Director, Compliance and Field Supervision

Hightower Advisors•Chicago, IL

10d•$150,000 - $160,000•Hybrid

About The Position

Hightower is a wealth management firm founded in 2008 that provides investment, financial, and retirement planning services to individuals, foundations, and family offices, as well as 401(k) consulting and cash management services to corporations. The firm is based in Chicago and operates as a registered investment advisor, with advisors across the United States. The Director of Compliance and Field Supervision reports to the Head of Field Supervision and helps oversee Hightower’s nationwide branch-office network. This leader performs and directs supervisory functions, helps lead the firm’s supervisory program, and works to ensure advisor and branch activities comply with applicable regulations and internal policies. The role identifies and manages compliance risks, advises business partners, improves supervisory controls and workflows, and promotes a culture of accountability and sound risk management. The position partners with business, operations, legal, risk, and technology teams; monitors regulatory developments; and uses data, technology, and artificial intelligence tools to improve risk identification and supervisory effectiveness. The role also leads or supports departmental and enterprise-wide initiatives. The Director will serve as the Supervisory Principal for the Chicago Office (OSJ). The role is in-office Monday through Thursday and remote on Fridays. Hightower offers medical, dental, and vision coverage beginning on the first day of employment, paid parental leave, a flexible PTO plan, an onsite gym, 401(k) matching, HSA employer contributions, student loan assistance, and pet insurance. Base salary is $150,000–$160,000, plus a discretionary bonus; the exact base salary depends on experience.

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; 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.
U.S. citizenship, U.S. permanent residency, or other unrestricted U.S. work authorization; no current or future sponsorship requirement.

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, establishing priorities, coordinating deliverables, and maintaining accountability from initiation 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 insurance coverage beginning on the first day of employment
Dental insurance coverage beginning on the first day of employment
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
Mother’s lounge onsite
Flexible PTO plan
In-office Monday through Thursday and work from home on Fridays
Free, brand-new gym in the Chicago office
401(k) matching plan
HSA employer contributions
Student loan assistance
Pet insurance
Base salary of $150,000–$160,000 plus discretionary bonus