This CLOC Talk episode brings together three seasoned legal operations leaders, Jenn McCarron, Co-Founder & CEO of Contracts.ai, Mary Shen O’Carroll, CEO, LegalEng Consulting Group and host Mark Ross, Principal and Growth and Markets Leader at Deloitte for a candid conversation recorded on the floor of CGI 2026. They reflect on the unexpected “right place, right time” opportunities, bold career decisions, and pivotal moments that shaped their journeys in a profession that was still finding its identity. Through personal stories, they share the lessons, risks, and opportunities that shaped their careers in legal operations.

Tune in for a must-listen conversation for anyone navigating the evolving world of legal operations.

Hi, everybody.

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Welcome to the floor of CGI 2026 and Clock

Talk, the podcast for legal operations

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professionals to stay connected, get

informed, and stay ahead of the curve.

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Today, I'm turning the tables.

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I'm absolutely delighted to welcome two

of my good friends, industry stalwarts,

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Jen McCutcheon, Mary Chenoweth Carroll,

for a conversation about their incredible

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careers in legal ops and beyond.

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Great to have you with us guys today.

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Great to be here.

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Thank you.

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Okay.

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I've got a number of questions,

knowing you guys the way I do.

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I suspect we'll get through one.

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Yeah, let's do one question.

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Yeah.

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We should be asking the questions.

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We're the podcast hosts here.

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Yeah, we're actually the podcast hosts.

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Tables are turned, guys.

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Yes.

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It's a three parter.

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You've had careers collectively,

in-house, legal ops, big law,

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legal tech, legal tech services.

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As you think through that career

trajectory, and it's been successful

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ones for both of you, has there been

a single moment where you've realized,

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"This is what I need to do to achieve

success and the leader I wanna be"?

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That's part one.

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Number two, is there anything that

you've had to learn along the way, or

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even unlearn, to have that success?

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And the third part, I know you've both

made incredible personal choices along

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those journeys, but also, how much

of your success is down to personal

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decision-making versus what has happened

with the evolution of the legal department

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as a whole, and that evolution rising

your respective career ships, so to speak?

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So a three parter.

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Oh, th- Lots to unpack.

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Yeah.

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I forgot all the questions.

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Yeah, that's a lot.

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But, but the last question, and I'll say

this especially in alongside Mary, I feel

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like I caught the wave on a long board.

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I was in the right place, right

time, working for Steve Harmon, as

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you guys founded Clock, and up came

the industry and I was on the board.

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So it was a lot of personal choices,

but it was a lot of serendipity.

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It was a lot of chasing these guys around.

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And you disagree?

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Mary and I disagree- Well, no, no, no,

no, no … within the first minute No, I,

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I, I totally agree It's a good podcast.

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I totally agree.

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However, I think that when there's

luck and serendipity, you put

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yourself in the position to be lucky.

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Yes.

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You know?

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Like, we've worked really hard

to see disruption in this space-

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Yeah … and you turn around and

go, "Oh, wow, it's finally here.

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It's all happening.

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We've been waiting for this for 20 years."

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We haven't really been just

sitting and waiting for a wave.

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No.

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We've been trying to push

for this for a long time.

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And so you are in the right

seat when the wave comes.

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Yeah.

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I do hear you.

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I'm gonna go slightly off script

and just pick up on one point.

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I remember- We, we don't do scripts.

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Yeah, we break them right away.

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I remember hearing former CEO of

Baxter, I'm, I'm blanking on his name

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right now, wonderful public speaker,

and he always talks about both in

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professional life and in one's personal

life about the secrets of success.

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And I can't remember all five, but three

of them are luck- Timing and mentors.

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Yeah.

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Yeah.

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And you've touched on three of

them- 100% … right out the gate.

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Yeah.

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By the way, he talks about-

100% … that luck and timing in

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your personal life- Yeah … as well.

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I always think with my wife.

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Yeah, score.

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If she'd met me five years

before she met me- Yeah

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she wouldn't have liked me very much.

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So here's this example.

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Mary brings CLOC to the geographic

chapters, and she's landing in New

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York, starting the geo chapter.

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It's January 2017.

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Mary puts out a blast to some

of these New York City CLOC

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people and goes, "Does anyone…"

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In December 2016- I remember … "Does

anyone want to present at the first

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inaugural CLOC chapter around legal week?"

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And little old Jen, who you didn't even

know who I was, was like, "I will."

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And Steve Harman let it happen and gave

permission, and I went in that room.

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It was standing room only.

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There were 60 people in there- Yeah,

first New York … at Google's offices.

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First New York meeting.

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First New York chapter meeting,

and I did a 30-minute presentation

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on everything I built and did

at Cisco for four years quietly.

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And you and Connie were

like, "Where have you been?

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Who are you?"

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Yeah, she said, "Where, who are you?

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Why did I not know you?"

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What, what, what are you on?

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There's been a few people in

this ecosystem that you meet for

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the first time, and you're like,

"How do I not know you, Jen?"

