Paul Gillespie

Paul Gillespie a long-time advertising sales executive in Boston, is our O.G. Lead Dad of the Week.

Paul was a Lead Dad before the term existed – and certainly, before any company thought working from home was anything more than a synonym for slacking off. From the late 1990s on, he persisted, so that he could be present for his three kids – two of whom are twins – and his wife, a teacher.

How did he quiet his managers, stay productive, and still be a Lead Dad back then? “Performance,” he said, from his basement office overlooking what was once his kids’ playset. “I shut them up with sales. That’s the nice thing about being in sales – it’s pretty easy to define success. There are objective measurements of success.”

Yet at times, he felt under extra scrutiny. At one point in the early 2000s, he was working for an MIT publication called Technology Review and his boss was deeply skeptical of his ability to work remotely. Gillespie kept selling and it wasn’t an issue. But the work environment wasn’t ideal.

“My MIT boss was a more traditional guy, and he hated me working from home,” Gillespie said. “There was always this tension. One of the things I saw from bosses like him was suspicion. It’s such a ridiculous concern, but it’s still there today.”

Today he works for RR Donnelley which doesn’t even have an office for him, he said. How’s being remote worked out for him? “I was salesman of the year in 2022,” he said. Moreover, he’s got a great relationship with his wife and adult children.

Thanks, Paul Gillespie, for sharing your wisdom and welcome to The Company of Dads.