Director, Compliance and Field Supervision

Hightower•Chicago, IL

11d•$150,000 - $160,000•Hybrid

About The Position

Hightower is a wealth management firm providing 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 Director of Compliance and Field Supervision is part of the Compliance Department, which supports advisor practices and develops processes and strategies that meet regulatory requirements while serving advisors, clients, and internal teams. Reporting to the Head of Field Supervision, this leader oversees the firm’s nationwide branch-office network and helps lead its supervisory program. The role requires extensive knowledge of registered investment adviser and broker-dealer regulations, independent risk judgment, strong communication, and the ability to strengthen supervisory controls and promote a positive culture of compliance. The position also serves as Supervisory Principal for the Chicago Office (OSJ). The role is based in the Chicago office, with an in-office schedule Monday through Thursday and work from home on Fridays. Hightower offers a base salary of $150,000–$160,000 plus a discretionary bonus; the specific 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 how they apply within a complex wealth-management business.
Significant experience with branch-office supervision, supervisory controls, and compliance risk management.
Demonstrated ability to analyze complex regulatory and business issues, assess practical implications, and develop effective solutions.
Strong leadership and influencing skills, including 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 recognizing 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, without a need for 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, setting priorities, coordinating deliverables, and maintaining 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.
In-office Monday through Thursday and work from home on Fridays.
Free 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; exact base salary depends on experience.