3 Lessons I Learned in My First Year as CLO

Dear 2025 Ariel,

You did it, girl! You worked hard and got your dream job but now what are you going to do with it?

— Letter to Myself, April 18, 2024

Day 33 as CLO of Insight Global

Have you ever had that feeling? When you worked so hard to achieve something that you wanted more than anything?

Maybe it was a degree, or a personal fitness goal.

Maybe it was your dream to become a parent.

For me—at this point, at least—it was my dream job.

But then the work is over. You’ve done it. You’ve reached the top. Then what?

The time and effort you devoted to actually achieving the goal is no longer needed and now it’s time to DO THE THING. Then that “what now?” feeling starts to creep in.

It’s a daunting feeling that can leave you full of self-doubt.

Are the people I am leading going to take me seriously?

Are my peers?

Do they believe in me?

Do I believe in myself?

My old boss David Lowance used to tell me I have a “Type A+ Personality” (which is a nice way of calling out my control-freak, high-achieving tendencies). Having a Type A+ personality amplifies the fear of failure when you start something new, big, and scary.

But as I reflect on my past year of CLO, I’ve learned a few things that will help you if you are pursuing your own new, big, and scary dreams:

Growth and Comfort are Incompatible
Surround Yourself with People Who Are Smarter Than You Are
Do It Your Way

Let me break down what I mean.

Growth and Comfort Are Incompatible

When you step into something completely new, you can’t do things the way they’ve always been done. Yes, some foundational things that have always worked will remain—but stepping up to be Insight Global’s Chief Legal Officer was an opportunity for me to bring my unique talents to the role.

Our executive team wanted a CLO who was strong, different, a risk-taker, and a true business partner. A CLO who could let the business expand into new countries, nimbly pivot into new business lines, and fight for the company. No problem—I’ve got that covered. But executing those goals required me to step outside of my comfort zone and grow as both a leader and a lawyer.

I think of the groups within the CLO organization as the protectors and defenders of the company:

Contracts red-lines, negotiates, and catalogs agreements to protect us from legal risk.
Security not only protects our physical office spaces and employees but also protects U.S. national security through the management of security clearances.
‍Legal ensures our compliance with laws and regulations, protects the company from legal and reputational risk, and defends the company in legal conflicts.

How would I inspire my team to be bold, take calculated risks, and think outside the box? We needed to adopt a mindset of being business enablers while still doing our jobs as business protectors. It wasn’t going to be comfortable—but growth and comfort are incompatible.

Surround Yourself with People Who Are Smarter Than You Are

A leader who thinks that she knows everything is a leader who is destined to fail.

When you lead a multi-disciplinary organization, there is no possible way to be an expert in every discipline you lead. The key is to surround yourself with trusted subject matter experts and leaders who know and own their worlds. The best leaders do this while remaining curious, thoughtful, and humble enough to learn the things you need to know.

I am incredibly lucky to have a team of senior leaders who help me lead the variety of subject matters under the CLO umbrella. Not only do they bring years of experience and credibility to the functional areas they lead, but they are dedicated servant leaders to their people.

Earlier this year, we held our Compass with the goal of defining: 1) what our people needed and 2) how we were going to lead.

(Compass is a two-day leadership retreat that goes beyond traditional team-building exercises, allowing for team members to connect to each other, to their purpose, and to results. We hold these internally, but we also host Compass as a service.)

Coming out of that experience, our vision is clear: We are turning obstacles into opportunities so our people can dream big, sell bigger, and deliver with confidence. This vision represents the pivotal role that our teams play in support of the business, and how we view ourselves as true partners. I am proud to work alongside these talented leaders and am grateful to have learned that I can’t possibly know everything, but I can surround myself with experts who own their worlds.

Do It Your Way

I wear Nikes to work. I fan girl over Dolly Parton and Ruth Bader Ginsburg equally. I take figure skating lessons. I say what I think even if it is an unpopular opinion. I’m loud, a professional hand-talker, and fiercely loyal. Most importantly, I’m not trying to be someone that I’m not.

Before I came to Insight Global, I was a litigator in private practice. What does that mean? I went to court. I took depositions. I tried jury trials. I OBJECTED!

Litigation was then, and is still, a male-dominated industry. Lots of machismo and pounding on the table, being jerks to the guy on the other side, trying to show what a bulldog you are. The partner I worked for at the time really embodied all these litigator stereotypes. When I was coming up, he wasn’t necessarily teaching me how to be a lawyer in my own skin; he was teaching me how to be his carbon copy. Did I pound the table hard enough? Did I interrupt the lawyer on the other side frequently enough? Was I being him?

Frankly, it was painful for me.

Trying to be someone you’re not just doesn’t feel right. In the beginning you think it will be okay… that in a couple of days, or weeks, or months, it just won’t bother you anymore and you’ll adapt. But the reality is that it will always bother you. And you know what else? When you are trying to be someone you’re not, you are not showing up as your best self.

I bring my whole self everywhere I go.

With me, what you see is what you get. I don’t have a “Work Ariel” and “Out of Work Ariel.” It’s just one me, and I’m here for it.

I’ve been in the “game” for a minute. Since 2007 to be exact. It took me a long time to feel comfortable showing up as my whole self. But it also took me a long time to find Insight Global. One of the most beautiful things about Insight Global is that showing up as my whole self, and doing it my own way, is celebrated. There is absolutely no expectation that I should act a certain way because of my position or because that is what my predecessor did.

I know that I am in my position because I act like me, and that is enough. That is the expectation. And that expectation is a gift.

So, as I reflect on my year in the role as Insight Global’s Chief Legal Officer, I am grateful. Grateful for the lessons learned: