Gregg: How Workiva is Reshaping the Business of Corporate Data

The Charleston Digital Corridor's Leadership Profile Series is focused on the individuals who are driving the Charleston tech scene forward. This series is brought to you with support from Charleston Southern University.

Will Gregg is vice president solutions for Workiva, an enterprise cloud platform for data collaboration, reporting and compliance. Based in Ames, Iowa, the company's original product is Wdesk. Workiva recently opened an office in Charleston, where its newer product, Wdata, is based. Gregg joined Workiva in 2011 and heads the Wdata operation.

In your own words, what does Workiva do?

We build software for teams that helps them work together better, particularly as it relates to complex, collaborative reports. If you need to whip up a word document or jot down some notes, you wouldn't use Wdesk. But if you are a financial professional or an accountant at a public company and you have to produce a 10-K or a 10-Q or an 8-K or a proxy statement, or if you are producing a managerial report or an executive report or a board report -- those are all things that involve lots of people, lots of complex data consolidation, data-collection processes. They need to be tightly controlled and they need to be auditable. That's fundamentally what our software provides: A really cool, browser-based, collaborative reporting environment that helps teams work in a more controlled and automated way.

Where did you grow up? What was life like?

Columbia, S.C. My dad is a veterinarian in Columbia. My parents are both Charleston natives. My dad went to vet school at Georgia, and then he started his practice in Columbia, and we just kind of ended up there. For many years, my parents had intended to move back to Charleston. But I think by the time they were ready to move, we had roots and were in school and all that. Most of our family is here, so we were kind of the odd ones out.

My mom was stay-at-home with three boys, and it was chaos everywhere all the time. I was probably the chief chaos creator. I'm really close with my brothers still. We were probably like any other kids in Columbia, S.C. Fairly middle class, straightforward upbringing, running around in the woods. My dad's a huge outdoorsman, and we got an element of that.

My favorite parts of my childhood actually were being in Charleston. My grandparents have a house out on Folly Beach, and they used to spend summers out there. We would go spend a week at Folly, and I'd go fishing with my grandfather, play in the surf, all that kind of stuff.

What was your first job, or most memorable early job? What did you learn from it?

I was entrepreneurial from the outset. In high school, I was kind of a fixer. I used to do all sorts of little odd jobs for people. I had a little handyman business, and I would put in bathtubs for people, I would repair lawn mowers, anything mechanical that needed fixing. That was my first little attempt at building a business. My dad and grandfather were crazy handy. I learned a lot from them.

One of the most enriching experiences I ever had was selling Cutco Knives, actually. That was my first time really selling anything. As a 17- or 18-year-old kid, going and sitting down with adults and presenting them with options and communicating the merit of a product and all that stuff was fascinating. I learned a ton doing that. I learned a ton about selling. I learned a ton about people. I learned a ton about business. And also, it's an amazing brand they've built. The products are phenomenal. That's one of the other things I learned: Sell things you believe in.

What drew you to Workiva?

The people are what drew me to the company. I was at another software company before Workiva, and we were reselling software to mechanical engineers. The distribution model that the organization and its resellers used got to a point where it didn't work very well anymore, and I was ready to do something else. I didn't want to go work for Salesforce or some big company because I wanted to learn how to build startups. I thought, "I need something that's like, 20 to 50 people, that has room to scale, that's got experienced leadership."

I was talking to a buddy of mine who I had worked with for years, and he had stumbled upon this LinkedIn job posting for this little company in Iowa. I think Workiva being in Iowa was interesting, because not a lot of people gave them much consideration early because of that. You didn't build technology companies in Iowa. When I first started talking to them, I struggled with the idea of working for a technology company in Iowa. I thought, "What kind of self-respecting technology company would base themselves there?" But what I found out was really interesting. The people -- they're Midwestern people, they're super nice. They are family oriented. They have high integrity. And so, the culture we have as an organization in some ways is a manifestation of where we started.

It took some convincing to get me to go out to Iowa for an interview, but I did. We were in Ames, which is close to Iowa State University. You fly into Des Moines, and then you have to drive like 40 minutes, and it's cornfields. I pulled up to this little nondescript building, and I thought, "What am I doing?" But then, I walked in the front door, and in the first 30 seconds, it was like walking into a fog -- you could feel the culture. It was palpable. It was like walking from inside to outside on a hot summer day in Charleston. That culture was so infectious, and the people were so excited and energized by what they were doing.

