Chief Operating Officer/Chief Compliance Officer

Key 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

Qualifications and Experience

• 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