Inc. We are an established wealth management firm with 20+ years’ experience in independent portfolio management with assets under management of $1 billion and growing. We are transforming our business and experiencing significant growth, and as a result, we are looking for development-oriented individuals to join our organization. As a registered firm under the Ontario Securities Commission (OSC), we prioritize integrity, fiduciary responsibility, and regulatory excellence. We are currently seeking a Regulatory Compliance Specialist to work alongside our CCO to help ensure our continued adherence to securities laws and regulatory best practices in a dynamic, client-focused environment. We are looking for a candidate committed to the area of compliance, seeking to advance their experience within the wealth management landscape and grow their responsibilities long term. The Regulatory Compliance Specialist plays a critical role in maintaining our firm’s compliance with applicable regulations and governing bodies, including those under the Ontario Securities Act, FINTRAC, CRA and OSC guidelines. This role will support our Chief Compliance Officer in managing day-to-day compliance operations, implementing compliance programs, and preparing for regulatory reviews and audits. In addition to primarily supporting compliance efforts, this role will also gain broad exposure to overall wealth management operations while participating in trade support and other administrative functions. KEY RESPONSIBILITIES Regulatory Compliance & Monitoring Monitor, interpret, and implement changes in OSC regulations, securities legislation, and other applicable rules, including FINTRAC and AML. Assist with ongoing review and enhancement of SIWM’s compliance framework, policies, and internal controls. Conduct periodic and ad-hoc internal compliance audits and risk assessments across relevant business activities; provide annual updates to the board as required. Support the maintenance of an effective compliance calendar to ensure all reporting and requirements are completed as required, within prescribed timelines. Support with investigating and responding to any client complaints or concerns pertaining to portfolio management activities. Registration & Reporting Assist with the preparation and coordination of regulatory filings, reporting, surveys, and audits. Manage ongoing compliance with Know-Your-Client (KYC), suitability, and client documentation obligations. Internal Advisory & Training Serve as a subject matter expert for staff on regulatory issues, suitability, conflicts of interest, and other compliance matters. Provide compliance training and guidance to management, portfolio managers, and operational staff. Review all external communications, i.e., marketing material and investor communications, for regulatory compliance. Audit & Examination Support Coordinate with internal and external auditors for compliance reviews. Prepare documentation and responses for OSC, FINTRAC, and CRA Pooled Fund Audits, compliance reviews, and regulatory inquiries. Act as the secondary contact person for OSC, FINTRAC, and CRA Pooled Funds audits. Trading – Execution, Management, and Reconciliation Execution of stock trades on behalf of the firm and its clients. Monitor trade activity to ensure compliance with regulatory and internal guidelines. Track order status for trade confirmations and settlements; Resolve issues such as failed trades or mismatches. Log FX conversions and reconcile trades at the end of the day to ensure accuracy. Generate and distribute trading reports to internal stakeholders and clients. Investigate and resolve trade breaks or discrepancies. Additional ad-hoc trade-related requests as required. Other Help optimize operational workflows and reduce manual errors within the scope of the role. Provide administrative support in other areas of Wealth Management as qualified and able, including Portfolio Management, Fund Accounting, and Client Services. REQUIREMENTS (Qualifications, Experience & Skills) Required: Bachelor’s degree in law, Finance/Accounting, Business, or related field. A CFA or CPA designation is preferred. Candidates actively pursuing either designation will also be considered, provided CFA candidates have completed Level I or higher. Minimum 3-5 years of experience working in regulatory compliance for a CSA-registered company. Strong understanding of compliance frameworks and risk management principles, including regulations as prescribed under governing bodies and standards, i.e., OSC, FINTRAC, AML, etc. Highly proficient in using Microsoft Excel. Excellent command of the English language, both written and verbal. Preferred: Completion of the Canadian Securities course (CSC). Completion of the CSI “Anti Money Laundering” course . Completion of the Partners, Directors, and Senior Officers course (PDO). Knowledge of laws affecting High Net Worth Investors, including Tax, Estates, and Trusts. Other Requirements: Excellent analytical, communication, and reporting skills. High level of integrity and attention to detail; handle a high degree of sensitive and confidential information appropriately. Ability to work independently and collaboratively in a fast-paced environment. Flexible to work after hours as needed. Excellent time management and organizational skills. Results-focused with a drive for continuous learning. High level of accountability for work and responsibilities. Proactive and initiative. This role is hybrid—one day remote and four days required in our office located near Yonge St. and Sheppard Ave. in North York, Toronto. We are seeking a dynamic and adaptable team member who can thrive in a fast-paced work environment to achieve our goals. Pre-employment work references, credit and criminal background checks are required. Additional Information Benefits After the standard three-month waiting period, successful new hires are eligible to join the Company’s Group Benefits Plan, which provides a range of life, health, and dental benefits, with premiums fully paid by the Company. After this same waiting period, transit commuters will also be eligible to participate in a generous reimbursement program to help subsidize public transportation costs to-and-from the office. To help foster our culture of appreciation, employees have an opportunity to participate in our company wide program to give and receive rewards and recognition for high performance and service. Other This posting is for an existing job vacancy. Successful Investor Wealth Management does not use artificial intelligence (AI) or automated decision-making systems to screen, assess, or select applicants for employment. All hiring decisions are made through human review of application materials, interviews, and assessments conducted by our recruitment team. Successful Investor Wealth Management Inc. welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

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