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Chief Operating Officer / Chief Compliance Officer 
Hilltop Wealth Advisors | Chapel Hill, NC 

Job Description Overview 
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. 

Role Summary 

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. 

Key Responsibilities 

Operational Leadership & Execution 

• 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 

Process, Systems & Infrastructure 

• 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 

Dashboards, Reporting & Management Visibility 

• 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 

Compliance Ownership 

• 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 

Leadership Partnership 

• 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 

What Success Looks Like 

Success in this role means Hilltop becomes more scalable, more disciplined, and more operationally reliable. 

In the first 12 months, the right person will help Hilltop: 

• Build a stronger operating rhythm across the leadership team 

• Improve follow-through and accountability on key strategic priorities 

• Increase process consistency and workflow reliability across the business 

• Strengthen CRM discipline and reduce dropped balls or execution gaps 

• Create better dashboards and reporting visibility for leadership 

• Reduce day-to-day executive bottlenecks 

• Improve compliance execution and coordination with outside support 

• Create a more durable operating foundation for long-term growth 

What Great Looks Like in 12 Months 

By the 12-month mark, the right person in this role will have helped Hilltop operate with materially more clarity, discipline, and scale. 

They will have: 

• Built a stronger operating rhythm across the business, including leadership meeting cadence, follow-up discipline, and cross-functional accountability 

• Improved process consistency across key workflows, reducing bottlenecks and improving execution reliability 

• Increased visibility into performance through better dashboards, reporting, and operational metrics 

• Strengthened CRM and workflow discipline so key processes are more repeatable and less dependent on individual memory or heroics 

• Created greater confidence that strategic priorities are actually being executed across departments 

• Reduced day-to-day executive bottlenecks by taking operational ownership of key initiatives and systems 

• Established a high-trust partnership with the firm’s outside compliance resources and ensured compliance responsibilities are consistently completed on time and at a high standard 

• Helped leadership identify operational gaps earlier and solve them before they become scale constraints 

• Elevated the business from “good people working hard” to a more durable, scalable operating environment 

Ideal Candidate Profile 

The ideal candidate is an experienced operator who knows how to build order inside a growing organization. They are practical, disciplined, and highly accountable. They can move fluidly between strategic thinking and execution detail. They understand that in a regulated business, operational excellence and compliance discipline must work together. 

This person does not need to come exclusively from an RIA background, but they do need to understand how to operate in a business where trust, process reliability, and regulatory discipline matter. They should bring the maturity to lead across functions, the confidence to improve accountability, and the humility to build systems that help others win. 

The strongest candidates will likely have experience in one or more of the following environments: 

• Wealth management / RIA 

• Financial services 

• Insurance 

• Banking 

• Accounting 

• Legal 

• Other regulated professional-services businesses 

Qualifications and Experience 

Required 

• 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 

Preferred 

• 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 

What This Role Is Not 

This role is not a back-office administrative manager, project coordinator, or narrow compliance specialist seat. 

It is also not a role for someone who only thrives inside large, mature, highly resourced corporate environments with established layers of support. 

This is a builder role for a senior leader who can help architect the next operating layer of the business. 

Why Join Hilltop 

Hilltop Wealth Advisors is building toward an ambitious future and is serious about becoming the kind of firm that can scale with excellence. 

This is an opportunity to join a leadership team that is actively investing in growth, improving its structure, and creating a stronger future for clients, advisors, and team members. The person in this role will have the chance to make a meaningful impact on how the firm operates, scales, and wins over the next several years. 

For the right candidate, this is not just an operations job. It is an opportunity to help build the next chapter of an ambitious, values-driven firm. 

Location 

This role is based in Chapel Hill, North Carolina. 

To Apply 

Please submit your resume along with a brief note sharing: 

• Why this role stands out to you 

• What kinds of businesses or environments you’ve helped scale 

• A specific example of an operational improvement you led that made a business materially stronger 

Compensation and Benefits  

• Competitive senior-level base salary ($200,000 - $250,000)  

• Participation in Hilltop’s firm-wide revenue incentive pool   

• Career path with increasing leadership responsibility and equity potential     

Hilltop offers a comprehensive benefits package including medical, dental, vision, and life insurance, a 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), and ongoing educational reimbursement opportunities.  

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