AML Officer - NA & Carribean

Location: Chicago, New York DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk. Headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia, we trade a variety of asset classes including Fixed Income, ETFs, Equities, FX, Commodities and Energy across all major global markets. We have also leveraged our expertise and technology to expand into three non-traditional strategies: real estate, venture capital and cryptoassets. We operate with respect, curiosity and open minds. The people who thrive here share our belief that it’s not just what we do that matters–it's how we do it. DRW is a place of high expectations, integrity, innovation and a willingness to challenge consensus. The AML Officer - North America & Caribbean is a senior role responsible for designing, owning, and continuously strengthening Cumberland's AML/CTF and sanctions compliance programs across its U.S., Canadian, and Caribbean-domiciled entities. This position serves as the primary AML authority and point of accountability for regulatory engagement, program governance, risk assessment, and BSA/AML policy across the region. The role oversees the full lifecycle of the AML program, from policy and procedure development through program execution, regulatory reporting, and examination management, across a portfolio of entities operating under U.S. federal and state (NYDFS), Canadian (FINTRAC), British Virgin Islands (BVIFSC), and Cayman Islands (CIMA) regulatory frameworks. Th  AML Officer works closely with the Global Head of Financial Crimes, senior leadership, legal counsel, outside advisors, and regulators to ensure the firm meets its obligations and leads with a culture of compliance. Key Responsibilities Program Ownership & Governance AML Program Leadership: Serve as the senior AML authority for all North American and Caribbean entities; own the design and execution of the AML/CTF and sanctions compliance program for these entities. Policy & Procedure Authority: Develop and maintain AML/CTF and sanctions policies and procedures across all regional entities; ensure policies reflect current regulatory requirements, enforcement trends, and the firm's evolving business activities. Risk Assessment: Lead the development and annual refresh of enterprise-wide AML risk assessments; identify inherent and residual risk across customer, product, geographic, and channel dimensions; present findings and risk ratings to senior management and boards. Lead control enhancement and remediation strategy for self-identified issues. Program Governance: Establish and maintain program governance frameworks including issue management, findings tracking, escalation protocols, and management reporting; ensure open items are remediated on schedule and program gaps are surfaced proactively. Senior Management & Board Reporting: Prepare and deliver periodic AML program reports to senior management, boards, and governance committees across entities; provide clear, data-driven assessments of program health, risk posture, and remediation status. Regulatory Compliance & Examination Management Regulatory Relationship Management: Serve as the primary AML point of contact for regulators across the region, including FinCEN, NYDFS, FINTRAC, BVIFSC, and CIMA. Examination Preparation & Response: Lead preparation for regulatory examinations and internal/external audits; coordinate document production, draft cover narratives, manage examiner meetings, and oversee remediation of examination findings. Regulatory Reporting Oversight: Oversee the timely and accurate filing of required regulatory reports across jurisdictions, including SARs (FinCEN), STRs (FINTRAC), and equivalent suspicious transaction reporting obligations in BVI and Cayman; review and approve material filings. Regulatory Change Management: Monitor and assess emerging AML regulatory developments across all applicable jurisdictions; evaluate impact on the firm's program and business activities; translate regulatory changes into actionable policy and procedure updates. Jurisdictional AML Program Management United States - Federal: Maintain deep expertise in U.S. federal AML obligations under the Bank Secrecy Act (BSA), USA PATRIOT Act, FinCEN regulations, and OFAC sanctions requirements; oversee program components including CIP, CDD, EDD, transaction monitoring, SAR filing, and recordkeeping for U.S.-domiciled entities. United States - New York (NYDFS): Manage compliance with NYDFS-specific requirements applicable to Cumberland's New York licensed entity, including NYDFS Part 504 (Transaction Monitoring and Filtering Program requirements), BitLicense obligations under 23 NYCRR 200, and annual certification obligations; serve as the NYDFS AML contact and manage examination and inquiry responses. Canada (FINTRAC): Oversee AML/CTF compliance for DRW's Canadian operations under the Proceeds of Crime (Money Laundering) and Terrorist Financing Act (PCMLTFA) and FINTRAC regulations; ensure obligations are met with respect to client identification, beneficial ownership, transaction reporting, and STR filing; maintain FINTRAC registration and manage examination readiness. British Virgin Islands (BVIFSC): Oversee AML/CTF and sanctions compliance for BVI-domiciled entities under the Proceeds of Criminal Conduct Act, the Anti-Money Laundering and Terrorist Financing Code of Practice, and applicable BVIFSC guidance; manage BVIFSC relationship, examination responses, and STR obligations to the BVI Financial Intelligence Agency (FIA); ensure policies reflect 2025 BVIFSC inspection findings and updated AML/CTF/sanctions requirements. Cayman Islands (CIMA): Maintain program compliance for Cayman-domiciled entities under the Proceeds of Crime Law (PCL), Anti-Money Laundering Regulations (AMLRs), and Guidance Notes on the Prevention and Detection of Money Laundering and Terrorist Financing; ensure obligations are met with respect to customer due diligence, suspicious activity reporting to the Cayman Islands Financial Reporting Authority (CIFRA), and CIMA oversight requirements. Investigations & Financial Intelligence Escalation Authority: Serve as the final