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Delegate Solutions

Fractional Chief of Staff

Delegate Solutions

. Serve as a trusted thought partner to a founder or CEO .

Posted 9/25/2026contractRemote • United StatesLeadWebsite

About the role

Key responsibilities & impact
  • Serve as a trusted thought partner to a founder or CEO
  • Help executives maintain focus on their highest-value priorities
  • Translate ideas and decisions into clear action and ownership
  • Drive follow-through on strategic priorities and initiatives
  • Prepare executives for important meetings, conversations, and decisions
  • Anticipate needs, flag risks early, and propose solutions
  • Connect dots across priorities, people, and initiatives
  • Coordinate with leaders and key stakeholders to keep work moving
  • Improve clarity, communication, and accountability around executive priorities
  • Protect the executive’s time by focusing their involvement where it adds the most value
  • Work effectively alongside Executive Assistants, Integrators/COOs, and leadership teams
  • Partner rather than compete, clarify ownership, and determine when work belongs elsewhere
  • Support multiple fractional client engagements based on experience, strengths, availability, and fit
  • Deliver work within Delegate Solutions’ proprietary executive-leverage methodology

Requirements

What you’ll need
  • Minimum of 2 years of direct Chief of Staff experience; 3+ years preferred
  • Meaningful experience supporting a founder or CEO in an entrepreneurial, founder-led organization
  • Experience operating at the intersection of strategy, communication, prioritization, and execution
  • Experience driving priorities across teams without relying on formal authority
  • Strong executive-level written and verbal communication skills
  • Demonstrated judgment, discretion, and ability to navigate ambiguity
  • Experience succeeding in fast-moving environments where priorities evolve
  • Candidates must have performed the Chief of Staff function; Executive Assistant experience alone is insufficient
  • Experience supporting professional services businesses strongly preferred
  • Experience with entrepreneurial operating systems such as EOS® is a plus
  • Ability to balance multiple fractional clients with responsiveness, communication, and follow-through
  • Ability to work remotely and build strong executive relationships virtually
  • Applicants must reside in the United States, excluding California, Connecticut, Illinois, Massachusetts, New Jersey, and New York
  • Must be able to work as a 1099 independent contractor

Benefits

Comp & perks
  • 100% remote work
  • Independent contractor engagement
  • Training in Delegate Solutions’ proprietary executive-leverage methodology
  • Support from systems and infrastructure behind client engagements
  • Access to Delegate’s methodology, frameworks, and tools for authorized client engagements
  • Opportunity to build a portfolio career across multiple entrepreneurial leaders
  • Flexible client assignments based on experience, strengths, availability, and fit