Meet Leslie Olsen: A fireside chat with Ontra’s Chief Marketing Officer

March 27, 2024
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What was your main motivation to join Ontra?

There are always a number of criteria I consider when joining a new company, but the most important is the people. Do I want to spend most of my waking hours with this group of people? Will we be able to both push each other to a higher level, and have a good time doing it? When I met the first few folks at Ontra, I was immediately struck by the universal characteristic of high IQ + high EQ. That is exceedingly rare and was a huge draw for me.

Second, I look for a clearly articulated company strategy combined with a bold product vision. Troy Pospisil walked me through both in our first meeting. It’s not unusual for the CEO to be able to clearly communicate strategy and product vision, but what is less common is to hear it echoed so consistently across the entire leadership team. For me, this clear and consistent vision demonstrates commitment and alignment across an organization, and this was incredibly important to me.

Having said all this, what ultimately drew me to Ontra was the energy I felt every time I spoke with someone on the team. The excitement about where the company is going is absolutely palpable. You can hear it in the words, see it on the faces, and sense it in the room. I wanted to be a part of that.

How would you define your role as CMO?

I see my role first and foremost as the Chief “Market” Officer, with a laser focus on the market, the competitive landscape, and most importantly, our customers. It’s also my job to ensure this market intelligence is shared and well understood across the organization. Getting to this level of understanding requires a deep and constant focus on the customer to pinpoint what is important to them, what their challenges are, and how we can better serve them.

Understanding the customer also means understanding the overall customer experience, starting from the very first moment they become aware of Ontra to all of the many moments that lead up to a long-lasting and trusted relationship. I see my job as both making the brand promise to the customer (articulating what value we will deliver) and then ensuring we keep that promise over time by partnering with all the internal functions that touch the customer.

And, of course, I’m here to drive revenue growth, and to ensure the marketing function as a whole is delivering concrete business impact and outcomes. We can and should be able to map our efforts and activity to core business metrics. This rests on a foundation of data, analytics, and experimentation, as well as the development of a marketing culture where we combine that deep customer understanding with qualitative and quantitative insights. That’s where the magic happens.

Describe how your career trajectory led you to this position.

From a career trajectory perspective, it was really my first internship out of college that put me on this path. I was hired into a high growth software company to support the channel marketing team, which sat within the channel sales organization. I learned early on the importance of aligning closely with sales and the stresses of carrying a quota. I think it was my overall curiosity about people that led me to spend my formative years in product marketing and product management, which ingrained in me a deep customer obsession and an emphasis on measurable and tangible results.

Can you share any personal anecdotes or experiences that have shaped your journey as a leader in marketing, and how they have influenced your approach to leadership?

I can tell you about a number of early experiences that shaped my journey as a human, taught me lessons that have stayed with me, and ultimately led me to a leadership role in business. I have always been drawn to activities that are new, challenging, and outside of my comfort zone. At 19, I decided to do a two-week mountaineering trip on Mount Adams. Although I was an athlete in high school and outdoors a lot, I had never been camping. At 20, I decided I wanted to study abroad in Paris, but my university didn’t have a semester program, so I created my own program and went to school as a French student. At 21, I decided I wanted to take a year off post-undergrad and live in a ski town in Idaho.

What I learned from each of these experiences is that I like to push myself — hard. And I like to surround myself with people who also push themselves. Some additional learnings have stayed with me: On Mount Adams, I learned about making tough decisions when one of our team experienced severe altitude sickness on our summit attempt. We could have split up with one group summiting, but ultimately it was more important to stay together as a team. In Paris, I learned that at times you have to set aside your pride and sound stupid in order to learn something new (a new language, in that instance). And in Sun Valley, I learned that you have to take advantage of opportunities as they are presented, when I was offered the manager role at the restaurant I’d been waitressing at for 2 months (don’t worry, this did not cut into my skiing hours).

All of these have informed my leadership style, but ultimately, my style is a direct reflection of how I like to be led.

I want to feel like I have the trust and autonomy to do my job. I expect to be held accountable for my areas of responsibility. I want to feel like I have deep personal connections and real relationships with the people I work with. I want to be able to be my true self at work. And, I want all those who work with me to feel the same.
Leslie Olsen
Ontra Chief Marketing Officer

How do you perceive the current state of our industry, and what trends do you foresee shaping it in the near future?

