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CEO Haley Altman on Startup Success and What’s Ahead for Doxly

December 18, 2019

Welcome to Leading Indiana Ambition – a series of leadership stories fueled by Elevate Ventures highlighting entrepreneurship across the Hoosier state. This month, we profiled Haley Altman of Doxly. Stay tuned next month for more!

CEO Haley Altman on Startup Success and What’s Ahead for Doxly

By Rachel Smith, Communications Specialist

As a former Ice Miller partner, Haley Altman is no stranger to capital raises and acquisitions. Altman, Doxly’s CEO, launched the legal transaction management platform in 2016 leveraging her industry experience and scientific background. Just three years later, Altman experienced a new perspective of business transactions when Doxly was acquired by Litera Microsystems. Altman has built a supportive network and a successful team while staying focused on Doxly’s vision – creating a product that can improve people’s lives. Although Doxly is Altman’s first startup, her desire to solve problems began early in life, giving her a head start on her entrepreneurial journey. The Elevate Marketing team sat down with Haley to learn how she went from lawyer to startup CEO and to discuss all of the lessons she learned in between.

Before Doxly, you were an attorney for more than 10 years. What drove you to become an attorney?

I was a science major – chemistry. I started working in cancer research when I was in high school. But in college, I started taking political science classes and did a lobbying internship in Indiana, and I just loved it. I loved the idea that I could help influence policy that could get more science initiatives to move forward.

I took a year off between college and law school, because I was debating between med school and law school, and I did an internship with Ice Miller – the law firm I ended up working with on behalf of Eli Lilly. I lobbied on behalf of the pharmaceutical company and I thought it was amazing. All the things I can do from a legal perspective to help companies like Lilly bring drugs to market was just so powerful. My sister had leukemia, and I had the chance to see an experimental drug really impact her survival rate. Being able to bring those kinds of concepts to market – whether building, helping the company raise capital, or helping them work with people. If you work with the companies – changing the laws, providing the incentives, and helping find the capital – you can change so many lives. I went to law school in part because I wanted to further all these goals that I had from the science side.

Is Doxly your first startup? How did you make the leap into the startup world?

Doxly is my first startup. As an attorney, I helped counsel startups in terms of how to form their business, how to move their ideas forward, and how to raise capital. But from a career perspective, I was always a lawyer. I practiced for over 10 years, made partner, and had no visions of leaving the firm. I started creating little products within the law firm. For example, a startup company package of 10 documents you need to form a company. I would offer it for a fixed fee so that someone could form their business and still have the expertise of a great law firm, like Ice Miller. And then I looked into how we could help those companies find funding. I did more research on what investors were actually investing in and trying to match people with the right investors. I had this great book of business, but that also meant I was super busy. I was trying to manage my clients, work with the firm’s clients, trying to make partner, and I was pregnant with my second child.

I made partner and then told them about my idea for Doxly. I worked on it for probably about a year and a half. During that time, I began really thinking through what would it mean to start a company; What would I do? Is this viable? Would people be interested in it? Is it technically feasible to build what I was thinking of? I got paired with High Alpha and started working with them. I went through a Sprint Week that was designed to find viable business opportunities and Doxly was the winning idea. Originally, I was going to stay at the firm because I had just made equity partner, but I stayed on the board for Doxly. Then after about two weeks, I couldn’t imagine not doing it, so that was the point that I resigned.

Have you always had an entrepreneurial spirit or was it something that came to you later?

I think I did, but I wouldn’t have thought of it as entrepreneurial spirit, I just thought about it as how to solve problems. For example, I was a lifeguard and swim lesson instructor in our neighborhood. I was teaching lessons and there were kids that were doing really well, and they wanted a swim team. So, I got the pool to let me create one. I was the coach, I found teams for us to compete against, we hosted meets, I got volunteers – we put together an entire team. I didn’t think of it as entrepreneurial, I just looked at it as something our neighborhood needed and figured out how to make it happen. Another example is when I wanted to build business for Ice Miller, I created a startup company package. I’ve always wanted to solve problems, and I’ve learned that part of the entrepreneurial journey is seeing problems and thinking about how you can solve them.


Other than industry knowledge, how has your prior professional experience helped you as an entrepreneur?

There’s the scientific process of trying things and testing out hypotheses. That comes into play in terms of being able to pivot and think through different ways we could price, or different ways that we might get customers to adopt. From the lawyer side, it helps to not only understand the industry and the pain points that people have, but lawyers do a lot of research and they’re really thoughtful in terms of what they’re going to put together for people and how they’re going to approach a problem. When starting Doxly, there were so many business things I didn’t know about. The lawyer side of you says you research, you figure it out, you learn, you talk to someone, you learn the best that you can with the materials that are available. In law, if you run into a problem with a client, you don’t just let it drop. You have to figure out a way to learn about it. I think that that curiosity that lawyers have and that attention to detail and diving in to be able to figure something out really helps.

