Seeking a President / Chief of Staff for a South Florida Multi-Entity Portfolio

Paul Mitchell

Position Title: President / Chief of Staff

Location: Stuart, Delray, Florida

Reports To: Owner / Chief Executive Officer

Employment Type: Full-Time, Exempt

Compensation: Competitive salary commensurate with experience, plus performance-based incentives and benefits

Position Summary:

We are seeking a highly accomplished and strategically minded President / Chief of Staff to provide executive oversight and operational leadership across a portfolio of three distinct business entities: a personal injury law firm, a real estate & land investment firm, and a high growth roofing and construction company.

This individual will serve as a trusted partner to the Owner/CEO and assume day-to-day responsibility for ensuring that each entity operates efficiently, profitably, and in alignment with long-term strategic objectives. The ideal candidate brings a track record of executive leadership across multiple industries, with the ability to drive performance while maintaining operational discipline and fostering organizational cohesion.

Primary Responsibilities:

Executive Leadership & Strategic Alignment

• Collaborate closely with the Owner/CEO to develop, refine, and execute strategic plans across all entities.

• Provide centralized leadership while respecting the distinct operational needs and regulatory environments of each business.

• Drive cross-functional alignment, organizational effectiveness, and scalable growth strategies.

  
  

Operational Oversight

• Direct and oversee daily operations across the law firm, roofing company, and real estate investment business.

• Establish, monitor, and refine operational procedures, internal controls, and performance metrics.

• Ensure operational consistency, quality assurance, and regulatory compliance across all entities.

Financial Management

• Provide executive oversight of budgeting, forecasting, and financial reporting functions.

• Analyze financial performance and identify opportunities to improve profitability and operational efficiency.

• Work in close partnership with internal and external financial teams to ensure fiscal responsibility and accurate reporting.

Personnel Management & Organizational Development

• Lead, mentor, and manage senior-level staff and department heads across all business units.

• Drive talent acquisition and retention strategies that support organizational growth.

• Promote a culture of accountability, professionalism, and continuous improvement.

Project & Initiative Execution

• Manage special initiatives on behalf of the CEO, including business development, market expansion, or operational integration projects.

• Serve as a strategic liaison between the CEO and key stakeholders, ensuring high-priority objectives are achieved efficiently and effectively.

• Monitor and prioritize key deliverables across multiple time zones and business verticals.

Regulatory & Risk Management

• Ensure all businesses operate in full compliance with applicable laws, industry standards, and licensing requirements.

• Oversee risk management policies and procedures, including insurance, legal matters, and vendor/partner relationships.

Qualifications:

• Minimum of 8–10 years of executive-level experience in a multi-entity or multi-industry environment.

• Demonstrated success in overseeing operations, finance, and strategic planning across varied business sectors.

• Experience within one or more of the following industries is strongly preferred: legal services, construction or roofing, real estate investment or professional services.

• Bachelor’s degree required; MBA, JD, or equivalent advanced degree preferred.

• Exceptional interpersonal, organizational, and leadership skills.

• High level of discretion, integrity, acumen, and executive presence.

Core Competencies:

• Strategic Thinking and Execution

• Financial and Operational Acumen

• Cross-Industry Adaptability

• Leadership and Talent Development

• High-Level Communication and Diplomacy

• Results-Oriented and Analytical Decision-Making

Opportunity:

This role presents a unique opportunity to lead and influence a diverse group of businesses under a single ownership structure. The successful candidate will play a pivotal role in shaping the direction and future success of each entity while working directly with a founder who values strategic insight, organization, operational excellence, and long-term growth.

How to Apply:

Please submit your resume and T-Cover Letter to paul@pmgsearch.com.