Director of AML, Regulatory Compliance & Project Management in Winnipeg

Highclere Capital is a growing, Ontario-based mortgage finance company focused on providing innovative lending solutions to underserved borrowers across Canada. With a sharp eye on compliance, service excellence, and responsible growth, we partner with mortgage professionals to deliver tailored financing with speed and integrity. As a remote-first team, we’re building a culture rooted in accountability, collaboration, and a shared commitment to doing the right thing, for our brokers, our partners, and one another.

As a member of the leadership team, the Director, AML, Compliance & Project Management will lead Highclere’s regulatory compliance and AML/ATF programs while driving projects that strengthen governance, operational integrity, and business efficiency. This position is both strategic and hands-on, requiring the ability to interpret complex regulatory requirements, assess organizational risk, lead cross-functional initiatives, and embed a culture of compliance and continuous improvement throughout the business.

Core Responsibilities

• AML/ATF & Sanctions Oversight
  • Develop, implement, and maintain Highclere’s AML/ATF and Sanctions Program, including policies, procedures, and internal controls, in alignment with FINTRAC guidelines and the PCMLTFA.
  • Oversee and manage outsourced AML/ATF service provider relationships, ensuring appropriate oversight, reporting, and testing.
  • Conduct annual AML/ATF risk assessments, gap analyses, and program self-assessments.
  • Monitor changes in legislation, trends, and risks, and update programs accordingly.
  • Liaise with regulators, industry associations, law enforcement, and internal/external auditors on all AML/ATF matters.
• Regulatory Compliance
  • Develop and maintain the corporate compliance framework, ensuring all regulatory requirements are identified, interpreted, and implemented across the business.
  • Advise the Leadership Team and business units on compliance risks, policy interpretation, and remediation strategies.
  • Lead the preparation for regulatory reviews/audits and ensure timely resolution of findings.
  • Support ongoing training for employees on compliance and AML/ATF obligations.
• Project Management
  • Lead cross-functional projects related to compliance, AML/ATF, and corporate priorities, ensuring initiatives are delivered on time and within scope.
  • Project manage senior leadership meetings, including agenda development, materials preparation, action tracking, and follow-up.
  • Partner with business leaders to assess and manage the regulatory and operational impacts of new products, services, or process changes.
  • Implement and monitor project plans, reporting progress, risks, and outcomes to senior leadership and the Board where required.
  • Drive continuous improvement by embedding project management discipline, clear accountability, and technology-enabled solutions across compliance and corporate processes.
• Leadership & Reporting
  • Provide regular compliance and AML/ATF metrics, trends, and risk indicators to the Leadership Team and Board.
  • Act as a trusted advisor to senior leadership, fostering a culture of ethical behaviour and risk awareness.

Skills & Experience

• Must-Have Qualifications
  • 8 - 10 years in AML/ATF compliance in financial services, with direct experience in Canadian regulatory frameworks.
  • Proven experience managing compliance programs, regulatory interactions, and third-party service providers.
  • Recognized AML certification (e.g., CAMS) preferred.
  • Bachelor’s degree in business, law, or a related discipline.
  • Demonstrated leadership in implementing compliance or AML frameworks from the ground up.
  • Strong technical acumen, with the ability to leverage compliance technology platforms, data analytics tools, and digital workflows.
  • Excellent communication, presentation, and relationship management skills.
• Nice-to-Have
  • Experience in mortgage lending, underwriting, or related credit risk functions.
  • Exposure to sanctions screening systems and automated compliance tools.
  • Experience leading multi-departmental projects or technology implementations.