Jason, Matthew, and Katherine on how Dropbox and HelloSign make each other (and their teams) better

4 min readFeb 7, 2020


At Dropbox, we’re always invested in growing. But we want to make sure we’re doing so in ways that make sense and are healthy for not only us, but for the new team members that will be transitioning into our company. As we celebrate the anniversary of welcoming HelloSign to the Dropbox family, Katherine Kassing, Jason Devoir, and Matthew Lingner reflect on their experiences during and after the acquisition.

Katherine, an Administrative Business Partner with a background in communications, has a unique perspective — she joined HelloSign about six months after the acquisition. For her, one of the greatest perks of joining Dropbox is the potential to bring more visibility to HelloSign — a product she feels can help the world work better.

“HelloSign is really looking to make these inflection points in your life easier; you’re signing contracts because you’re getting married or buying a house or going through other really big moments in your life. We’re trying to make them easier no matter where you are and really revolutionizing what it means to create those transactions, which really fits in with the vision of Dropbox, creating a smarter way of doing things. One of the first things I thought when I heard about HelloSign was wow, I wish I had known about this before. This would have been really helpful in my life! So that’s what the acquisition is about, scaling HelloSign. People know what Dropbox is, but it will be really great when people know what HelloSign is. We can help people make things easier and focus on what matters.”

Jason, a Senior Technical Recruiter, is also passionate about the benefits that HelloSign can provide to the world. He started working for HelloSign about three months after the merge with Dropbox. As a former teacher, he immediately realized that his team was still dealing with a significant learning curve — but also that they weren’t alone in figuring it out.

“I think change is probably one of the hardest things for people to deal with in life in general. So when it comes to your job, it can really be tough. At first, it was a bit rocky. But the people we did gain from Dropbox are just fantastic and have been so great in helping us weave our way through the process. I can’t give them enough applause and thanks for making that transition much easier. The Dropbox recruiting team has been very supportive.”

Matthew, an Engineering Manager, started his interview process when HelloSign was still an independent company. Coming from a company filled with passionate, caring people who worked with nonprofits, he was looking for a similarly positive environment, which he found at HelloSign. He accepted his job offer the same day that it was announced that Dropbox was acquiring HelloSign, and was excited to see how both company cultures would come together to make each other even stronger.

“I think that there’s always somewhat of a playbook with acquisitions and a question of how much of that culture you’re going to maintain if you have a company that cares about each other. Is everyone going to leave? Is it going to be a situation where a lot of culture is gone and it becomes a bureaucratic big company thing? But I haven’t seen those concerns play out at all. In terms of team culture, we’re part of formulating the new Dropbox values, and we’ve had access to the DEI team to make sure we form a more diverse and inclusive culture especially within engineering. There have been a lot of positive things that have played out because of the acquisition. We’re actively thinking about how we keep HelloSign’s culture unique.”

As Matthew pointed out, with any acquisition, there is the possibility for challenges when integrating two cultures into one. Luckily, people who embody our values on both sides of Dropbox and HelloSign came together to become a unified, strengthened team, one that Jason also found was excited about the potential for growth and learning.

“We went to an offsite in Austin a few months ago, and everyone was excited to meet us. Before then, we weren’t really sure about each other; it was almost like a middle school dance with all the boys on one wall and all the girls on the other one and it’s like, should I go ask her? We weren’t really sure what to do. So I was really excited about the offsite because all of us were together. As soon as I walked in and felt the energy there, I knew that it was going to be a good experience for me. I knew I was also going to grow in my career, because you’re never too old to learn and grow and become better at your trade. We should always be willing to adapt and learn and become better at what we do, and this atmosphere has allowed me to do that. We can take advantage of so much training, and every year we get funds to help with that, because they just want us to get better.”

Want to learn more about how the teams at Dropbox and HelloSign function, and how you might become part of the journey? Check out our jobs page.




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