Ontra employee spotlight: Rich Niles, senior software engineer

January 14, 2022
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What do a mathematician, self-taught programmer, entrepreneur, and grandfather of two have in common? They are all titles proudly held by Rich Niles, a senior software engineer at Ontra since the company was founded in 2014.  

Rich, arguably one of the most impactful contributors to Ontra’s success, is hanging up his hat after an illustrious, five-decade career. His career highs include the founding and successful sale of EndNote, a reference management tool for academics, and stints at UC Berkeley, Stanford Research Institute, and UC San Francisco.

Rich sat down to discuss his journey to Ontra, why the work he’s done to develop the company’s contract automation and intelligence solutions ranks among his top career accomplishments, what he’ll miss most about life as full-time employee, and, perhaps most importantly, the ways he’ll spend his newfound free time. 

Rich, you’ve had quite the career. Can you tell us about the big stops along the way?

Originally, I wanted to be a mathematics professor so I got my PhD in mathematics and taught a course at UC Berkeley. Unfortunately, it only lasted two years because everyone at that point believed that finite group theory had been solved by a guy at Caltech. Though I knew this wasn’t the case, no one was hiring in this field and so I got into computers. Despite knowing little about computers or programming (this was during the 1970s, well before computer science classes), I found a job where someone was willing to teach me how to program. 

I ended up doing research on a classified subject at SRI International (formerly Stanford Research Institute) for five years before striking out on my own to do consulting. During this time, I also wrote accounting software for various clients. My wife, a virologist at UCSF, was plagued by the painstaking task of creating bibliographies at the end of her grant proposals. To alleviate her of this required but burdensome task, I offered to write a program that would create bibliographies for her. It wasn’t pretty, but it did what it was supposed to do. Eventually I realized this could be a viable product and hired a couple of guys to work on it. This project ended up becoming EndNote, which I ran for 11 years before selling it in 1999.

What brought you to Ontra? 

Following the sale of EndNote, I spent seven years as a programmer at UCSF. Afterwards, I entered a semi-retired state, which I found extremely boring. At someone’s suggestion, I began learning Ruby on Rails to pass the time. In an effort to fully absorb the world of web programming, I also attended various local meetups, where I eventually introduced myself to two guys named Lane Lillquist and Gerry Cardinal. Lane, who was VP of Engineering at Uversity, Inc. (now TargetX) at the time, was looking for programmers willing to learn. The rest, they say, is history. Lane eventually left to co-found Ontra, which was known as InCloudCounsel back then, and eventually brought Gerry and me along for the ride. 

You’ve been at Ontra from the start. What are your top moments with the company?

I’ve had various highlights over the past seven years, but the top spot easily belongs to the development of our PDF viewer. Troy, Ontra’s founder, had the idea to hyperlink our NDA scorecard and the document being scored so that the answer is recorded on the scorecard when answered on the document despite being on separate screens. We unanimously, and famously, responded that it was impossible. However, after finding a package that made it doable, I eventually created our first version of the PDF viewer. We didn’t show Troy until it was pretty much done, but I’ll never forget his reply—an incredulous, but joy-filled, “You did it?!” You know, I even worked on this project at night because I loved it that much. 

What will you miss the most about working at Ontra?

The people, hands down. I have loved working with everyone, even beyond the engineering organization simply because the people here are brilliant and I like working with really smart people. I’ve been here since it was a humble, two-room office with a total employee number that I could count on both hands, and though Ontra has doubled year over year for the past two years (and continues to grow at breakneck speed), it has stayed true to bringing on intelligent, curious, and kind individuals across the board. 

What do you look forward to in your next chapter?

I’ve gotten to a stage in my life where I have grandchildren— a three-year-old and one-month-old—and I absolutely adore being with them so I’ll spend a lot of my time doing that. We also bought a house in Tahoe where I’ll spend summers and winters. To be honest, I’m  looking forward to being more active since I’ve typically been limited to exercising on one end of the day or the other. Doing stuff in the middle of the day sounds amazing, as boring as that may sound. But so does spending time with my wife Lenore and picking up on some photography. 

Any parting thoughts?

I am proud of many things I’ve accomplished through the years—like proving and publishing a theorem as a mathematician and successfully selling EndNote—but creating the impossible with Ontra’s PDF viewer is among the top five of my career and I’ll always cherish that.

I’ll end by saying that I joined Ontra as a software engineer because I wanted to, not because I needed to. I could have retired after selling EndNote, but I truly enjoyed working with the people at Ontra. Being a part of this team has been a pure joy so it is definitely bittersweet to say goodbye.

Thank you, Rich, for your endless support, tireless hours of development, and unwavering loyalty to Ontra. We will miss you.  

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