Executive Assistant to CSO and COO - Remote

About Way to Win

Way to Win is a proactive organization focused on advancing movement politics, organizing donors, and fostering long-term political power. Collaborating with grassroots groups, donors, and partners, the organization works towards building durable power, encouraging narrative change, and supporting a multiracial democracy that benefits all individuals. Their approach highlights clarity, care, strong systems, and deep team alignment to promote impactful advocacy, equity, and justice.

Role Overview

The Executive Assistant supports the Chief Strategy Officer (CSO) and Chief Operating Officer (COO) by ensuring smooth executive team operations. This key role combines operational and administrative tasks, facilitating priorities, projects, communications, and workflows across functions. Responsibilities extend beyond routine administration to include managing complexity, anticipating needs, and supporting areas such as operations, HR, finance, compliance, organizational culture, and internal planning. Ideal candidates are organized, proactive, emotionally intelligent, excellent communicators, and adept at using technology and AI tools to enhance productivity.

Key Responsibilities

• Deliver executive-level admin support including calendar oversight, meeting prep, travel arrangements, expense management, and follow-up coordination.
• Discreetly manage executive team priorities and time effectively.
• Develop agendas, briefing documents, talking points, and follow-up notes for meetings and initiatives.
• Anticipate executive needs for thorough preparation for engagements.
• Facilitate cross-departmental workflows involving politics, communications, operations, HR, finance, and compliance.
• Monitor deliverables, deadlines, decisions, ensuring timely completion.
• Enhance internal systems, templates, and workflows to boost organizational efficiency.
• Draft, edit, and prepare internal communication and documentation.
• Act as liaison between executives and stakeholders, managing relationships with professionalism and confidentiality.
• Track issues, decisions, risks, and follow-ups to support strategic initiatives.
• Identify workflow gaps, highlight potential issues, and assist in leadership meeting prep.
• Use project management, calendaring, document, and communication tools for efficient operations.
• Leverage AI and modern productivity platforms to improve processes and systems.
• Maintain organized records, trackers, templates, and documentation to preserve institutional knowledge.
• Recommend and apply improvements to administrative and operational systems.

Qualifications

• More than 7 years of experience providing executive-level administrative, operational, or project support.
• Strong written communication, editing, and interpersonal skills.
• Expertise in calendar management and scheduling.
• Outstanding organizational abilities with exceptional attention to detail.
• Capability to handle multiple priorities and meet deadlines effectively.
• High emotional intelligence, discretion, and sound judgment.
• Experience handling sensitive and confidential information.
• Familiarity with technology, productivity applications, and AI-enhanced workflows.
• Background in nonprofit, advocacy, political, philanthropic, or mission-driven work is preferred.
• Alignment with Way to Win’s mission, values, and political objectives.

Benefits

• Competitive salary range between $90,000 and $100,000 annually.
• Employer-paid medical, dental, and vision insurance coverage.
• Retirement plan with employer contributions.
• Paid holidays and time off, including organizational closures.
• Supportive work culture prioritizing staff well-being and professional growth.
• Opportunity to work within an organization committed to social justice and equity.

Equal Opportunity

Way to Win is committed to equal employment opportunities and encourages applicants from all backgrounds, including individuals of color, women, LGBTQ+ people, those with disabilities, and other underrepresented groups in political and nonprofit sectors. The organization fosters an inclusive environment valuing diverse perspectives and experiences.