Summary
We’re looking for an Executive Assistant (EA) to support three CEOs leading growing, mission-driven organizations. This role is central to how we work—and it’s part of a shared services model we’re intentionally testing and learning from. Our hope is that, if done well, this model can offer a thoughtful, sustainable way for organizations to access high-level executive support.
The three CEOs you’ll support are deeply collaborative, socially invested, and actively building organizations that aim to have real impact. We’re looking for a partner-minded EA who can provide the kind of high-trust, high-level support that allows us to operate at the next level.
Day to day, this role keeps work moving and leaders focused—managing calendars and inboxes, coordinating logistics, tracking commitments, and ensuring follow-through. But it goes beyond task management. We’re looking for someone who owns the thinking behind the work: anticipating needs, noticing patterns, improving systems, and making thoughtful decisions about priorities and flow.
This is a shared services role, which means you’ll be technically employed by Endeavor TBD while supporting three leaders across related organizations. You’ll balance time and priorities across them, build trusted relationships with each, and help create consistency across how work gets done.
The right person enjoys staying a step ahead, bringing order to complexity, and taking responsibility for outcomes—not just activities. The work blends strong administrative skills with judgment, planning, and proactive coordination, and it’s well-suited for someone who likes being relied on and trusted.
About Endeavor TBD, Durant Bailey, and The Equity Brain Trust
The Executive Assistant will support the CEO’s of three businesses/organizations through a coordinated, clearly prioritized shared-services model. Each organization is outlined below:
- Endeavor TBD (www.endeavortbd.com) is the operations firm for social enterprise.® E.TBD works with mission-driven organizations and businesses on implementation. The firm provides implementation support, fractional operator staffing, full-time operator search, and ops training for nonprofits and small businesses.
- Durant Bailey (www.durantbailey.com) is a financial consulting firm that supports organizations and leaders through growth, partnerships, and strategic initiatives, with a focus on execution, relationships, and operational clarity.
- The Equity Brain Trust (TEBT) is a data firm that works with economic developers to drive equitable growth. TEBT utilizes strategy and design, data capacity-building, and software solutions to collect, manage, and visualize data for continuous improvement and results.
About the Executive Assistant Role
In this role, the Executive Assistant is not only responsible for managing tasks and logistics, but for owning how executive support functions day to day. This includes thinking ahead, planning proactively, making informed judgment calls, and continuously improving how systems, communication, and coordination work across the three executives. We’re looking for someone who takes responsibility for outcomes, not just assignments.
The following are core responsibilities:
Executive Inbox & Calendar Management
- Manage and triage executive inboxes with discretion and judgment
- Draft and send routine responses using approved language and templates
- Schedule, reschedule, and confirm meetings across multiple calendars
- Prepare daily or weekly calendar look-aheads and flag conflicts
- Coordinate travel logistics when needed
Meeting & Communication Logistics
- Coordinate meeting logistics (Zoom links, agendas, materials)
- Take notes on selected meetings (e.g., business development, planning)
- Send follow-ups, summaries, and action items
- Track next steps so conversations turn into movement
Administrative Business Operations
- Prepare and submit invoices using existing templates
- Track invoice status and follow up as needed
- Assist with contract and scope submissions (admin side only)
- Maintain organized records for financial and administrative documents
CRM, Pipeline & Follow-Up Support
- Maintain lead trackers or CRM systems (status updates, notes, reminders)
- Flag stalled follow-ups or overdue actions
- Prepare daily or weekly follow-up reminders for each CEO
- Track proposal deadlines and key dates
Internal Organization & Systems Support
- Maintain shared folders, templates, SOPs, and playbooks
- Keep internal trackers, to-do lists, and Gantt charts up to date
- Support timesheet reminders and basic internal reporting
- Create a structure where needed
Intern Support
- Coordinate logistics for interns or entry-level hires
- Schedule interviews and send communications
- Track applications and onboarding steps
- Support orientations and surveys
Marketing & Communications Support
- Schedule LinkedIn posts, newsletters, or announcements
- Coordinate webinar or event logistics when needed
- Pull engagement metrics (views, clicks, replies)
- Upload and organize marketing assets
Special Projects
- Support clearly defined, time-limited projects
- Example: intern onboarding coordination, document cleanup, event prep
What Doing Well Looks Like
- Executives feel less reactive and more focused
- Calendars run smoothly and meetings are prepared and followed up
- Inboxes are organized, prioritized, and never overwhelming
- Follow-ups, deadlines, and commitments are consistently tracked
- Systems are tidy, searchable, and up to date
- Work moves forward with clarity and follow-through, without executives needing to closely monitor tasks
- The EA communicates clearly; asks keen, clarifying questions; and escalates appropriately
Strong Candidates Probably
- Love creating order and keeping systems clean
- Enjoy implementing and following through
- Are energized (not intimidated) by supporting multiple leaders
- Enjoy implementing, following through, and taking responsibility for how work gets done
Position Type and Compensation
This is a full-time, exempt position with a salary of up to $65,000/yr, commensurate with experience and qualifications. Benefits include Medical, Dental, Vision, Paid Vacation, and Paid Holidays.
