Remotehey

About Our Client

The American economy presents challenges for many working adults who do not earn a living wage. These talented individuals often have limited options for advancement: traditional college is lengthy and costly, full-time boot camps lack flexibility, and online courses may not provide sufficient structure or support to transition into a new career. This situation can leave skilled workers, disproportionately people of color and women, in low-wage roles without a clear path to a better future for themselves and their families.

Our client creates pathways to family-sustaining careers for Americans facing these challenges. Its fast, flexible solutions are designed for working adults. The process begins by analyzing job market data to identify in-demand, high-paying tech careers. Then, in partnership with industry-recognized organizations, it trains individuals for these roles through part-time programs that blend flexible online learning with expert coaching. Finally, it supports learners in their job search, connecting them with a wide range of employers to secure higher-earning, family-sustaining jobs. The mission is to build a scalable pathway for workers to achieve middle-class status through merit, not financial means.

Note: While the organization generally operates on a four-day workweek, this role requires a five-day schedule (Monday–Friday) due to the nature of executive support.

About The Role

The primary objective of the Executive Assistant to the Co-CEOs is to maximize the efficiency and effectiveness of the Co-CEOs. This involves managing complex calendars, coordinating executive travel, streamlining operations, and acting as a trusted liaison between the Co-CEOs and both internal and external stakeholders.

This role reports directly to the Chief of Staff and works primarily with the Co-CEOs. The position offers the potential for growth into expanded responsibilities over time, including support for strategic projects, board coordination, and executive communications.

Key Responsibilities

Executive Calendar & Schedule Management (50%)

• Manage complex calendars for two Co-CEOs, scheduling meetings with critical stakeholders, typically within 24 hours of request
• Proactively identify and resolve scheduling conflicts, prioritizing meetings aligned with CEO goals and organizational priorities
• Coordinate across both Co-CEOs' schedules to ensure alignment and efficiency
• Prepare daily/weekly schedule briefings with context, materials, and priorities
• Monitor and respond to scheduling requests with urgency when needed (note: while responses outside business hours are appreciated for urgent matters, they are not required)

Travel & Logistics Coordination (20%)

• Plan and coordinate executive travel, including flights, accommodations, ground transportation, and detailed itineraries
• Manage travel logistics for conferences, board meetings, donor visits, and strategic partner meetings
• Handle expense reconciliation and travel reimbursements
• Anticipate travel needs and prepare travel-related briefing materials

Communication & Stakeholder Management (20%)

• Draft and edit emails, correspondence, meeting agendas, and post-meeting action items on behalf of the Co-CEOs
• Serve as a professional point of contact for internal teams, board members, partners, and external stakeholders
• Manage the Co-CEOs' inboxes, flagging priority items and drafting responses as appropriate
• Maintain discretion with sensitive and confidential information

Operational Support & Project Coordination (10%)

• Streamline workflows and systems to align with CEO priorities and deadlines
• Coordinate logistics for leadership meetings, team offsites, and organizational events
• Support cross-functional initiatives and strategic projects as needed
• Maintain organized systems for tracking action items, deadlines, and follow-ups
• Assist with Board coordination, including meeting minutes and follow-up actions (as role expands)

Skills & Competencies

Our client recognizes that individuals from underrepresented backgrounds may hesitate to apply if they do not meet every listed qualification. Applicants are encouraged to apply if their background demonstrates the required skills and competencies, as unique skills, experiences, and perspectives are valued.

Essential Requirements for all roles:

• Commitment to the organization's mission to create pathways to family-sustaining careers, break the poverty cycle, and foster upward mobility for low-wage workers
• Demonstrated history of embodying the organization's values, which inform its work and drive its culture
• Shared sense of responsibility and ownership for collective work in making a positive impact on the community supported, aligning with the value of Win & Lose Together
• Commitment to continuous learning and growth in advancing inclusive excellence and closing gaps across lines of difference
• Passion for fostering a workplace culture that embraces and values individual differences, in alignment with the core value of inclusivity

Essential Requirements for this role:

Executive Support & Calendar Management

• Experience as an Executive Assistant or in a similar high-level administrative role
• Proven expertise managing complex calendars for senior executives, with the ability to prioritize and coordinate across multiple stakeholders
• Track record of anticipating needs and proactively solving problems before they arise

Communication & Stakeholder Management

• Exceptional written and verbal communication skills, with the ability to draft professional correspondence on behalf of executives
• Strong interpersonal skills and the ability to build positive relationships with internal and external stakeholders at all levels
• Ability to serve as a professional liaison between executives and board members, partners, and teams

Organization & Project Coordination

• Strong organizational skills with the ability to manage multiple priorities simultaneously in a fast-paced environment
• Experience coordinating complex travel logistics, including international travel arrangements
• Ability to streamline workflows and implement systems to improve executive efficiency

Technical Proficiency & Adaptability

• Proficiency with Google Workspace, Slack, Zoom, and other collaboration tools
• Comfort working in a fully remote environment with a distributed team
• Ability to learn new tools and systems quickly

Discretion & Professionalism

• Demonstrated ability to handle sensitive and confidential information with the utmost discretion
• Sound judgment in prioritizing issues and knowing when to escalate
• Flexibility to respond to urgent matters outside standard business hours when needed

Preferred Qualifications

• Experience supporting C-suite executives at a nonprofit or mission-driven organization
• Experience in a startup or high-growth environment
• Background in education, workforce development, or social impact sectors
• Experience supporting large-scale events or offsites

Additional Information

• This position is full-time: Monday-Friday, 40-50 hours/week
• Location: Remote
• Salary: $100,000

Perks and Benefits

The organization provides the following perks and benefits:

• Medical, Dental, and Vision insurance (100% Paid Employee Only Coverage)
• Flexible Spending Account and Health Savings Account
• Dependent care Flexible Spending Account
• Health Reimbursement Account fully funded by the organization
• Education & personal development reimbursement
• Catalog of courses for professional learning and development
• Short and long-term disability
• Unlimited vacation (after a 90-day introductory period)
• Paid Parental Leave and Adoption benefits (after 1 year of employment)
• 11 federally recognized holidays
• 2 week holiday office closure in December/January
• 401(k) retirement plan with automatic organization contribution
• Wellness Benefits/Wellness Resources
• Discount perks at work program
• Phone/technology stipend
• Home office setup stipend
• Affinity groups and community building via virtual, in-person, and/or regional meetups

Remote Work & Sponsorship

Candidates must reside within the 50 states or District of Columbia and have full authorization to work in the 50 U.S. states & the District of Columbia. International work abroad, including U.S. territories (Puerto Rico, Guam, U.S. Virgin Islands, and other islands are excluded). The organization does not offer employment visa sponsorship.

Note:

“We are not the EOR (Employer of Record) for this position. Our role in this specific opportunity is to connect outstanding candidates with a top-tier employer. Swooped helps candidates around the world to discover and stay focused on the jobs they want until they can complete a full application in the hiring company career page/ATS.”