Executive Assistant - Strategic Support

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.

About Delegate Solutions

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.

About the Role

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.

Key Responsibilities

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.

What We’re Looking For

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

Required:

3+ years of experience in executive support, operations, project management, client success, business management, or a similar role.

Experience supporting executives, business owners, or senior leaders.

Experience managing multiple priorities, projects, or stakeholders.

Demonstrated ability to identify problems, recommend solutions, and move work forward independently.

Experience with process improvement, workflow development, project coordination, or operational support.

Exceptional written and verbal communication skills.

Strong critical thinking, organization, and time-management skills.

Ability to confidently communicate with senior-level clients.

Strong technology aptitude and ability to quickly learn new systems.

Experience working in a remote/virtual environment.

Proficiency with Microsoft 365 and/or Google Workspace.

Reliable high-speed internet and appropriate home-office equipment.

Availability Monday–Friday, 9 AM–5 PM ET.

Strongly preferred:

Experience supporting a CEO, founder, entrepreneur, or leadership team.

Operations or project management experience.

Experience managing multiple client accounts.

Experience creating or improving business processes.

Experience with Asana, ClickUp, or similar project management tools.

Experience using AI and automation to improve productivity and workflows.

You Will Thrive Here If You...

Naturally see what needs to happen within the work you support before someone asks.

Turn ambiguity into a clear plan.

Think in systems rather than individual tasks.

Bring solutions—not just problems.

Enjoy figuring out how work can be delegated, organized, and executed more effectively.

Can respectfully challenge a client or teammate when you see a better way to approach the work.

Are comfortable balancing proactive thinking with hands-on execution.

Take ownership of delegated work and support outcomes—not just assigned tasks.

Build strong, long-term relationships based on trust and reliability.

Enjoy working with entrepreneurs and growing businesses.

Our Core Values

Solutions-Focused Mindset – We take ownership, think critically, and bring solutions.

Enthusiasm for Excellence – We invest our time and energy in creating exceptional experiences for our clients.

Support and Respectfully Challenge One Another – We support our teammates while challenging one another to do our best work.

We Do What We Say – We create accountability, alignment, and results.

Professional Authenticity – We communicate openly, honestly, thoughtfully, and graciously.

Why Delegate?

We are a woman-owned, fully remote company that believes talented people should have the opportunity to do meaningful work, continue developing their skills, and make a measurable impact.

If you are looking for a role where you simply check tasks off a list, this isn’t it.

If you want to think, solve, organize, improve, proactively support, and make a meaningful difference for the leaders you work with , we’d love to hear from you.

Benefits: PTO, 401(k), Short-Term Disability, Long-Term Disability, Supplemental Life Insurance, 100% Work From Home

Delegate Solutions is an Equal Opportunity Employer.