About the role
100% Remote | U.S.
-Based | Independent Contractor
Location Requirements: This is a 1099 independent contractor role open to fully remote applicants residing anywhere in the United States, excluding California, Connecticut, Illinois, Massachusetts, New Jersey and New York due to local state regulatory compliance requirements.
About Delegate Solutions
Delegate Solutions helps entrepreneurial founders and CEOs lead with greater capacity through the right support, structure, and execution.
Since 2007, we’ve helped leaders get out of the weeds through experienced people and a proven methodology that increases executive effectiveness and leverage.
We’re building a bench of experienced professionals for our Fractional Chief of Staff services to support multiple entrepreneurial leaders.
About the Role
This is not a first Chief of Staff opportunity.
We’re seeking experienced Chiefs of Staff who know how to work closely with entrepreneurial founders and CEOs.
You move quickly without chaos, create structure without bureaucracy, respectfully challenge leaders, and anticipate their needs.
As a Fractional Chief of Staff, you’ll be a trusted thought partner and operator, helping founders focus, advance priorities, and strengthen follow-through.
This is an embedded fractional relationship, not occasional consulting. You’ll build the context and trust to exercise sound judgment while balancing multiple client engagements.
This role is 100% remote, supporting clients located across the U.S.
What You’ll Do
Your work may include:
- ·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
Your value comes from judgment, anticipation, communication, and influence—moving work forward without constant direction.
You Know Your Lane
Clients may already have an Executive Assistant, Integrator or COO, and leadership team.
You know how to work effectively alongside them.
You partner rather than compete, clarify ownership, and know when work belongs elsewhere.
You work closely with the executive without assuming administrative duties, company-wide operations, or another leader’s responsibilities.
Required Experience
To be considered, you must have:
- ·A 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
Executive Assistant experience alone—even at a senior level—is insufficient. Candidates must have performed the Chief of Staff function.
Experience supporting professional services businesses is strongly preferred.
Experience working within entrepreneurial operating systems such as EOS is a plus.
Who We’re Looking For
You may be a strong fit if:
- ·You’re highly anticipatory. You notice patterns, see around corners, and think ahead about what your executive will need.
- ·You…