Chief of Staff

Chief of Staff

Location: Remote/Hybrid (East Coast/Washington, DC area preferred for periodic in-person meetings)  

Reports to: Managing Partner / Chief Operating Officer  

About the Role  

We are seeking a highly capable Chief of Staff to support the Managing Partner & COO across a portfolio of three companies—one agency/service business and two technology-focused subsidiaries (one a Data-as-a-Service provider and the other a vertical CRM SaaS platform). The COO oversees operations and product development across all three entities and is seeking a strategic partner and proxy who can ensure initiatives move forward, management teams are aligned, and execution is seamless.  

The Chief of Staff will act as an operational and strategic extension of the MP/COO—providing leadership, coordination, and project management across the group. This role requires strong business judgment, exceptional project management skills, and the ability to manage both people and processes across different business models.  

Why Join Us  

This is a unique opportunity for a seasoned professional who is a self-starter and thrives in an entrepreneurial environment. All three companies in the portfolio are profitable and experiencing rapid growth, creating a dynamic atmosphere where no two days are the same. The right candidate will enjoy working in a fast-paced, rapidly evolving organization with direct exposure to senior leadership and the chance to make an outsized impact across multiple businesses.  

Key Responsibilities  

Strategic Execution & Proxy Leadership  

• Serve as a trusted advisor and proxy for the MP/COO in meetings and decision-making across all three companies.  
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• Translate executive vision and strategy into clear action plans and ensure accountability within management teams.  
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• Anticipate challenges and proactively address roadblocks before they escalate.  

Operational Management  

• Partner with leadership teams in the service-based company to streamline workflows, optimize resource allocation, and ensure efficient delivery of client services.  
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• Support technology development efforts in the data and software subsidiaries, overseeing timelines, priorities, and cross-functional collaboration.  
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• Drive alignment across business units by tracking KPIs, managing reporting, and ensuring initiatives stay on track.  

Project Management & Technology Oversight  

• Lead complex projects, particularly in software and data product development, ensuring milestones are achieved on schedule.  
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• Implement project management frameworks and tools to improve visibility and accountability across teams.  
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• Drive cross-functional coordination between engineering, product, and business operations.  

Leadership Support & Communication  

• Act as a central hub for communication between the MP/COO and the three management teams.  
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• Ensure leaders have clarity on objectives, priorities, and deliverables.  
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• Synthesize insights from across the organization and provide the MP/COO with actionable recommendations.  
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• Coordinate and liaise with the Holding Company CEO and the MP/COO to ensure alignment on priorities, strategy, and execution.  

Qualifications  

• 10+ years of progressive business and operational experience, ideally spanning both services and technology environments.  
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• Strong background in project management (certification such as PMP or Agile/Scrum a plus, but equivalent experience also acceptable).  
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• Proven ability to manage multiple stakeholders and priorities across diverse business models.  
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• Excellent communication, relationship-building, and executive presence.  
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• Demonstrated success in acting as a proxy or trusted advisor to senior executives.  
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• Strong analytical and problem-solving skills with a bias toward execution.  
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• Comfortable in a remote-first environment; ideally based on the East Coast (Washington, DC area preferred) with the ability to travel for periodic in-person meetings.  

What We Offer  

• Opportunity to work at the intersection of services, data, and software in a fast-paced, entrepreneurial environment.  
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• Direct exposure to executive decision-making and company-building at scale.  
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• Competitive compensation and benefits package.  
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• Flexibility of a remote role with the benefit of occasional in-person collaboration.  
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• Significant opportunity for career growth, with all three companies profitable and rapidly expanding.