Ontra employee spotlight: Kathryn Caterina

October 17, 2022
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As one of Ontra’s earliest employees, Kathryn Caterina has experienced many aspects of Ontra. In fact, she started out as one of Ontra’s legal partners and now is directly involved in ensuring Ontra customers reap the full value of our platform and services. When she’s not leading account managers and company initiatives, Kathryn might be chasing after her preschooler or enjoying the many cultural experiences Los Angeles has to offer.

In honor of Hispanic Heritage Month, Kathryn shared how she landed at Ontra, how her Hispanic heritage influences her, and all the ways Ontra supports Kathryn in bringing her full self to work.

Like many of your colleagues, you came to Ontra after working in the law field. What attracted you to Ontra and why did you decide to make the leap?

After practicing corporate law at big firms for eight years, I ultimately realized the work culture and lifestyle weren’t sustainable for me. BigLaw tends to demand lawyers prioritize work before themselves and their families and friends. I was disillusioned but knew there weren’t many alternatives for someone with my background. When a friend, Frank Giovinazzo, Ontra’s general manager of Contract Automation, told me about Ontra and its plans to improve the legal industry, I was inspired. 

At the time, Ontra was unique in offering the opportunity to be a part-time transactional lawyer working remotely with sophisticated clients. Just as exciting, Ontra was systematizing the negotiation of agreements in a way that no other major legal service provider was. Like all of our initiatives, Ontra was taking simple yet revolutionary steps to improve the contract negotiation experience for everyone involved. Since law firms are slow to adopt new processes, the fact that Ontra was innovating on this level struck me as very smart.

After a couple of years as a legal partner servicing Ontra’s customers, I was so energized about our mission that I transitioned to a role on the account management side of the business.

What changes have you seen since joining Ontra in 2018, and how has Ontra helped you and your colleagues adjust to these?

When I joined the account management team, I was employee #17 at Ontra. I recently celebrated my four-year anniversary in that role, so I’ve seen quite a few changes. 

When I started as an account manager, Ontra ran just two small offices. I was the third employee in the Los Angeles office. At that time, we were a scrappy, nimble team of professionals from various disciplines. We were in constant communication, and it felt like a single team rowing organically in the same direction. 

Since then, the company has scaled more than tenfold, and our employee roster feels less like a singular team and more like a diverse group of teams that are somehow still rowing in the same direction thanks to the capable leadership of our C-suite and department heads. We’ve formalized more processes, which is necessary as a company grows. But the mission remains the same and is very clear: to make contract processes more efficient, and to free business professionals and lawyers to focus on impactful work. Our mission is reflected in our company values, and the leadership team does an amazing job encouraging us to keep our eye on the ball and to row in the same direction.

In your role as managing director, how do you ensure successful relationships between customers and Ontra’s curated legal partners?

Account managers are the glue between Ontra’s customers, legal partners, and technology services. There is a natural tension there, but at the same time the success of one is dependent on the success of the others. The best decisions we make as account managers are the ones that take into account — and ideally have a positive impact on — our customers and our legal partners. Getting to that place often requires  a variety of skills such as active listening, creativity, mediation, and advocacy. Most of those skills are learned by experience and cannot be taught in an academic setting, so that is a large component of my coaching of other account managers as well.

What does Hispanic Heritage month mean to you?

I love my Mexican heritage, and the culture that my grandmother and grandfather brought with them when they emigrated to Texas in the 1950s. Many Americans are simply unaware of our rich and complicated and beautiful history, and I would also go so far as to say that many have very negative associations with Mexico and other Latin American countries. This time of year, during Hispanic Heritage month, I’m excited to share the beauty and richness of cultures that come from those places too. 

For instance, I love the tradition of Dia de los Muertos, or Day of the Dead. The skeleton imagery can make it seem scary or macabre, but it’s really the opposite. Who wouldn’t like the idea of being present with and celebrating the memory of loved ones with such color and joy? I find it so touching and meaningful.

How has your culture influenced or inspired your work/leadership style?

I come from a long line of very strong matriarchs who were responsible for big families and never questioned their own capabilities. The women in my family have never let challenges slow them down. Instead, they’re doers, and I think there’s a cultural component to that. I carry on that tradition at work by pushing the mission forward rather than being influenced by fear or dwelling on what we can’t do. 

What does Ontra’s mission and culture mean to you personally?

I deeply care about making sure that Ontra enables people — not just our people, but our customers and legal partners too — to thrive. I have experienced this myself as someone who partnered with Ontra as a lawyer for two years following my career in BigLaw and before joining the business team here. When you give people time and space to focus on what is important to them — which is core to our mission — they are able to be more present not only for more impactful work, but for their friends and family and, most importantly, themselves.

Ontra’s CEO Troy Pospisil once asked me what my ideal job would look like. I replied that I wanted three things: To believe in what we’re putting out into the world, to respect the people I work for, and for them to have respect for me. I have found all of that and more at Ontra, and I’m committed to making sure my colleagues experience that also.

Moving from law to Ontra wasn’t your first big leap. What prompted you to switch gears from music to law, and what’s your involvement with the L.A. Choral Lab?

I’ve been involved in the music world my entire life: my upbringing was steeped in choral music, and I have a bachelor’s degree in Music Industry from the University of Southern California. At some point I made a conscious decision to step away from it to pursue law, which ultimately is a much better fit for me professionally.  Then a few years ago, the L.A. Choral Lab, an innovative, semi-professional choral group in Los Angeles, invited me to join its board of directors. It has been invigorating to step back into that world and combine my professional perspective and musical background. That experience has inspired me to hopefully join a community chorus, which I can actually do now because Ontra provides me with a lot of autonomy over my schedule. 

As it turns out, there are many current and former choral singers at Ontra. There have even been rumors of forming an account management quartet, so stay tuned!

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