How Military Veteran closes partnership deals faster and saves 100+ hours a year

The Military Veteran founders have helped thousands of veterans transition into higher education and meaningful careers. Since implementing DocSend and Dropbox Sign, they better understand how their prospects behave and close deals faster.

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How Military Veteran uses Dropbox Sign

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100+ hours a year saved to focus on 
their primary mission

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25% jump in revenue and exceptional ROI

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30% reduction in time to hire

Company Profile

Founded in 2022
Headquartered in San Francisco, CA
Company Size: 7

A deeper dive with Military Veteran

The Challenge

Helping more veterans by streamlining sales and HR

As a former Marine who understands the emotional battle of switching from military to civilian life, Brendan Aronson is on a mission to help other veterans march meaningfully into the next stage of theirs. Brendan’s company, The Military Veteran, builds a community, produces inspiring content, hosts recruitment events, and helps companies hire their next generation of business leaders. Through The Military Veteran and his past non-profit work, Brendan and his cofounder have helped thousands of veterans transition out of the military and into higher education and meaningful careers.

To fund its operations and continue to grow, The Military Veteran sells sponsorship packages for its recruitment events to enterprise customers, medium-sized companies and venture-backed startups. The deals are a win-win. They bring vital revenue for The Military Veteran, while providing excellent publicity and goodwill for their customers’ brands while helping them hire from this fantastic community. The Military Veteran also helps companies hire through direct placement.

Even for a purpose-driven business such as The Military Veteran, organizing and closing sponsorship deals can be challenging. They were determined to net more revenue and help more vets, but laborious manual processes across their sales workflow had the whole team under siege.

The task of sending out and tracking sales decks was a particular pain point. It took significant time and resources to pull together all the relevant collateral and attachments into an email. If they noticed an error after they’d hit send, they’d need to circle back, update the document, and resend it. Any errors or additional friction for the prospect left The Military Veteran at risk of losing the sale.

Even more problematic, The Military Veteran had no visibility into when prospects opened the deck, what they looked at when they did, or whether they were genuinely interested. Without that insight, they relied on their best guesswork to decide when to follow up. At best, this extended the sales cycle. At worst, it risked missing out on a deal altogether.

The team faced another avalanche of admin when prospects were ready to sign a deal. The Military Veteran relied on the age-old method of printing, signing, and scanning pdfs, which caused unnecessary workload and friction at the very point it needed to be easy.

Paper-based processes were causing more issues on their HR frontline. The company is composed of veterans and military spouses and onboarding them required everything from NDAs to IP Assignment Agreements to be signed. As things stood, it took Brendan 90 minutes to locate and collate all the documents, and that was even before he collected signatures.

As a time-strapped CEO, Brendan was determined to remove the heavy lifting from sales and HR. The more the business could streamline and automate its processes, the more deals they could close and the more veterans they could ultimately help. It was time for a digital about-turn.

“Adopting DocSend and Dropbox Sign was a giant step forward for our business. They’ve reduced the barriers in our closing process and become a critical part of our sales funnel. Without them, it would be like stepping back into the dark ages.”

Brendan Aronson, Co-founder and Chief Executive Officer
The Military Veteran
The Solution

Secure and streamlined way to close deals and onboard faster

The Military Veteran adopted DocSend and Dropbox Sign to remove manual legwork from their sales and HR workflows, gain more intelligence into how their prospects behave, and ultimately get more deals signed faster.

With DocSend, The Military Veteran has a central platform for sharing and tracking the performance of their sales decks. Instead of wasting time hunting down siloed files and adding clunky attachments, The Military Veteran pulls the relevant documents into DocSend then creates a secure link in one click. Prospects have nothing to download and the DocSend link can be viewed, troublefree, on any platform.

While The Military Veteran was previously in the dark about what leads were doing with the materials they sent, DocSend puts real-time intelligence at their fingertips. They’re notified when a prospect looks at the deck, and receive analysis on the specific slides they’re evaluating, and how long they’re spending there. Document tracking provides a huge competitive advantage says Brendan:

“It’s perfect because you know you're top of mind for the client, so you can strike while the iron’s hot, follow up with them right then, and see if they have any questions and drive the deal forward.”

The analytics are so granular and actionable, The Military Veteran uses them to fine-tune their sales collateral and reorient on the pages that are performing best.

