Chief Operating Officer/Chief Compliance Officer

Hilltop Wealth Advisors, LLC • Chapel Hill, NC

2d • $200,000 - $250,000 • Hybrid

About The Position

Hilltop Wealth Advisors is growing, and we’re seeking a senior leader to serve as our Chief Operating Officer / Chief Compliance Officer. This role is designed to own Hilltop’s operational backbone end-to-end—building the management systems, process discipline, reporting infrastructure, and compliance execution required to support a high-growth, increasingly sophisticated wealth management firm. This position is ideal for a high-EQ, execution-oriented operator who can lead across functions, build structure inside a growing organization, and help transform Hilltop from a strong founder-led business into a more scalable firm. The right candidate may come from wealth management, financial services, insurance, accounting, legal, or another regulated professional-services environment, but must bring a proven ability to create clarity, accountability, and operating rigor. As Hilltop scales toward its long-term growth vision, this leader will play a central role in ensuring the business can execute consistently, manage complexity well, and operate with increasing confidence and discipline. The Chief Operating Officer / Chief Compliance Officer will be responsible for leading Hilltop’s internal operating system and strengthening the firm’s compliance execution. This leader will work closely with the executive team to improve management cadence, operational accountability, workflow consistency, KPI visibility, and cross-functional execution. This is not an administrative support role. It is a senior leadership seat responsible for helping the firm scale operationally. The person in this role must be able to translate strategy into execution, reduce friction and bottlenecks, improve reliability across the business, and create a stronger operating environment for future growth. The COO/CCO will also serve as the key internal owner of compliance execution, partnering closely with outside compliance support and internal stakeholders to ensure responsibilities are managed proactively, accurately, and on time.

Requirements

• Senior leadership experience in operations, business management, or a comparable executive operating role
• Demonstrated success building or improving systems, processes, and operating cadence in a growing business
• Experience improving accountability, workflow consistency, and cross-functional execution
• Strong ability to build dashboards, reporting structures, and KPI visibility
• Experience operating in a regulated, high-accountability, or professional-services environment
• Strong communication skills, executive presence, and ability to influence across teams
• High ownership, sound judgment, and strong follow-through

Nice To Haves

• Experience in wealth management, RIA, financial services, insurance, accounting, legal, or related sectors
• Experience partnering with outside compliance, legal, or risk specialists
• Familiarity with CRM/workflow systems and operational reporting infrastructure
• Experience in founder-led, entrepreneurial, or scaling businesses where systems had to be built, not just managed

Responsibilities

• Build and strengthen Hilltop’s operating system, including leadership meeting cadence, accountability rhythms, and follow-through mechanisms
• Improve cross-functional execution so strategic priorities move from discussion into consistent implementation
• Identify bottlenecks, breakdowns, and inefficiencies across the business and lead efforts to solve them
• Increase organizational clarity by defining process ownership, handoffs, and accountability standards
• Help leadership create a more scalable business model with less founder dependency
• Improve process consistency across core workflows, including client service, advisor support, internal operations, and cross-functional coordination
• Strengthen CRM discipline, workflow reliability, and systems adoption across the organization
• Partner with team leaders to ensure key processes are documented, maintained, and scalable
• Help architect the internal infrastructure needed for future growth, complexity, and multi-leader execution
• Build and improve operational dashboards and reporting systems that provide leadership with better visibility into performance
• Ensure key metrics are tracked consistently and used to inform decision-making
• Improve the quality, reliability, and usefulness of internal reporting across departments
• Support a culture of data-informed management rather than reactive decision-making
• Own the internal execution of Hilltop’s compliance responsibilities in partnership with outside compliance experts and legal/regulatory resources
• Ensure compliance tasks, calendars, documentation, reviews, and follow-up items are completed on time and to a high standard
• Improve compliance-related workflows so they are less reactive, less fragmented, and more consistently managed
• Serve as the internal leader ensuring compliance discipline is integrated into how the firm operates
• Serve as a trusted thought partner to the executive team on operational scaling, execution challenges, and organizational readiness
• Help create greater accountability and follow-through across the leadership team
• Support the evolution of the firm’s structure, systems, and operating model as Hilltop grows
• Bring calm, clarity, and rigor to a fast-moving, growth-oriented environment

Benefits

• medical
• dental
• vision
• life insurance
• 401(k) with employer match
• generous paid time off
• volunteer time off
• flexible work-from-home policy (up to five days per month, with Monday and Thursday designated for in-office collaboration)
• ongoing educational reimbursement opportunities

What This Job Offers

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