“Every now and then, somebody might confuse me for a hipster,” Mr. Hale said of his time in the new Clinton orbit, “until they hear me talk.”

For almost all of his life, Mr. Hale has been talking about the Clintons. His mother was a county chairwoman during Bill Clinton’s 1980 run for governor here, fielding a call from Mr. Clinton after midnight on the evening of his defeat as he agonized over what went wrong. Mr. Hale had been dispatched, in vain, as a 5-year-old to hand out stickers to seniors for the cause.

In 1996, he left college to work on the Clinton-Gore re-election campaign, gravitating toward the advance team, the group responsible for the planning and execution of events and trips.

Mr. Hale first accompanied Mrs. Clinton during a trip to Portland, Me., wearing a suit and standing watch all night in the hotel lobby because a practical joker had insisted that protocol required it.

Two decades later, after stints on Mr. Clinton’s post-presidency team in New York, John Kerry’s 2004 campaign and Mrs. Clinton’s primary run in 2008, Mr. Hale has cobbled together his own set of rules.

He knows which cities have superior “balloon capabilities” and how a plaque’s reflection can upend lighting plans. He knows where to position carpets to improve sound quality and how many chairs to place onstage depending on the tone of Mrs. Clinton’s planned remarks. (For more formal gatherings, he often keeps voters out of the main camera shot.)