Executive Assistant To The Chief Operating Officer Jobs in Reston, VA

Executive Assistant to the CSO and COO

Location: Remote

Status: Full-Time

Reports to: Chief of Staff

Salary Range: $90,000 - $100,000

About Way to Win

Way to Win is a home for movement politics, donor organizing, and long-term power building. We work alongside grassroots organizations, donors, strategists, and partners to build durable power, advance narrative change, and support a multiracial democracy where all people can thrive.

Our work requires clarity, care, strong systems, and deep alignment across teams. We are looking for people who are values-aligned, collaborative, organized, and committed to building the infrastructure our movement needs to win.

Position Summary

The Executive Assistant to the Chief Operating Officer and Chief Strategy Officer serves as a critical operational and administrative partner to the executive team. As a team of three, this role supports the day-to-day functioning of the Office of the Executive Team and helps ensure that organizational priorities, cross-functional projects, internal communications, and executive workflows move forward with clarity, consistency, and follow-through.

This position extends beyond traditional executive assistance. The Executive Assistant will help manage complexity, anticipate needs, strengthen systems, and support the CSO and COO in leading across operations, human resources, finance, compliance, organizational culture, internal planning, and executive coordination.

The ideal candidate is highly organized, proactive, emotionally intelligent, detail-oriented, and an exceptional communicator. They bring strong judgment, discretion, and a solutions-oriented mindset. They are comfortable working in a fast-paced, mission-driven environment and using modern tools, including AI and productivity platforms, to improve how work gets done.

What You’ll Do

In this role, you will help the EVP/COO stay organized, prepared, and focused by managing key administrative, operational, and communication workflows. You will coordinate calendars, meetings, materials, follow-up, and cross-functional priorities while helping ensure that internal systems and executive operations run smoothly.

You will serve as a trusted partner who can anticipate needs, track details, surface risks, and move work forward with care and discretion. Your work will help create more clarity, consistency, and follow-through across political/program teams, operations, HR, finance, compliance, internal planning, and organizational infrastructure.

Key Responsibilities

Executive Administrative Support

• Provide high-level administrative support to the COO and CSO, including calendar management, meeting preparation, scheduling, travel coordination, expense support, and follow-up tracking.
• Manage the CSO and COO’s time and priorities with care, discretion, and strong attention to detail.
• Prepare agendas, briefing materials, documents, talking points, and follow-up notes for meetings, check-ins, and organizational priorities.
• Anticipate needs and help ensure the CSO and COO is prepared for internal and external engagements.

Operations & Organizational Coordination

• Support the CSO and COO in managing cross-functional workflows across political/program, communications, operations, HR, finance, compliance, systems, planning, and internal infrastructure.
• Track key deliverables, deadlines, decisions, and next steps across projects and leadership priorities.
• Help improve internal systems, templates, processes, and workflows that support organizational effectiveness.
• Partner with internal teams to ensure timely follow-through on operational priorities and organizational commitments.

Communications & Relationship Management

• Draft, edit, and prepare internal communications, meeting notes, follow-up messages, and other written materials on behalf of or in support of the EVP/COO.
• Serve as a thoughtful and professional point of coordination between the EVP/COO and internal stakeholders.
• Support clear, timely, and values-aligned communication across teams.
• Handle sensitive information with confidentiality, discretion, and sound judgment.

Executive Intelligence & Strategic Follow-Through

• Help the CSO and COO stay organized across competing priorities by tracking issues, decisions, risks, and follow-up needs.
• Identify gaps, surface potential concerns, and help ensure important details do not fall through the cracks.
• Support preparation for leadership meetings, staff planning, executive team needs, and internal decision-making spaces.
• Use judgment to distinguish between routine administrative needs and issues requiring executive attention.

Tools, Systems & Continuous Improvement

• Use project management, calendar, document, communication, and productivity tools to support efficient workflows.
• Comfortably use AI and modern productivity tools to draft, organize, summarize, synthesize, and improve work processes.
• Maintain organized files, trackers, templates, and documentation to support continuity and institutional knowledge.
• Recommend improvements to administrative and operational systems that strengthen the CSO and COO’s effectiveness and the organization’s overall workflow.

Qualifications

• 7+ years of strong experience providing executive-level administrative, operations, or project coordination support.
• Excellent writing, editing, communication, and follow-up skills.
• Strong calendar management, scheduling, meeting preparation, and organizational skills.
• Ability to manage multiple priorities, deadlines, and stakeholders with accuracy and care.
• High emotional intelligence, discretion, and sound judgment.
• Comfort working with confidential and sensitive information.
• Strong attention to detail and ability to anticipate needs.
• Comfort using technology, productivity tools, and AI-supported workflows.
• Experience in nonprofit, advocacy, political, philanthropic, movement, or mission-driven organizations is preferred.
• Commitment to Way to Win’s mission, values, and long-term political work.

Compensation & Benefits

Way to Win offers a competitive compensation and benefits package, including employer-paid medical, dental, and vision coverage; retirement contributions; paid time off; paid holidays and organizational closures; and additional benefits designed to support staff well-being.

Equal Opportunity Statement

Way to Win is an equal opportunity employer. We strongly encourage applications from people of color, women, LGBTQ+ people, people with disabilities, and people from other communities historically underrepresented in political, philanthropic, and nonprofit spaces.