Even on a summer family vacation, President Barack Obama is followed by an entourage whose behind-the-scenes movements are juggled by a woman who was born into politics and has been with him since his Chicago days.

Ashley Tate-Gilmore heads the White House Travel Office, a five-person operation that handles precise logistics behind every presidential trip. The details usually go unnoticed by the public, unless something goes horribly wrong.

Tate-Gilmore not only acts as a high-stakes travel agent for White House press and staff, but a mini-ambassador who is often the first to arrive at presidential destinations. She’s used to being underestimated, a 29-year-old woman who is quick to laugh and signs off every email with a smiley face.

She said it was clear from her first meeting with foreign officials when she took over the job three years ago that they weren’t expecting to take directions from a woman who looks so young.