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Executive Assistant

May 27, 2026

Watershed Advisors is looking for an Executive Assistant to join our Operations Team. As a fully remote organization, our team is set up to work collaboratively on projects across the country every day. This role can be based anywhere in the Eastern or Central time zones in the United States. <a href="https://watershed-advisors.com/" style="text-decoration:none;">About Watershed Advisors</a> Building on the deep public sector leadership experience of its team, Watershed Advisors supports governments to design, implement, and scale transformative education plans. We match proven education and workforce ideas, investors seeking social impact, and bold governmental leaders across the country. We then embed teams of experts within government agencies, coordinating multi-year efforts to implement, communicate, finance, and evaluate ideas to impact generations of American learners and job seekers in need of access and opportunity. THE OPPORTUNITYAt Watershed, the Executive Assistant is a core member of the team, who reports to the Senior Executive Assistant and works closely with up to 4 Managing Directors (MDs) to ensure they, and the teams they lead, are prepared and positioned to do their best work. The role requires someone who thinks ahead: anticipating what’s coming, owning solutions, and building systems. Primary responsibilities include: Calendar Support<ul><li style="list-style-type:disc;">Manage daily and weekly calendars for Managing Directors, including finding available time, prioritizing or adjusting meetings, and coordinating changes with internal team members and external contacts</li><li style="list-style-type:disc;">Communicate proactively with MDs around conflicts, trade-offs, and scheduling recommendations, and proposed solutions</li><li style="list-style-type:disc;">Identify and resolve scheduling conflicts for the week ahead; look 2–4 weeks out to flag potential conflicts or needs before they become urgent</li><li style="list-style-type:disc;">Schedule internal meetings with an eye toward balance and protecting focused work time</li><li style="list-style-type:disc;">Draft and send external scheduling correspondence that represents Watershed professionally</li><li style="list-style-type:disc;">Over time, manage agendas for recurring meetings that each Managing Director owns </li></ul> Travel and Events<ul><li style="list-style-type:disc;">Schedule and manage all travel details for the Managing Directors, including flights, hotels, and rental cars, with attention to preferences </li><li style="list-style-type:disc;">Provide real-time support when travel goes wrong — rebooking canceled flights, adjusting itineraries, and keeping the Managing Director informed with options </li><li style="list-style-type:disc;">Prepare, reconcile, and submit expense reports, working with the Operations team to resolve issues independently to the greatest extent possible</li></ul> Administrative & Strategic Support<ul><li style="list-style-type:disc;">Support the Managing Directors' external relationships by tracking follow-up commitments and flagging when outreach is due</li><li style="list-style-type:disc;">Partner with Business and Contract Managers to maintain business development and client relationship workflows, including CRM (e.g., HubSpot) data integrity, contact records, and visibility into pipeline activity, touchpoints, and follow-ups.</li><li style="list-style-type:disc;">Lead logistical coordination for coworking days and off-sites — shared schedules, room setup, A/V needs, supply coordination, and site visit details, in coordination with the Operations team </li><li style="list-style-type:disc;">Manage recurring administrative needs: conference registrations, gifts, contact tracking, and maintaining key documents (bios, headshots, resumes)</li><li style="list-style-type:disc;">Take on ad hoc strategic projects within the Operations Department or for Managing Directors </li></ul> Building Systems & Processes<ul><li style="list-style-type:disc;">Identify opportunities to improve team workflows by observing how tasks are being handled, spotting what works well, and suggesting new approaches to increase efficiency</li></ul><ul><li style="list-style-type:disc;">Build and refine repeatable systems for scheduling, communication, and client support, ensuring processes are consistent, reliable, and easy to share across the team.</li><li style="list-style-type:disc;">Proactively surface best practices and insights from across the Managing Directors, helping to create scalable methods that benefit everyone.</li></ul> SKILLS AND CHARACTERISTICSWe are looking for people who care deeply about education and its role in society, and who are eager to learn about approaches to improving the United States’ system of public education, from birth to postsecondary to the workforce. At Watershed, we work with a wide variety of clients and are seeking team members with diverse backgrounds and experiences. We encourage people of color, people with disabilities, immigrants, and others with diverse experiences to apply for this role. The Executive Assistant must have: <ul><li style="list-style-type:disc;">Anticipatory thinking, including the ability to identify potential issues before they arise, build proactive systems that solve common friction points, and act on behalf of the Managing Directors.</li><li style="list-style-type:disc;">Self-direction and ownership, including the ability to manage time and priorities independently, determine when to act and when to escalate, and stay productive without close supervision. When there is no immediate ask, the Executive Assistant looks ahead rather than waiting for the next request.</li><li style="list-style-type:disc;">Sound judgment under pressure, including the ability to triage competing urgent requests from Managing Directors, stay calm and organized when priorities shift quickly, and communicate clearly with all parties — even when a situation is still unfolding.</li><li style="list-style-type:disc;">Strong organizational skills, including time-management systems and the ability to manage multiple projects and priorities; familiarity with Microsoft Outlook and the ability to manage and maintain the Managing Directors’ busy schedules; familiarity with standard office platforms, such as Microsoft Office and Slack; and accurate record keeping, data management, and data entry skills.</li><li style="list-style-type:disc;">Strong written and verbal communication skills, including clear, professional correspondence with external partners on behalf of the Managing Directors; confident and constructive communication when something won't work, paired with a proposed alternative; and comfort operating as a representative of Watershed in a fully remote environment.</li><li style="list-style-type:disc;">Relationship-building skills, including the ability to learn and adapt to each Managing Director's working style, communication preferences, and priorities; to build trust through consistent follow-through over time; and to maintain positive relationships with individuals at all levels of the organization and with external stakeholders.</li><li style="list-style-type:disc;">Collegiality. At Watershed, we work collaboratively, engaging others in decisions, exchanging and challenging one another’s ideas and assumptions, and providing deep feedback on written materials. We expect every member of the team to embrace this approach and to operate with transparency, integrity, and a sense of humor. </li><li style="list-style-type:disc;">A personal commitment to social justice. At Watershed, we believe that systemic, longstanding bias within our nation’s institutions has too often harmed Black and brown Americans, low-income individuals and families, people with disabilities, and immigrants. Our work aims to build systems that serve all people and that bolster the prosperity and rights of those who have been excluded from educational and economic opportunity. </li></ul> EXPERIENCEThis role requires at least two years of experience in senior leader support, operations, or high-touch coordination roles — ideally supporting multiple senior leaders. We value the ability to translate adjacent experience into senior leader support, not just a traditional EA resume. COMPENSATIONThe salary for this position is $75,000 and includes a comprehensive benefits package, including medical, dental, vision, short-term disability, life, and AD&D insurance, paid sick and personal leave, and stipends for work-from-home expenses and professional development. All employees are eligible for end-of-year bonus pay. The final salary will be determined based on experience and qualifications. LOCATIONThis position is fully remote. Travel is required for 3-4 staff events per year. TO APPLYPlease submit your application through our careers page linked here. In addition to submitting your information and resume, please submit brief (no more than 1-2 paragraphs for each question) responses to the questions on the application. Your answers will help us to better understand your interests, experiences, and perspectives in addition to our review of your resume. EQUAL OPPORTUNITY EMPLOYERWatershed is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran status, or disability status.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...