There are definitely downsides that a lawyer has in terms of being able to delegate. We’re so used to working on our own. If I have to give a document to someone else and then review it, sometimes I think I could’ve done that faster on my phone. But I can’t draft six documents. The company doesn’t work unless it’s a true team.

What are some of the biggest challenges you’ve had while leading a startup?

The biggest thing is understanding how to work well with a team. It was easy to understand that engineering would have knowledge on how to code things, and that I would never be stepping in their area. But I didn’t necessarily understand the full boundaries of what they were doing and why they needed to do it certain ways, and why we couldn’t shortcut. It took some time to get to know them and understand processes. Learning to be able to delegate was hugely important because you can’t succeed if it all falls to one person. You really need a strong team that builds on those weaknesses. Attorneys work so much on our own and we’re responsible for our own work. If an associate provides something to me that isn’t great, I still have to deliver something that is. So, you fix things, but you move so quickly, you don’t always spend the time to tell people how they can be better. If I decide that someone didn’t produce quality work, I would just work with a different associate. But if you can’t communicate what people need to do to improve, then you’re not really leading. They’re going to continue to do things in an inappropriate way until the point you have to fire them. You’ve never given them a chance to be better. Avoiding confrontation does not work in a company. I also had to learn patience in terms of how long sales cycles can take at complicated organizations that have huge security review processes. I had to understand that things can take a while and that we are going to have bumps along the way.


What has been the most rewarding part of founding and leading a startup?

Building a product that improves people’s lives and workflows is incredibly rewarding. I truly loved being an attorney. I liked working at a big law firm and I didn’t mind the long hours. I loved our clients and I loved what we were doing. What I was hoping to do with Doxly was to have a team build a product that people would enjoy using and that would make their experiences better. It’s so rewarding to hear that customers are able to do things faster with Doxly. I also get to work with incredible people who are passionate about what we’re doing. Being able to see them grow and move into great roles within the acquiring organization is really great to see.

Looking back on starting Doxly, what are some of the things you wish you would’ve done differently? Any mistakes you learned from?

It’s hard to say that you’d really go back and do things differently when you have a successful exit in three years. We had two successful venture capital rounds, great customers, a product that we were proud of, and we were really starting to hit our stride in terms of developing business. I could say that we could’ve focused on a particular area and we might have gotten more sales immediately. But would we have had the same success or exit in the end? I don’t know. We made a lot of decisions that led to a really quick outcome, so I don’t know that there is any one thing that I would change.

In leading Doxly, was there a point where you felt like things weren’t going to work out to plan? If so, was there something you could point to that helped you get over that hurdle?

So many times. I think you would be hard-pressed to find a startup where everything went according to plan, sometimes in a really positive way and other times in a negative way. Things are so unpredictable. To a certain extent, you can only plan so much. You have to be nimble to respond to challenges or bumps in the road. We learned early on that even with a known pain point and strong feature set, we would have to build credibility before law firms would trust us with their most sensitive deal data. That led to longer sales cycles and more pilots. We adapted our sales process, how we priced, and our thought leadership to account for some of these challenges.

Has support from organizations like Elevate helped you in a way that you felt was outside of expectations?

Elevate actually went above and beyond for us before they were even an investor. Mark Gramelspacher introduced us to one of our first strategic investors, NextLaw Ventures, before our first capital raise. NextLaw is affiliated with the world’s largest law firm, Dentons. Mark would later become a board advisor to Doxly and his experience in the legal space was really helpful as we worked to scale the business and ultimately exit.

Doxly was incubated out of High Alpha venture studio and subsequently raised a few rounds of financing. How has that path impacted Doxly’s development trajectory?

I think it is part of the reason why the trajectory is so fast. High Alpha provided a lot of the initial infrastructures. They did our original hiring, our employment plans, recruiting, finance, etc. All those things are important, but if you’re doing them alone, they distract heavily from figuring out what the product should be. So, it gave us the ability to focus on the core business while giving us the foundation that we needed in order to grow. They also started us off with a design focus so that the core of the product was well-designed. I think that helped people see the vision right away. They just taught us a lot. We had marketing help from day one. They helped build our websites. Scott Dorsey and Mike Fitzgerald helped me think through revenue models. Eric Tobias helped us set up and manage the product. I don’t think you can move as quickly as we did and build stuff as big as we did without some of these foundational things. They helped us on the capital raise side, too. We knew they’d committed to putting money in and we were able to tell a story together. All those things helped speed up the trajectory.