The office wasn't fancy. It was pretty humble. People were stacked on top of one another. There was just this shared enthusiasm about what they were doing. It was impossible to ignore. That was what I had been looking for. It was just such a perfect cultural alignment.

I met the founders, who had already built another company, taken it public and sold it, taken some time off, and this was their second go-round. Those round-two founders generally have really, really high odds of success, and they had a phenomenal idea.

So it was that. Meeting all the people, feeling the culture. There was just such an alignment in terms of their values and my values. I called my wife when I walked out of the building, and I said, "You're not going to believe this, but this is the place."

Did you move to Iowa?

No, I never did. I started as a seller, and because I was a seller, I was remote. ****

How did you come to be in Charleston?

My wife and I had been in Charlotte for about eight years prior to coming back to Charleston in February 2015. We were driving back and forth all the time because we had so many friends here, and there was always a family event, like a birthday or a wedding or something. We came to the realization a couple years ago: Why do we live in Charlotte? Our life is in Charleston. All of our friends are there. Let's just move to Charleston.

What obstacles have you faced building your business? How have you overcome them?

One of the biggest challenges we had was breaking into a very well-established business. If you are a public company, historically, you call RR Donnelley. You send them notes and they send you back notes, and they edit your notes, and it's this tedious back-and-forth trading of physical papers and emails and commentary and notes. And then, at the end of the day, they do this magical thing and they file your document with the Securities and Exchange Commission. That business existed unchanged for an incredibly long period of time.

One of our original founders was a CFO and understood there's got to be a better way of doing this with technology. Cloud was really early, it wasn't a big thing yet. We were going to companies who'd never used software to do this thing before; they used people to do it. They'd had valuable relationships with these people for very long times. A lot of times they had the types of perks that you would associate with that: football tickets and box seats and those kinds of things. Those are hard relationships to break. They trusted those people. They had high-level executive relationships. And now here we are, and we're saying, "We're a new company who you've never heard of. We're in Ames, Iowa. But we're a technology company, we promise. We're going to try to sell you a cloud solution for your pre-release public financials." Which is probably the riskiest thing you could ever ask a company to do at a time when the cloud wasn't that mature and nobody in the enterprise world had accepted it as being safe. Those were monumental challenges.

To overcome them, you basically have to change the view of the market. It was expensive and very, very hard for us to do because we were early. Being early was exceedingly valuable for us, but it was also exceedingly painful and required a lot of patience. We were going to these really complicated, sophisticated organizations with a brand-new product that they perceived as being really risky to solve a problem that they felt like was already solved. You had to change the way people thought about things. We had to convince them that the cloud was safe. We had to convince them that our way was a better way.

We had this slide, I loved this slide, it was one our marketing team put together. It was a picture in Workiva green, and it was these Little Leaguers sitting on a bench with numbers on all the backs of their jerseys. And, remember, we're selling to accountants and finance people who spend their lives with numbers. The slide said, "Spend more time with the numbers that count." Meaning the kids.

I wasn't in this meeting, but as the story goes, we were meeting with a huge New York bank, probably one of the top five banking institutions in the world, and here we are at this point still a fairly young company, not a ton of customers. One of the execs walks into the room five minutes late, presentation had already started, and she points at the slide, and she's like, "That's my son." Not physically, but metaphorically. "I've missed every single game this season. If you can figure out a way to get me to his baseball game, I'll buy whatever it is you're selling."

So we were onto something. And then once you get that cultural change -- because with all great products, you're changing behavior in some way -- it can just cascade. Once we got through those first 200, 300, 400 customers, we'd earned some creditability and we had a bunch of referenceability and our customers were just fanatical and we had no churn and they loved it, they would call other people for us. It was just amazing. It just took off. But getting that first handful is just the hardest thing in the world.

It's hard even now. We're doing it all over again with Wdata. It's the same thing.

Your team in Charleston is focused on Wdata. What is the market for Wdata, versus Workiva's original product, Wdesk?

We've always sold to a silo that would be accounting or a finance team or an external reporting team. The fundamentals of the problem we're solving for external reporting folks apply to a much wider range within a company group. We just were targeting it at a very isolated group. So part of the goal with Wdata has been to kind of walk that up within the organization to people who have a more global view of how all that data fits together.

