Watershed Advisors is looking for a Senior 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 United States.

About Watershed Advisors

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 OPPORTUNITY
The Senior Executive Assistant is a core member of the Operations Team and serves as the primary Executive Assistant to the CEO, President, and COO, providing high-touch, proactive, and highly confidential support. In addition, the Senior Executive Assistant will manage and develop two Executive Assistants, establishing consistent standards, systems, and executive-ready coverage across the leadership team. This includes owning and executing the performance management review process for the two Executive Assistants (goal setting, mid-year and end-of-year reviews, calibration inputs as applicable, and documentation). Primary responsibilities include:

Calendar Support

Own complex calendar management and scheduling strategy for the CEO, President, and COO, including prioritization, conflict resolution, and proactive planning in a fast-paced environment.
Establish and enforce scheduling norms (holds, buffers, prep time, internal/external meeting rules) to protect executive focus time and maximize effectiveness.
Ensure leaders are prepared with agendas, context, and pre-reads for high-stakes meetings; coordinate with internal stakeholders to drive clarity and outcomes.

Travel and Events

Plan and manage all travel logistics for the CEO, President, and COO (client meetings, conferences, internal meetings), including complex itineraries and contingency planning.
Prepare, reconcile, and submit expense reports; oversee quality and timeliness across the Executive Assistant team.

People Management

Manage and coach two Executive Assistants, including owning the performance management review process (goal setting, ongoing feedback, mid-year and end-of-year reviews, and documentation) and supporting development planning.
Design and maintain a clear coverage model across the Executive Assistant team (who owns which leaders, back-up coverage, and escalation pathways).
Delegate and triage requests appropriately to maintain high service levels for the CEO, President, and COO.
Serve as the escalation point for complex scheduling/travel issues and sensitive communications

Building Systems & Processes

Take on ad hoc strategic projects within the Operations Team.
Identify opportunities to improve workflows by observing how tasks are handled, spotting what works well, and implementing improvements.
Build and refine repeatable systems for scheduling, communication, travel, and client support that are consistent, reliable, and easy to share across the team.
Proactively surface best practices and insights across leaders and codify them into playbooks, templates, and operating rhythms.
Use judgment and data to continuously improve service quality (e.g., tracking common failure points, response-time norms, recurring calendar conflicts).

SKILLS AND CHARACTERISTICS
We 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 Senior Executive Assistant must have:

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 Executive Team’s busy schedules; familiarity with standard office platforms, such as Microsoft Office and Slack; and accurate record keeping, data management, and data entry skills.
Communications skills, including the ability to communicate clearly and appropriately with staff and external stakeholders at all levels; excellent written communication for correspondence; strong interpersonal skills; professional and courteous demeanor; effective office and phone etiquette; and the ability to defuse tense situations.
People leadership skills, including the ability to manage, coach, and develop two Executive Assistants; set clear expectations and standards; delegate effectively and maintain appropriate oversight; and establish a reliable coverage model (backup coverage and escalation pathways) to ensure consistent, high-quality support for the CEO, President and COO.
General professional skills, including accuracy and attention to detail, the ability to work well under pressure and navigate multiple deadlines, a proactive approach to problem-solving and process improvement, experience in developing and refining internal processes, and sound judgment in handling confidential information with discretion and professionalism.
Relationship-building skills, including the ability to build and maintain positive relationships with individuals at all levels of the organization and with a diverse group of external stakeholders.
An entrepreneurial mindset that leads to flexibility and creativity in pursuit of goals and resilience in the face of setbacks.
Independent decision-making skills, including the ability to take initiative within established direction, exercise sound judgment, and make decisions that benefit the group as a whole.
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.
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.

EXPERIENCE
This role requires 5-7 years of experience supporting senior executives, with demonstrated success supporting C-suite executives in complex, high-volume environments. People management experience strongly preferred (or clear evidence of leading/mentoring other administrative professionals).

COMPENSATION
The salary for this position is $80,000 - $85,000 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.

LOCATION
This position is fully remote. Travel is required for 3-4 staff events per year.

TO APPLY
Please 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 EMPLOYER
Watershed 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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Watershed Advisors

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Senior Executive Assistant