Congratulations on the recent acquisition by Litera Microsystems. How did that transaction come about?

We got a lot of inbound interest from companies that wanted to consider strategic partnerships and those quickly turned into acquisition offers. We had several different people that could see that we would not only be good partners but would be a good fit into what they were trying to do. We had started talking to potential acquirers when Litera came in to ask about a partnership. We were candid and let them know that we had already received interest. They were also candid with us in that they had acquired Workshare, which has a competitive product to us, but they were still interested.

We had another offer at that time, so we had to think through what the best outcome from a board, stockholder, and overall company and employee perspective was. One of the things we wanted was speed and certainty. I didn’t want to distract my team. I didn’t want an out, I wanted an outcome. Litera said they could do it within seven to 10 days and they did.

Given your extensive transactional experience, what are a few recurring themes that aspiring venture-backed entrepreneurs should know?
“Make sure you understand the problem that you’re trying to solve and that you are constantly in touch with your customers.”

Make sure you understand the problem that you’re trying to solve and that you are constantly in touch with your customers. I don’t think that can be understated. The amount of customer engagement you need to make sure the product you’re building is something that people want and is really solving their problems, not just a solution waiting for a problem. The more people can use your product and give you feedback, the better you’re going to be able to position yourself.

I was also always mindful of what that landscape was and how to build relationships and network. I would go to conferences and spend time meeting with people. If I ever was in a position where I needed to raise capital or figure something out, I had the network of people to go to. You cannot get locked into your office.

You have to leverage your team so that you can go out and build the landscape. We were able to raise capital faster and do the acquisition in large part because of the brand and the product we built. We did it as quickly as we did because we had organizational-like rigor. We focused on making sure that our financials were done well. So, when people came in and looked at our books, they weren’t uncovering some glaring issue. We had lawyers from the start so that our contracts would be okay. Since we’re a software business that stores information in the cloud, we had to deal with GDPR and data privacy. You can build this great business, but if you get to the point where you’re going to sell and your cyber security is at risk and your contracts aren’t put together, then you don’t look like a real business that they can really acquire.

You had been advising clients on capital raises and M&A transactions prior to founding Doxly. How have your perspectives changed now that you’ve been in your client’s seat?

It definitely changes. You understand more of what the investors are looking for. From our perspective, we understand the story our clients are trying to tell, and we can give them the guidance. It also changes things on the acquisition side. It gave me a new appreciation for our clients because we closed our acquisition deal in 10 business days, which meant I needed our attorney at Ice Miller, Eric Goodman, to work around the clock for us. And I’ve been in those moments where a client says, “Hey, I really need this by tomorrow.” And you wonder how they could be asking this of you. And now I get it. At some point I realized I was acting like a client and not keeping great track of everything – and I’m a lawyer and I know better. All those things that I used to preach to my clients, I saw how easy it was to forget them. You’re focusing on things that seem way more important to you in that moment; keeping your business going or being able to pay your employees.

For the M&A process, I think the biggest difference was the rollercoaster of emotions. Deals stop and start, and you have to run a business at the same time. I don’t think I appreciated the actual emotional and mental toll that an acquisition could take on you when it’s your company. As a lawyer, you’re just drafting the documents and doing everything you can to get to agreed terms, but at the end of the day, anything could happen that could derail it. We were also closing a really large deal, so I was trying to get through two major things at the same time. We had a couple of options on the acquire, and so I wondered if I made the right choice for my team. The board and I had decided that this was a great opportunity and we absolutely should do this, but everyone else was affected. Customers were affected – they wanted us to stay by ourselves. We had investors that were so excited about what we were doing, and they were thrilled with the outcome. Our employees were happy, but also wondering what would happen next.

Companies typically sell in five to seven years and we were three years in, selling the company and having a great exit. To a certain extent, while everything is changing, nothing is changing. We’re continuing to build exactly what we wanted to, to serve the customers that we had sought out. And now we’re just doing it on a totally different scale.

What’s next for you? What’s next for Doxly?

I’m now the general manager of transaction management for Litera. They have all their document drafting tools and they’re basically building another product line around transaction management. We’ll go forward with a product that we’re going to deliver to customers that hopefully meets all their needs from a global transaction perspective. Our whole team is coming along for it and being an integral part of what’s happening next.

Overall, it’s been a great process. We had great investors that helped us get there and they gave great advice. I think it’s important to have a good investor group that can help get you where you need to be.