What's the hardest or most important lesson you've learned in business?

Sometimes you have to make really challenging decisions for the benefit of the whole that are incredibly painful for a couple people. That's inescapable when you run a business. If you don't have the courage to make those really difficult decisions that affect the masses, then you can quickly lose the masses for one person. That's really difficult to reconcile, especially as a person who's generally pretty empathetic.

What advice would you give aspiring entrepreneurs?

The hardest thing to learn as an entrepreneur is when to trust yourself and when to trust others. There are times when you need to do both. Sometimes it's not easy to figure out which way is right.

Sometimes you have a ton of self-confidence and you go, "I know everybody else is telling me this is wrong, but I know this is right." I've been in a lot of scenarios like that. And then there are also scenarios where you are really confident in a certain direction and others around you maybe are not. Sometimes it's good to listen. Sometimes you can convince yourself of the wrong thing. Being objective and being thoughtful and trying to really consider other opinions is really important. I think it's developing that instinct for when to trust yourself and ignore the noise, and when to seek out and embrace advice from people who have been there and done that. That probably is the most critical skill.

The other thing I've learned is that building a company successfully is so much more about people than anything else. These businesses are comprised of humans, and especially in software, they're your IP, they're your product, they're your everything. It's so much more important to get a really high-functioning, high-quality team together than it is to land on the perfect idea. A high-quality, high-functioning team can always iterate their way to a successful idea. But a dysfunctional team, even with the best idea, is not going to be successful.

What advice would you give new graduates seeking to work in the tech industry?

Define what you want and seek out a place that can give that to you. If you want to learn how to build businesses, you need to be somewhere small that's growing. If you want to work for a huge-name company like Google, then you want that big-box experience as soon as you can get it.

What's the biggest misconception about being an entrepreneur?

There are all sorts of different kinds of entrepreneurs. What we do is a very specific type of entrepreneurship. We do B2B SaaS software. Probably the biggest misconception I think people have about entrepreneurs in that space is their age and the odds of success. The odds of success are exceedingly low and the age is much higher for people that tend to build sustainable, long-term valued companies than what you hear about.

The perception is you have to be youthful to be an entrepreneur, to build strong, creative businesses. In B2B, that's wrong. And it's because when you're selling to other businesses, you have to have a certain level of domain expertise that you acquire over time, and I don't think there's a shortcut to that.

What has it been like building your technical team in Charleston?

Building the technical team has been about trying to seed it with the right people and just be really, really careful on those initial hires. Because that's our culture. That core group of people in Charleston is a small group, and you just can't make a mistake. At our scale, everybody has to be right. They have to work together well inside and outside the office. They have to respect one another. They have to be high quality and they have to be able to attract high quality, because a lot of what we do is recruiting.

It's been a little harder to hire people here than I was hoping, candidly. I think the market is still a little smaller than I would like, but it's growing. Inevitably, we will find somebody, it just takes a little longer to find all the right people.

Do you experience any challenges recruiting talent from elsewhere to Charleston?

There are mechanical challenges with people moving and the timelines and that stuff. It's much harder to hire people remotely, especially when you need them quickly. But in terms of attracting them to Charleston, I have not found that it's as difficult for the right person.

We are looking for people who are professionally motivated but probably have some family orientation, too. Maybe it's really important to them that they can walk their kids to school, or they go ride bikes on the weekends. Charleston uniquely provides a lifestyle that I don't think other areas do.

Interestingly, we have gotten a lot of resumes from people who are attracted to that. They're either like me, they grew up on the East Coast, they grew up in South Carolina and they want to come back and now they feel like there's an opportunity to do that. Or they've lived in San Francisco, downtown with two kids, barely making ends meet and they're probably making $250,000 a year because it's so outrageously expensive to live there, and they're just going, "I don't want to be part of this rat race anymore. Get me somewhere that has a reasonably affordable cost of living, that has opportunity to enjoy my family and be outside."

Are you a Mac or a PC? iPhone or Android?

Mac, iPhone.

What is your usual Starbucks order?

Venti Pike, cream and sugar.

Outside of work what keeps you busy?

Fishing, kite surfing, family.