Software for the government is awful. I previously wrote about the terrible navigation software for Navy submarines. Commenters at Hacker News chimed in with their experiences with defense software. It's really bad!

It's hard to replace bad software in the Defense Department. Labyrinthine procurement regulations lead to long sales cycles. Long sales cycles starves new companies of cash so they either fold or choose not to enter the market. Status quo prevails.

This same tension exists in commercial enterprise sales. As a result, many  software startups now initially forego the top-down enterprise sales channels and drive bottoms-up adoption from end users. This go-to market category of "bottoms-up" sales seems super promising for folks trying to overcome blockers in government procurement and solve problems with defense software.

Selling into DoD today

I asked a close friend and someone familiar with defense contracting, "What's the path from 0 -> 1 on fixing something like VMS?'

His recommended path was something like:

  • Get a time & materials contract to diagnose the problem with VMS.
  • Parlay the above into a program manager slot on a contract.
  • Open a veteran owned LLC and further subcontract with the big defense contractors. This allows the big contracts to get a "small business" credit while I could set my own $ rate.

The play would be to become a subcontractor for the big guys of the defense world. On the face of it, that's not particularly ambitious or interesting. On the other hand, it is almost certainly good money, if I could get it.

I'd characterize the above sales motion as top-down or enterprise-led. One has to find the people who are charged with the solving the problem and the people who control the budget and then convince these different groups you're the solution. By the way, these people are probably totally distinct from the people who will actually use your product once purchased!

Slack, the workplace chat software, can give us another model of how to build and sell into the DoD.

Note: If you know a bit about government/DoD procurement processes, I'd love to hear from you!

An example of bottom's up software

The workplace chat service Slack is often the defining example of "bottoms up software." Slack had its origins as an internal tool for a video game company, which decided to sell workplace chat software after the game didn't work out.

Rather than selling to heads of HR or CTOs, Slack "sold" itself directly to the users.

Slack would get a few employees at a company to organically adopt the product. "Cool, I've been looking for a way to better communicate with my team," one employee might think as they downloaded the software for free. Then, Slack usage would spread until it reaches a threshold that it just "makes sense" for the business to sign an enterprise contract with Slack.

By making a product that's fun and useful, Slack got buy-in from end users who then internally sold the product and drove its adoption. Where might a company succeed with this for the Defense Department customers?

What would it look like in the Defense Department?

Here are three product categories that seem perfect for bottoms-up adoption by members of the DoD:

  1. Training
  2. Professional Development
  3. Quality of Life


A lot of a servicemember's time is spent in training. I spent three years on a submarine. Prior to that I spent the previous 18 months in a training pipeline. Once on the boat, we trained everyday.

Training is very serious. I literally saw a guy get leg swept by his instructor on the conn of our submarine because he couldn't perform a trigonometric function fast enough! If you offered to improve his learning speed or memory recall, I'm sure he would have been willling to pay for it.

While training is important, the current studying and teaching practices are not very "scientific." A lot of it could be Anki-fied.

Probably the largest market to serve would be training for aviators. At two years of training, it's one of the longest pipelines. Plus, there are a lot of training products out there for civilian aviator students from which to draw inspiration.

Professional Development

"How do I promote and advance in my career?" is a fantastic problem for a bottoms up approach. Servicemembers have an incentive to care about promotion: they get paid more!

Today, most enlisted servicemembers take an annual test related to their job specialty. If they place within the top X%, they promote. The material they need to know is publicly available and there already exists outside study materials that they purchase to prepare. I haven't reviewed the material myself, but I'm bet someone could do a better job.

Quality of Life

While a vague category, I do think there's strong potential for software that improves the quality of life of a servicemember.

There's a lot of manual spreadsheet work that could be automated. A lot of HR processes are poorly documented or explained. There are annual requirements that are easy to miss. The healthcare system is a mess and confusing to navigate.

There's a whole site, Kelly Beamsley, that just serves as a directory of all the DoD websites a servicemember has to access because it's so confusing. What does the next version of something like this look like?

I bet people would pay a few dollars per month if you made their lives easier along some of these dimensions.

Bottoms-up is just the beginning

Solving any one of these problems by themselves seems unlikely to unlock a huge business opportunity. Taken alone, none of them will win the next war.

I think the value of trying a bottoms-up approach to solving DoD problems is the potential to breach the fog of procurement processes. If you have an established business selling to servicemembers, it seems like it might become easier to sell into  the enterprise.

Perhaps one could view Slack as a cautionary tale for such an approach. Microsoft copied the product and rolled out Teams through their enterprise sales channels. Public markets doubted Slack's ability to beat Microsoft at the enterprise game, leading to Salesforce's acquisition of Slack.

I think that's too pessimistic of a way to end. The acquisition was for $28B! Slack built a large business, giving rise to a whole generation of products geared towards a bottoms-up go-to-market strategy.

I'd love to see someone take such an approach to servicing the Defense Department, or government, more broadly. Might have to do it myself!

Interested in working on bottoms-up software for the DoD? I'm looking to build a community of folks working on such problems. Drop me note and collaborate with likeminded problem-solvers.