Expected Work Commitment / Work Location
Standard hours are Monday–Friday, 9:00 a.m.–5:00 p.m., with flexibility coordinated around executive needs. Occasional evening or weekend work may be required for partner, collaborator, or community events. This is a hybrid role. Candidates must be based in the Baltimore Metropolitan area and able to work in-person as needed at Baltimore area offices, co-working spaces, and/or client / collaborator sites.
Travel
Local travel is regularly required; candidates must have a valid driver’s license and consistent access to a vehicle. Occasional regional travel may be necessary for company or client needs, and limited domestic travel may be required for meetings or conferences.
Qualifications
- Relevant experience (2–5 years): Supporting senior leaders as an Executive Assistant, Administrative Assistant, or in a similar support role. Equivalent professional, community-based, or lived experience will be considered.
- Executive support fundamentals: Strong calendar management, inbox triage, meeting coordination, and consistent follow-through across multiple leaders and priorities.
- Organization & systems thinking: Ability to create, maintain, and improve simple systems and workflows that help work run smoothly in growing organizations.
- Judgment & discretion: High attention to detail and the ability to handle sensitive information with care, sound judgment, and confidentiality.
- Clear communication: Strong written and verbal communication skills, with the ability to communicate effectively across teams, partners, and stakeholders.
- Admin / Ops Tool: Comfort using and learning digital tools such as Google Workspace, Slack, scheduling platforms (Calendly, Doodle), CRM’s or lead trackers, project management tools (e.g., ClickUp, Monday, Jira), financial tools (e.g., QuickBooks, Bill), and data tools (e.g., Airtable, Tableau).
- Mission-driven comfort: Familiarity with community-based, nonprofit, or social impact environments and comfort working in fast-moving, growth-stage settings.
- Education (preferred, not required): Bachelor’s degree or equivalent professional, community-based or lived experience.
Timeline of the Selection Process
- Application Open - January 20 – January 30, 2026
- Zoom Screens - January 26 – February 6, 2026
- Short Skills Check - February 16 – February 18, 2026
- Final In-Person Interviews - February 19 – February 24, 2026
- Expected Offer to Final Candidate - February 27, 2026
- Expected Start Date - Week of March 2, 2026
Accessibility Accommodations
If you need accessibility accommodations for any portions of the selection process, please let us know so that we can arrange these in advance.
Apply
If you are interested in applying for the Executive Assistant position, please submit your application here, including (in .pdf format) a resume and customized cover letter–it doesn’t have to be long, but should indicate why you are applying for this role.
Please note that this job description is not intended to be a comprehensive listing of all activities, duties, or responsibilities required of the employee in this role. Duties, responsibilities, and activities may change at any time with or without notice.
Endeavor TBD LLC is an equal opportunity employer that does not discriminate on the basis of race, color, religion or belief, disability, gender, nationality, ethnicity, sex (including pregnancy, childbirth, or related medical conditions), gender identity or expression, sexual orientation, or any other status protected by law