Welcome Whitney Bouck, HelloSign's New Chief Operating Officer!

Whitney Bouck HelloSign's New Chief Operating Officer

We’re ecstatic about our newest HelloSign team member and Chief Operating Officer, Whitney Bouck. Not only is Whitney’s list of extraordinary achievements long and impressive, she’s also a foodie, something most of us HelloSign-ers take pride in. Let’s just say, it was a natural fit. 

Whitney joins us from Box, where she ran global marketing, overseeing product marketing, CIO relations, customer acquisition, analyst relations and communication programs. She’s well-known for building Box’s Enterprise business from the ground up. She’s helped build companies from a size similar to where we are now to IPO, twice. 

In partnership with HelloSign’s CEO Joseph Walla and CTO Neal O’Mara, she aims to grow and scale HelloSign to meet the extreme growth in demand from companies large and small. Whitney will also directly lead our go-to-market efforts, including sales, marketing, business development, and customer operations. 

Instead of doing a traditional introduction post, we thought it might be more fun if we shared some questions directly from our crew for a more personal introduction to our newest teammate. 


Was there a defining moment in your career that fueled your success?

When I first discovered the joy in turning light bulbs on for people — getting someone to see a possibility they didn’t believe in before — that was the moment I realized the power of sales and marketing. It really made me imagine the role I could play in inspiring people to buy and use the products I was helping to create.

What’s the biggest challenge you’ve encountered while scaling a company?

Keeping the message consistent in a growing and increasingly dispersed organization. When a group gets bigger, it’s very easy to have a lack of consistency in the story you want the market and customers to hear. And that lack of consistency can result in market confusion, lack of traction, and a misperception about your company’s offering.

I remember the day I overhead an SDR at Box saying on the phone to a prospect, “We’re like Dropbox, but for the enterprise.” That was such a gross understatement of the value and capabilities of Box! It made me realize we’d gotten too big to be able to touch every sales rep and ensure they had the right message and tools to tell the right story. We needed a more scalable and repeatable model. So we fixed it.

It takes extreme diligence to make sure everyone keeps to the same message, differentiators, value, etc. as a company scales.

What excites you most about joining HelloSign?

So many things! But three really stand out.

First of all the founders. Joseph and Neal are amazing — incredibly smart, with great vision, and clearly really good partners. My first meetings with them made it obvious how great it would be to work with them.

Secondly, the market opportunity. It’s pretty clear this is a huge market — what company doesn’t need to automate the workflow around signing agreements? I’m confident we can sell to just about every company in the world.

And finally, the culture. I promised myself that I wouldn’t join a company unless it felt like home. And HelloSign felt like home the first time I walked into the office.

What do you consider your biggest failure? How did you recover?

Not forcing Documentum to focus on user experience enough. Granted, this was back in the day when capabilities trumped ease of use (and before the mobile era, I might add), but I truly think the lack of commitment to great design was the reason for the relatively low number of users for ECM (Enterprise Content Management) systems in general, Documentum and its competitors of the day.

I’ve definitely learned that if you don’t delight users, your product can’t truly be successful.

Where do you see HelloSign in five years?

I’d love to see us as the de facto choice for companies of all sizes to automate the workflow around anything that requires a legally binding signature. Embedded into every business application. And hopefully doing about $300-350M in revenue. Which could mean the company will be valued around $3B!

What are your thoughts on the importance of company culture?

Culture is the heart of a company! When you have a great company culture, it makes work a great place to be and full of people you want to be around. It galvanizes everyone to be almost like a family, or at least a tight team, shooting for the same outcomes. It means we all have each others’ backs and trust one another. And it forms the basis for long-term relationships.

What’s the best advice you ever received?

Believe in yourself. Take risk. Don’t be afraid to stretch yourself. And remember that with change always comes opportunity, so don’t ever be afraid to embrace change.

If you were trapped on an island and could only eat one cuisine, what would it be?

Mexican! I love the flavors and spice of Mexican cuisine and I swear I could eat it every day at every meal.

What’s your favorite thing to do in your free time?

Cook for my husband and/or friends and family. Cooking is a huge passion of mine, and I like to cook 4-5 times a week. It’s my come-down from work and I find it very relaxing. Not to mention delicious!

If you could have any superpower, what would it be and why?

The ability to clone myself! There are times I would love to be 3 places at once — visiting a customer to do a deal, on stage presenting at a conference, and back at the office doing something important with the team. It’d be nice to be able to do them all! 

Welcome to the team, Whitney!    

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