Fractional Chief of Staff - Independent Contractor

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 understand entrepreneurial founders: fast pace, ambiguity, shifting priorities, and businesses still reliant on founder judgment.
• You create clarity without bureaucracy.
• You exercise excellent judgment. You know when to act, when to influence, when to challenge, and when to escalate.
• You respectfully challenge leaders. You’re a thought partner, not an order taker.
• You connect dots quickly. You naturally see dependencies, risks, and implications.
• You influence without authority. You can move work and people forward through credibility, relationships, and communication.
• You build trust quickly through discretion, context, chemistry, and credibility.
• You can move between strategy and execution.
• You collaborate well with EAs, Integrators/COOs, and leadership teams and understand the distinct role each plays.
• You thrive working remotely. You communicate proactively and know how to build strong executive relationships virtually.
• You build close client relationships while maintaining boundaries across multiple engagements.

The Fractional Opportunity

Delegate Fractional Chiefs of Staff work as independent contractors supporting client engagements based on their experience, strengths, availability, and fit.

This is not a 9-to-5 or single-executive role. You must balance multiple fractional clients with responsiveness, communication, and follow-through.

Client assignments and the number of active engagements may vary and are not guaranteed.

Our Methodology & Support

Fractional Chiefs of Staff are trained in Delegate Solutions’ proprietary executive-leverage methodology and supported by the systems and infrastructure behind our client engagements.

You’ll bring your own experience, perspective, and judgment while delivering work within the Delegate approach.

Delegate’s proprietary methodology, training, frameworks, tools, and intellectual property are reserved for authorized Delegate client engagements.

Our Core Values

The people who thrive at Delegate share a few important characteristics:

• Innate Spirit of Helping Others
  We intentionally look for ways to make things better for the people around us.
• Enthusiasm for Excellence
  We care deeply about the quality of our work and the outcomes we create.
• Support and Respectfully Challenge One Another
  We believe great partnership requires both support and the willingness to speak up.
• We Do What We Say
  Accountability, reliability, and follow-through matter.
• Professional Authenticity
  We communicate openly, thoughtfully, honestly, and graciously.

The Right Person for This Opportunity

You may already be an experienced Chief of Staff who loves the work but wants to apply your experience across multiple entrepreneurial leaders.

You may be looking for a portfolio career that allows you to remain close to founders and CEOs while working within a proven firm and methodology.

If you have already successfully served as a Chief of Staff, understand entrepreneurial founders, know how to operate confidently alongside an EA, Integrator/COO, and leadership team, and are energized by helping leaders gain clarity, capacity, and momentum, we’d love to hear from you.

Compensation is project-based on total contract value

Delegate Solutions is an Equal Opportunity Employer and contracting partner.