Career Pivot To Win: From Federal Employee to Defense Contractor

When Tom Boylan left the federal government to join a DefenseTech contractor, he had spent more than 25 years working in the Navy, much of it leading data center operations.

It was not an easy transition from the federal government workforce to becoming a contractor. Boylan definitely learned from his experience shifting his career and has no regrets.

How did Boylan make the move seamlessly to the private sector? How did he help grow the company he joined, which had begun as one-woman shop dedicated to training Army organizations implementing the service wide General Fund Enterprise Business System, an SAP-based enterprise resource planning system? What advice does he offer other feds making the leap to the defense industry?

Here are four takeaways Boylan shared, that he believes are critical for federal employees transitioning into the DenfenseTech contracting sector.

1. Be Prepared To Embrace Change

“You have to be prepared to do things maybe differently than you have done them in federal service,” he said, adding that would be the biggest message he’d share with people weighing a move from government to the contracting world. It applies whether someone’s retiring from federal service after 30 years or accepting the private sector job when they’re only in their 30s, he said.

But it’s especially true if you are in a senior role in government.

“When I left federal service, I had an executive officer. I had a dedicated admin. I probably hadn’t done a travel voucher in 10 years or longer,” Boylan recalled. “Now, I do my own expense reports. It won’t hurt you. It’s just part of what you do when you’re working at a good small business.”

2. Understand Expectations For Senior Corporate Managers

While it might seem obvious, it is a lot different to move from a job where the entire focus is mission within the federal government to one that is driven by company vision and revenue.

“You’re now responsible for profit and loss,” possibly for the whole company if it’s a senior management role, Boylan said. “You know, income statements, balance sheets, those kinds of things, negotiating with insurance companies about benefits, negotiating about management of the 401K — all those kinds of things you kind of have to work on.”

3. Educate Yourself About The Type Of Contracts Your Company Works On

It is critically important to understand contract types, which Boylan said he often schools young managers about. For instance, it can matter to the business’s bottom line and how it manages a program for a customer if the deal is a time and materials contract versus a cost-reimbursable contract or a firm, fixed-price contract.

“If you’re working under a T&M, you might be able to make a little more money than a cost-reimbursable contract or a firm,” he noted. “And if you’re working under a firm-fixed price task order, you’ve got all this risk that you have to account for in pricing. Learning those kinds of things is important as you transition because you can win work, or you can end up with work, and still not make money.”

4. Realize How The Company Affects People’s Daily Lives

Working in the government, it can be easy to become distanced from the value of money, Boylan stated.

“I’ve thought about this, and not to be disingenuous at all, but sometimes as a federal employee, we would push money around and we would just think, ‘It’s just a stack of paper’ ” tied to a specific mission need, he said.

But now, Boylan sees it quite differently. Not that the funds weren’t important, even potentially affecting life-and-death decisions in government, but the value of the money was more abstract. “Now, today, I’m dealing with real money that pays real people. And I’m very conscious of the fact,” he said. “If we have 200 people working for our company, multiply that by a conservative number of three people in a household, that’s over 600 people that are depending on us — for food, shelter and income. You have to take that very, very seriously when you are making that transition from federal service to industry.”