Director, Compliance and Field Supervision

Hightower • Chicago, IL

5d • $150,000 - $160,000 • Hybrid

About The Position

Hightower is a wealth management firm and registered investment advisor providing investment, financial, and retirement planning services, as well as corporate consulting and cash management services. The Director of Compliance and Field Supervision provides leadership and oversight for Hightower’s nationwide branch-office network and helps lead the firm’s supervisory program. The role reports to the Head of Field Supervision and serves as Supervisory Principal for the Chicago Office (OSJ).

The director ensures advisor and branch activities comply with applicable laws, regulations, and internal policies and procedures. The position requires deep knowledge of registered investment adviser and broker-dealer regulation, sound independent judgment, and the ability to identify risk, strengthen supervisory controls, and foster a positive culture of compliance. The director works across business, operations, legal, risk, and technology teams and uses data, technology, and artificial intelligence tools to improve risk identification and supervisory effectiveness.

The position is based in the Chicago office, with in-office work Monday through Thursday and work from home on Fridays. Hightower offers a base salary of $150,000–$160,000 plus a discretionary bonus; the exact base salary depends on experience. Candidates must have unrestricted U.S. work authorization and must not require sponsorship now or in the future.

Requirements

• At least seven years of progressively responsible compliance or supervisory experience with a registered investment adviser, broker-dealer, or dually registered financial-services firm.
• Deep knowledge of SEC and FINRA requirements and their application within a complex wealth-management business.
• Significant experience with branch-office supervision, supervisory controls, and compliance risk management.
• Ability to analyze complex regulatory and business issues, assess practical implications, and develop effective solutions.
• Strong leadership and influencing skills, with the ability to work effectively across teams and levels of authority.
• Exceptional critical-thinking, written-communication, and verbal-communication skills.
• Collaborative and practical approach to compliance, including the ability to educate, advise, and appropriately challenge business partners.
• Sound judgment and decision-making skills, including the ability to recognize when matters require escalation.
• Strong organizational, project-management, and process-improvement skills, including the ability to prioritize competing responsibilities and deliver accurate, high-quality work on time.
• Proactive, responsive, and accountable working style, with the ability to operate independently and collaborate effectively.
• Proficiency with Microsoft Office applications and artificial intelligence tools such as ChatGPT, Claude, and Microsoft Copilot.
• Active Series 7, 24, 9/10, and 63 and 65 or 66 securities licenses.
• Active Life, Health, and Variable Annuity licenses.
• Unrestricted U.S. work authorization and no need for U.S. work-authorization sponsorship now or in the future.

Responsibilities

• Direct and perform supervisory functions across Hightower’s nationwide branch-office network.
• Help lead the firm’s supervisory program and ensure advisor and branch activities comply with applicable laws, regulations, and internal policies and procedures.
• Monitor regulatory developments and assess their impact on business practices, supervisory processes, and the firm’s control framework.
• Provide practical guidance to advisors, advisor staff, and business leaders on registered investment adviser and broker-dealer compliance requirements.
• Promote awareness of policies and procedures through clear, proactive communication and education.
• Partner with business, operations, legal, risk, and technology teams to achieve appropriate compliance outcomes while minimizing unnecessary disruption to advisors and clients.
• Identify, analyze, document, and escalate compliance issues, emerging risks, and recurring trends using sound judgment and independent decision-making.
• Recommend and implement improvements to supervisory controls, policies, procedures, monitoring activities, and related workflows.
• Use data, technology, and artificial intelligence tools to strengthen risk identification, decision-making, efficiency, and supervisory effectiveness.
• Lead or support departmental and enterprise-wide initiatives, set priorities, coordinate deliverables, and maintain accountability through completion.
• Foster a compliance culture grounded in accountability, collaboration, responsiveness, and sound risk management.
• Serve as the Supervisory Principal for the Chicago Office (OSJ).

Benefits

• Medical, dental, and vision insurance coverage beginning on the first day of employment.
• Paid parental leave: 16 weeks for a primary caregiver and 8 weeks for a secondary caregiver.
• Onsite mother’s lounge.
• Flexible PTO plan.
• Free, brand-new gym in the Chicago office.
• 401(k) matching plan.
• HSA employer contributions.
• Student loan assistance.
• Pet insurance.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed