Chief of Staff

Role Overview

The Chief of Staff is a strategic partner to the CEO and primary liaison between the CEO and the agency’s senior leadership team. This role translates the CEO’s vision into actionable outcomes, manages key operational and administrative needs of leadership, and helps keep internal infrastructure high-performing so the CEO and VP can focus on long-term strategy and growth.

Work setup: Remote company; role is hybrid with periodic travel to the Easton, MA office.

Responsibilities

• Directly manage four senior leaders (Creative Director, Director, Analytics, Sr. Technology and Operations Lead; also acting as Technical Product Owner).
• Serve as the translator of CEO directives, ensuring the leadership team has clear direction and the CEO receives timely updates with sufficient context.
• Handle people/administrative needs for the leadership tier, including:
  • performance management
  • coaching and development
  • goal setting
  • approval of schedules and requests
• Orchestrate cross-functional collaboration to remove silos and align workflows across departments.
• Define and monitor performance metrics for each direct report to ensure quality and on-time delivery.
• Lead resolution of operational roadblocks and leadership-tier conflict to maintain a collaborative culture.
• Partner with the CEO and VP to prepare for leadership meetings, ensuring agenda alignment and readiness.
• Maintain documentation of executive decisions and ensure follow-through on action items across departments.

Requirements

• Strong ability for strategic translation: turn abstract vision into measurable work streams.
• Executive diplomacy and consensus-building with high-level stakeholders.
• High organizational EQ for coaching and conflict mediation.
• Systems thinking to understand how changes cascade across the agency.
• High-stakes communication (verbal and written) with CEO-level authority and approachability.
• Decisive prioritization to filter operational noise from urgent vs. important.
• Discretion & integrity with confidential financial, personnel, and strategic information.
• Agility & resilience in a fast-paced, high-pressure environment.

Education & Experience

• Bachelor’s degree in business administration, management, or related field (required).
• MBA or equivalent (preferred).
• 7–10+ years of experience in agency leadership or senior management (minimum indicated).

Nice to Have / Additional Signals

• The role implies familiarity with agency operations across creative, analytics, technology/product ownership, and cross-functional execution.