escalation point for complex or sensitive AML investigations, alert dispositions, and SAR/STR filing decisions across all regional entities; provide guidance on novel or high-risk fact patterns. SAR/STR Filing Decisions: Review and approve SAR and STR filings across jurisdictions; ensure filings are complete, accurate, timely, and appropriately documented; maintain a filing log and oversee recordkeeping obligations. Sanctions Program Oversight: Oversee OFAC and equivalent sanctions screening programs across entities; review and approve responses to potential matches; ensure screening coverage is appropriate for the firm's counterparty and transaction profiles. Blockchain Analytics Oversight: Direct the use of blockchain analytics tools (Chainalysis, TRM Labs, or equivalent) within the AML program; ensure alert thresholds, risk scoring, and investigation protocols are calibrated appropriately and reviewed periodically. Crypto Financial Crime Typologies: Maintain current, deep knowledge of financial crime typologies specific to digital asset markets; apply typology knowledge to refine the effectiveness of the program. Program Influence & Stakeholder Engagement Training Program: Develop and deliver AML training programs for compliance staff, operations, the business, and senior management; ensure training is current, jurisdiction-specific where required, and appropriately documented; track completion and maintain training records. Cross-functional Engagement: Partner with legal, operations, technology, and trading to ensure AML program requirements are understood and embedded into business workflows; provide timely, well-reasoned guidance on counterparty activity, policy questions, and escalated matter. Program Influence Without Direct Authority: Drive program outcomes and accountability across the AML function through influence, expertise, and collaborative engagement; build strong working relationships with AML analysts, operations teams, and business stakeholders to ensure program standards are consistently applied. Required Qualifications Experience: 10+ years of BSA/AML compliance experience, including at least 3-5 years in a senior AML officer, deputy officer, or equivalent leadership role at a financial institution, digital asset firm, or regulated entity. Multi-jurisdictional AML Expertise: Demonstrated, hands-on knowledge of AML/CTF regulatory frameworks across at least two of the following: U.S. federal (BSA/FinCEN/OFAC), NYDFS, Canada (FINTRAC/PCMLTFA), British Virgin Islands (BVIFSC), or Cayman Islands (CIMA); willingness and ability to rapidly develop proficiency across all five jurisdictions. Program Design & Ownership: Proven track record of designing, implementing, or materially improving an AML/CTF compliance program at regulated financial institutions; experience owning policies, risk assessments, and governance frameworks. Regulatory Engagement: Direct experience preparing for and responding to regulatory examinations, inquiries, or audits; ability to manage examiner relationships professionally and produce high-quality regulatory responses under deadline pressure. Investigations & SAR Authority: Experience serving as a SAR/STR review and approval authority; strong judgment on escalation decisions, complex alert dispositions, and novel financial crime typologies relevant to digital asset trading. Digital Assets Experience: Prior experience in a virtual currency, crypto trading, or digital asset compliance environment; familiarity with blockchain analytics tools such as Chainalysis and Elliptic and the financial crime risks unique to crypto markets. Communication & Executive Presence: Exceptional written and verbal communication skills; demonstrated ability to present complex compliance matters clearly to boards, senior executives, and regulators; experience drafting board-level compliance reports and regulatory submissions. Ability to lead and collaborate efficiently with AML and external resources. Judgment & Independence: Sound independent judgment on ambiguous regulatory questions; comfortable operating in fast-moving, high-accountability environments with limited precedent. Preferred Qualifications Regulatory Experience: Prior experience as a regulator, examiner, or compliance officer embedded in a regulatory examination process at FinCEN, NYDFS, FINTRAC, BVIFSC, CIMA, or a comparable authority. NYDFS Expertise: In-depth knowledge of NYDFS Part 504 certification requirements, BitLicense obligations, and NYDFS examination procedures; prior experience managing a NYDFS examination or enforcement matter. Caribbean Jurisdiction Experience: Hands-on experience operating an AML/CTF program under BVI (BVIFSC) or Cayman (CIMA) regulatory frameworks, including familiarity with local legislative requirements, reporting obligations, and examination practices. Canada FINTRAC Experience: Direct experience managing a FINTRAC-registered AML compliance program, including registration maintenance and FINTRAC examination readiness. Multi-entity Program Management: Experience managing AML programs simultaneously across multiple legal entities, jurisdictions, or business lines with distinct regulatory obligations and risk profiles. Sanctions Expertise: Advanced knowledge of OFAC sanctions compliance, including SDN screening, secondary sanctions considerations, and voluntary self- disclosure processes; experience with equivalent sanctions regimes (UN, EU, UK, Canada) a plus. The annual base salary range for this position is $160,000 to $215,000 depending on the candidate’s experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus. In addition, DRW offers a comprehensive suite of employee benefits including group medical, pharmacy, dental and vision insurance, 401k (with discretionary employer match), short and long-term disability, life and AD&D insurance, health savings accounts, and flexible spending accounts. For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at https://drw.com/privacy-notice . California residents, please review the California Privacy Notice for information about certain legal rights at https://drw.com/california-privacy-notice . #LI-DW1