Executive Assistant - Strategic

All positions are 100% remote | Monday–Friday, 9 AM–5 PM ET

We are currently hiring in the US, with the exception of Alaska, California, Colorado, the District of Columbia, Hawaii, Illinois, Iowa, Maine, Massachusetts, Michigan, Minnesota, Montana, New Hampshire, New York, North Dakota, Ohio, Oregon, Rhode Island, South Dakota, Washington State, and Puerto Rico.

This role is open only to candidates who are authorized to work in the United States and whose primary work location will be within the United States.

Delegate Solutions provides Fractional Executive Enablement to entrepreneurs, CEOs, and leadership teams. We combine proactive executive support, thoughtful execution, accountability, and process improvement to help leaders get the right work off their plate and create more capacity for growth.

We are looking for an experienced Strategist to join our team and serve as a trusted executive support partner to our clients.

This is a senior, consultative executive support role—not a task-based administrative position. Our Strategists are proactive thinkers, problem solvers, client partners, and project coordinators who are also highly capable of executing administrative work when needed.

As a Strategist, you will manage a portfolio of client relationships and work alongside an Implementer to help clients delegate more effectively, strengthen their executive support systems, and keep important work moving.

You will get to know each client’s business, priorities, challenges, and working style, then proactively identify opportunities to improve how work is delegated, organized, coordinated, and executed.

You won’t simply wait for clients to tell you what to do. You’ll identify opportunities within their executive support needs, make recommendations, create a plan, coordinate execution, and make sure delegated work gets done.

• Serve as a trusted, proactive executive support partner to business owners and executives.
• Lead weekly client calls to review delegated work, support priorities, upcoming needs, and follow-through.
• Create and maintain client Action Plans and translate executive support needs into clear, actionable priorities.
• Partner with the Implementer to plan, delegate, and coordinate client work.
• Proactively identify pain points, bottlenecks, and opportunities to create greater leverage for the executive.
• Design and improve executive support systems, processes, and workflows that save clients time and reduce unnecessary work.
• Look for opportunities to leverage AI, automation, and technology to improve efficiency.
• Coordinate executive support projects, deadlines, recurring workflows, and delegated priorities.
• Anticipate upcoming needs and proactively recommend ways Delegate can provide greater support.
• Monitor client retainer usage and ensure hours are being used strategically and efficiently.
• Communicate proactively with clients and teammates and address issues before they become problems.
• Ensure work is completed accurately, on time, and to Delegate’s standards.
• Execute administrative and project-based work when appropriate, including calendar and inbox management, scheduling, research, travel logistics, communications, and other executive support.
• Maintain client documentation, systems, and processes.
• Represent Delegate Solutions’ brand and values in every client interaction.

We are looking for someone who has already demonstrated the ability to operate with judgment, independence, professionalism, and proactive thinking.

• 3+ years of experience in executive support, operations, project management, client success, business management, or a similar role.
• Experience supporting executives, business owners, or…