Yet another weight is lifted, because DocSend makes it easy to fix typos and send updated versions of sales materials after you’ve hit send. Brendan simply updates the document in DocSend and every link he’s shared is automatically updated. So any potential confusion or embarrassment with a prospective client is instantly avoided.

When leads are ready to sign an agreement, The Military Veteran uses eSignature with Dropbox Sign to get deals closed faster. Dropbox Sign’s easy, automated workflow, means Brendan selects the agreement he needs signing, adds the signer’s contact details, and sends it for signature. On the prospect’s end, they can sign from any device without logging in, so they typically do it there and then.

In the past, chasing up signatures was always at the back of Brendan’s mind distracting him from other important tasks. With Dropbox Sign, he receives notifications of the contract’s status automatically. He says: “The whole process is owned in one place and every time I log in, the system reminds me if I'm missing a signature on something. I don’t even have to follow it up myself, because Dropbox Sign reminds prospects automatically, which is huge.”

The Military Veteran also takes advantage of Dropbox Sign to onboard interns faster than ever. Instead of laboriously locating NDAs and other agreements every time he brings on a new intern, Brendan creates reusable templates in Dropbox Sign and sends them in seconds. Onboarding used to be a battlefield. Now it’s achieved with total ease. Brendan says: “I onboarded someone the other day and it took me probably 30 seconds because I already have the forms saved there. It's one click, they sign it and you're good to go. It's awesome.”

The Results

DocSend and Dropbox Sign save 100+ hours a year

The Military Veteran saw immediate results from adopting DocSend and Dropbox Sign. They save time and cost, close more sales, and have more time to pursue their primary mission—transitioning veterans out of the military. Brendan says: “We saw great results within the first week. It was just like an obvious, giant step forward. They’re just great tools.”

Less time on admin, more time for veterans
With DocSend and Dropbox Sign eliminating so much manual work, The Military Veteran saves at least two hours a week—or 100+ hours a year—to focus on selling, hiring, and nurturing customer relationships. Brendan says: “I can spend more time doing the stuff that I love as opposed to the administrative portions of the job. I spend more time meeting with clients, trying to win new business, and most importantly working for the community that we serve.”

Remarkable ROI and 25% rise in revenue

The financial benefit of implementing DocSend and Dropbox Sign dwarfs the investment The Military Veteran has made. Because they message prospects the moment they’re looking at their sales materials, they close more deals and faster. Brendan says: “Dropbox Sign speeds up the closing process and reduces the barriers to someone closing. I’d estimate it has played a direct role in lifting our revenue by 25%, so it’s a critical part of our funnel.”

Brendan adds that the software’s ROI is remarkable: “Even if we only closed one additional sale by using the software, it’s a dramatic ROI—well over 100%.”

Hiring faster and helping more veterans

Since adopting Dropbox Sign, The Military Veteran keeps the hiring process short and sweet. Collating and sending onboarding documents has been cut from 90 minutes to just 30 seconds. Time to hire, meanwhile, is reduced by 30%, which saves hassle and time, gets veterans into work faster, and supports their reputation as a supportive and efficient workplace.

Making their mission count

Dropbox Sign and DocSend work together seamlessly to solve multiple problems for The Military Veteran. Brendan says: “We get to spend more of our time now doing things that we either really enjoy or that create value for our customers and veterans, which is how I want to spend my time. I'm a big fan of Dropbox Sign and DocSend. They enable me to help more veterans find their next roles in their civilian career, so I appreciate that.”

The Future

What’s next for The Military Veteran?

Looking ahead, Brendan believes the positive impact of Dropbox Sign and DocSend on The Military Veteran’s operational efficiency and financial success will keep on growing. He says: “The beautiful thing about working with these products is that they'll scale with us. As we continue to grow and scale our team and our impact, they'll become an even more critical part of our workflow.”

Brendan adds: “We are at a critical inflection point in our business where we’re experiencing extreme growth. The hours saved with Dropbox products will be magnified in the coming months across our growing organization.” If your company is looking to hire veterans, reach out to us at

Ready to see results like The Military Veteran?
Dropbox Sign makes it easy to get agreements signed online with legally binding signatures and robust security features, so that small businesses can spend less time on admin tasks and more time on growing their business. Contact our sales team today.

DocSend is trusted by over 34,000 companies across the world for secure document sharing and real-time analytics. Sign up for your free trial today.

The Military Veteran uses Dropbox Sign and DocSend to streamline sales and hires
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