After serving and working in the Army and then in the private sector — focused on technology and finance — Jonathan Moak saw the potential to help both sides and chase his own dream of working for himself.

“There was a gap in the environment where government employees didn’t really understand what the private sector was doing, and the private sector didn’t really understand what the government employees were doing,” said Moak, senior vice president for sales at Inkit, a document generation platform startup.

He saw that gap as an opportunity to help people understand where capabilities fit, he said during the American Society of Military Comptrollers’ The Business of Defense podcast on Federal News Network.

“There’s no malintent on either side. But sometimes the two organizations, private and public sector, don’t really understand one another,” Moak said. “Sometimes, it can kind of be a mystery what’s going on inside the five walls of the Pentagon.”

It’s the reason he founded his own business, Moak Management Associates — only months before Inkit CEO Michael McCarthy convinced him to join the tech startup to help drive sales within government, but particularly within the Defense Department.

After leaving a federal post at Salesforce, Moak didn’t plan to join another technology company — at least not right away. But he came to view the role at Inkit as an ideal way to help government teams while also working to build a program within a startup.

“The mentality is really sort of like being in an infantry company in the Army,” he said. “Everybody has to jump on board and row in the same direction. It’s not that you just have your job function, and you’re in this box, if you will. To do this, you’re going to have to do a lot of things and wear many, many hats. And so that’s a place that I thrive.”

We asked Moak to share some early lessons learned from his own consultancy as well as at Inkit that might help other tech startups break through and be successful in the federal sector. Here’s are five tips he offered.

Breakthrough Tip 1: Make sure your tech meets the need compliantly

Delivering against a mission need while aligning with mandates might seem obvious, but it’s critical in government contracting, where compliance often becomes a gateway to further work.

With Inkit, “we meet the coming zero trust M-22-09 cybersecurity mandates,” Moak said. “We’re both Impact Level 4– and IL5–compliant. So we’re meeting the Department of Defense compliance standards.”

Plus, he said, the technology can help teams across DoD and on the frontlines be more efficient by pulling data from multiple business systems into forms easily.

“All of that data exists somewhere in other business systems throughout the Department of Defense,” Moak said. “There’s really no reason why it couldn’t be automatically filled, the document generated, signed digitally in our system, and then ushered on to the next phase and distributed to its either terminal location or the next step in the process.”

Breakthrough Tip 2: Show don’t tell your tech’s capabilities

Sure, agencies release requests for information and people research  technology online. But letting people test and see a technology in action often makes a huge difference, Moak advised.

“If you can reach out to folks … and just say, ‘Hey, we’d like to come show you our software,’ or you’re at a show — like the Department of the Air Force Information Technology and Cyberpower Education & Training Event down in Montgomery, Alabama —  and you have people come by your booth, and you can give them a three- to five-minute demo,” that’s ideal, he said.

That way, a company can both show the value of the technology, which has worked for Inkit, and build relationships too, Moak said. “With government employees, what’s the time to value? You don’t have a lot of time to step back and admire problems and think about what a path to success looks like. It’s got to be co-created with that relationship and that trust as a foundation.”

Breakthrough Tip 3: Be willing to adapt on the fly

Startups tend to have people doing multiple jobs, and they often have not established the infrastructure, overhead and policies and procedures common to medium and large businesses.

As Moak put it: Some things that seemed important going in, really aren’t, and some that didn’t seem critical, really are.

For instance, he shared a story about interviewing a woman for a sales position on his budding team at Inkit. She asked about the company’s maternity policy. It wasn’t something the small team of fewer than 30 employees had addressed yet.

She made a suggestion. “I took that recommendation to our CEO as soon as I got off the phone with her. And you know, we implemented a four-month maternity policy because there are pros and cons and a cost benefit to that,” Moak said. “We understand that we can finance this. We can figure out how to do it so that we can attract talent.”

Breakthrough Tip 4: Build on relationships you have, but don’t stop there

After working for Deloitte, serving as a soldier on the tactical edge and in the infantry for the Army National Guard, being the acting comptroller for the Army and leading a federal sales team at Salesforce, Moak said he has found many mentors and created many relationships across the defense industrial complex.

Those connections have been immeasurably helpful throughout his career, he said. But they don’t necessarily help address the biggest risk to a startup, Moak said. And what is that risk? It’s government employee turnover, particularly in DoD.

“You’ll have a champion for two years, and then they get promoted because they’re so good, or they move on to another place, and a lot of those efforts sort of wither on the vine when they depart,” he said. “And so you’ve got to find that champion, and then you have to sort of expand that beyond just their control and move it down to their team. That sort of gets that irreversible momentum if you will.”

Breakthrough Tip 5: Take advantage of SBIR but also develop vendor partnerships

DoD’s small business innovation research programs can help a startup gain entrée into federal work, but SBIR funding doesn’t guarantee future contracts.

“That’s a very tough hurdle to cross,” Moak said. The way to scale a startup is through partnership with other established vendors in the GovCon community, he recommended.

A business with innovative technology should look “for good systems integrators that want to work with you, that are going to help you implement your software,” Moak said. “They’re going to do it the right way and help you put your software on its best foot going forward.”

To listen to the full discussion between Jonathan Moak, senior vice president of sales at Inkit, and Rich Brady, CEO of ASMC, click the podcast play button below:

Discover other The Business of Defense podcasts here.

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