I’ll speak to private markets first, where I’m just beginning to develop an understanding of trends and drivers in the industry. I’ve spent the past few weeks trying to absorb and learn as much as I can. Now that I know what to look for, it has been surprising to me how ubiquitous private equity is across financial markets and the broader economy. It was there all the time, but without the context, I didn’t see it clearly — now I can’t unsee it.

There are many signals that the industry is at an inflection point, with the confluence of many factors — growth and diversification, competition, regulation, and overall economic conditions. Not to mention the emergence of new transformative technologies. It is during these times of intense change that disruption and innovation thrive. People are more willing to scrutinize the status quo and are open to exploring new and better ways of doing things.

I can also speak to trends in the enterprise B2B market, which has also been in a phase of enormous transformation. Most interesting has been the change in buyer behavior over the past several years. B2B enterprise buyers are now spending the vast majority of their time researching and investigating solutions on their own, anonymously. They are far down the decision-making path before they engage with a seller.

This dynamic makes go-to-market (GTM) alignment absolutely critical. Sales, marketing, and customer success need to be attached at the hip to win in this environment. The GTM teams need to collectively read and understand the signals that indicate who is actually in-market and what they are interested in. This alignment allows GTM teams to develop messaging and content that effectively influences the research journey, so when our buyers are ready to talk, we’re the first on their list to speak to.

What is your vision for the company’s marketing efforts in the short and long term?

As I’ve gotten deeper into the inner workings of the Marketing team over the past couple of weeks, I’ve been really excited to see the great work already happening. The team has been through its own transformation over the past year, with many new functions and leaders. From a foundation perspective, we’re going to continue down the path of developing deeper customer understanding. And, we’ll work to layer on a more comprehensive view of the touchpoints that increase conversions (through to closed won deals) and accelerate the sales cycle.

Top of mind for me is the opportunity to create a more holistic company narrative and really tell our story. We have a strong foundation to build on with our vision for the Legal Operating System. We can clarify exactly how the Legal Operating System will take shape and how it will be transformative for our customers and the market. We can also better emphasize our core differentiators, reinforce the tech-forward nature of the business, and continue to drive home the fact that we have an incredibly impressive customer list — by far the best in the industry.

Lastly, I’m excited about the opportunity to be even more targeted and personalized in our outreach. I’d like to see the majority of our outreach triggered by signals that allow us to hit the right person at the right time with the right message. Many of these signals are used today for sales outreach, so this will drive even tighter alignment. I also would like to extend personalization through to our customer communications, leveraging product usage data to remind them how much value they are getting from our products. Ultimately hyper-personalization is the goal across the board.

From your perspective, what is the biggest opportunity ahead of Ontra that has yet to be unlocked?

To be very candid, I think the biggest opportunity ahead for Ontra is to stay focused and execute the sh*t out of our strategy. I’m not saying this has yet to be unlocked. But, staying focused is one of the hardest things to do in a tech company. Stay focused, and we will achieve our vision: A world where private market professionals are free to focus on what’s important to them.

I am confident this team can do the hard work of staying focused and executing flawlessly. This is a team with talent, discipline, and alignment, laser-focused on bringing the Legal Operating System to life, where we become embedded in the daily workflows of our private equity customers. Where we enable the best private equity firms in the world to optimize their legal operations, and more importantly we give them a massive competitive advantage in an industry where speed and accuracy win.

What do you enjoy doing outside of work?

My world revolves around my family, and I wouldn’t have it any other way. I live in a crazy household with my husband, 3 kids (17, 14, and 7), our Australian labradoodle, 3 tetras, and a 3,000-year-old hermit crab (ok, slight exaggeration there, but he’s been with us for a long, long time). My parents live about a mile from us, and my twin sister is about 10 miles away. I never know who is in my house at any given moment.

Weekends are absolute chaos, usually running from one kid activity to another. Sports, Girl Scouts, shuttling teenagers to movies, you name it. If we don’t have kid stuff happening, you’ll often find me outside — hiking, walking, gardening, running. We’re also a big ski family, so we get up to Tahoe as often as we can.

If none of the above is happening, you’ll find me curled up with a book, working to escape for a bit and recharge for the next activity.

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