Flex Flagger Jobs in Washington (NOW HIRING)

Executive Assistant

American AI Logistics is looking for a highly organized, personable Executive Assistant to support our founders. This is a role we're hiring primarily for temperament and personality fit — more than for a specific resume line. We need someone warm, easygoing, and genuinely good with people: the kind of person who can walk into a room, put everyone at ease, and build real rapport with clients and staff, all while running a tight, dependable operation behind the scenes. The two founders work and operate very differently, so this person needs to comfortably flex between both styles — reading what each one needs day to day and adjusting accordingly, rather than applying a single approach to both.

• Manage complex, shifting calendars for the founders, keeping everyone's time protected and conflicts resolved before they happen.
• Book flights and hotels for business travel, handling changes and last-minute adjustments smoothly.
• Communicate directly with clients and vendors to secure and confirm office space.
• Schedule and confirm board meetings well in advance, with reminders and calendar confirmations built in.
• Act as a trusted gatekeeper and point of contact, taking administrative and logistical work off the founders' plates so they can focus on the business.
• Anticipate needs and follow through independently — this role requires someone who runs with things rather than waiting to be asked.
• Manage and triage founders' email inboxes, flagging priorities and drafting routine correspondence.
• Prepare agendas, briefing materials, and follow-up notes for internal and client-facing meetings.
• Process expense reports and reconcile receipts for business travel and purchases.
• Help plan and coordinate company events, off-sites, and client meetings.
• Handle sensitive and confidential information with sound judgment and discretion.

This role reports to Tim day-to-day and supports both founders, who work in very different ways — you'll need to flex between the two:

• John focuses on federal sales and casting long-term vision — he's energizing, inspires people to get on board, and moves fast. He needs someone who can handle the details and logistics independently.
• Tim is more analytical and detail-oriented. He wants board meetings booked well ahead of time and calendars double-checked and confirmed.

Above all, we're looking for someone with a magnetic, likable personality and genuine people skills — someone easy to be around, discreet, unflappable under pressure, and naturally warm with clients, vendors, and the team. Just as important is a strong anticipatory instinct: this person sees a need coming before it's spelled out, and is already handling it. The ideal hire is the one who can say "that's already done" when the founders are about to ask for it — not someone who waits for a task list.

• U.S. citizenship required.
• Reliable, consistent on-site attendance — including during government shutdowns, continuing resolutions, or other disruptions common to the federal contracting space.
• Government contracting (GovCon) experience strongly preferred; relevant military experience is also highly valued.
• Proven track record as an executive assistant, personal assistant, or similar role.
• Excellent written and verbal communication skills.
• Able to work on-site in the Washington, D.C. area.

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