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President / Chief of Staff

Local Candidates

Posted 9/10/25 Open Until Removed

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Position Title: President / Chief of Staff

Location: Stuart, Delray, Florida - Local candidates commutable to either office
Reports To: Owner / Chief Executive Officer
Employment Type: Full-Time, Exempt


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

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Position Summary:

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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.

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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.

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Primary Responsibilities:

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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.

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How to Apply:

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Please submit your resume and T-letter to paul@pmgsearch.com. Be sure to highlight relevant quantified experience to qualifications and primary responsibilities,

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