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Yeah.

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"You're so impressive."

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And- Jason Barnwell was another one.

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Barnwell was one.

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Yeah.

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And boom, that room, I interviewed

with all of those hiring managers

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for the next six years in

potential employment opportunities.

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And so it's like the wave

came, you guys picked me up.

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Well, and so maybe one of the questions

you asked somewhere in the many, many

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questions- Luck and timing, I know

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was what have you learned to be

successful or a leader or something.

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Yeah.

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I mean, a lot of it is you gotta

take the risk to put yourself

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and to go after what you want.

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Yeah.

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Uh, what I learned early on is, you

know, a lot of us who are really

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diligent, try to do a good job and

please our boss, and, like, do as you're

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told, and, God, I've done a really

good job on all the job description

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things, that doesn't get you anywhere.

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You have to go and get it.

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No.

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Put yourself out there- Do you- … and

go for the job you want and just-

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Do, do you think some of the- … it

doesn't come to you … do you think

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some of the risks that you've taken

you knew were risks at the time?

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Again, I reflect back on my

own and- For sure … moving to

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the US, I knew it was a risk.

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I was a practicing lawyer in

the UK, comfortable existence,

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married a California girl.

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Came over to the US and rode the

ALSP wave, back then the LPO wave.

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Yeah.

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But at the time, it just felt

like a decision I was making.

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I knew there was a gamble

involved, but I didn't really…

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Maybe I was too young, but I

didn't really think to myself,

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"Oh my God, I'm moving continents.

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I don't have a job.

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Let's just see how this plays out."

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Yeah.

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I don't know whether that

resonates with either of you.

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Yeah, of course.

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Yeah.

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So many risks.

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I mean- So, yeah, you know … I

moved to Los Angeles for a role.

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I left Cisco to go into

Spotify, which was so risky.

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Cisco was so safe, and Spotify was chaos.

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And these decisions you make, they're

hard, and they're uncertain, and

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you're like, "I could get exited.

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I…"

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All the things.

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But you take it anyway because

the industry was forming around

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us, and people were desperate

for legal technology and data.

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But yeah, that's a big

calculus in all of this.

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Thinking about what we've all had

to learn- Oh, yeah … to achieve

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success, and maybe even some

of the things, as I said, we've

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had to- Un- unlearn … unlearn.

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Yeah.

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Let's talk a little bit

about the skill sets.

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I know we all- we're all fans of Mr.

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Susskind, and probably read Tomorrow's

Lawyers, and I also think even beyond

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that, about the book his son's bringing

out, What Should Our Children Do?

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Mm.

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And about all the skill sets

that they're gonna need to live-

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Yeah … the successful careers.

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So talk to me a little bit about

things that you've had to learn on

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the journey, and maybe some habits

and things you've had to unlearn.

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I think we touched on a lot

of it, and you said it, right?

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Like, find mentors, find people who

actually care about your career.

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When you come to them with a question,

they don't just dismiss you or, like,

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they're actually going off at night

thinking about what you asked them,

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and they come back and say, "I was

thinking about your career, and here

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are some people I want you to meet."

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Those are the real mentors, and the people

h- that you can go to and really trust.

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I do think you have to

learn to take risks.

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I do think you have to learn to kinda-

Not care what happens and kind of hope

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for the best, and there's a little bit of,

like, I don't know, maybe I'm an optimist.

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I've always thought what

could possibly go wrong?

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What's the worst that can happen?

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And if you believe in yourself and,

like, think that you're smart, if I

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can just get in the door, if someone

can just take a chance on me, I know

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I am good and I know I will succeed.

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I'm also just hard-headed

and I'll push my way through.

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So if this doesn't work out,

there's gonna be something else.

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I don't know, maybe that's optimistic,

but I- Well, that's a real- … I've

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been willing to take those chances

… that's a risk appetite that a lot

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of people don't naturally have.

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You naturally have it.

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Yeah.

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And then you were drawn to companies

and roles that let you come in

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and hard-head your way through.

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Yeah.

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But, like, you learned how to learn.

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You know how to drop into any

situation, learn the inputs,

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learn the outputs, and solve.

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That's a good point.

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And that's like a- That's

a really important skill

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really important skill- Yeah … to

do- Figure it out … all

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of these roles in this room.

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You have to drive your own learning.

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No company's gonna teach you what- No,

it's up to you … legal ops needs.

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You're the one legal ops person.

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You were the one legal ops person.

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Yep.

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And then they gave me

outside council management.

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I have no idea- Yeah … how to do that.

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It's all this.

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Yeah.

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Like, I always tell young people,

the imposter syndrome, everyone's

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like, "Oh, I have imposter syndrome."

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I'm like, "Kill that."

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Yeah.

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That is total BS.

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I know we can't swear on this.

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Sure.

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But you should always believe that

if somebody hired you or somebody

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gave you that task or someone gave

you that responsibility, of course

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you can do it, and you can do it

better than anyone else around you.

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Of course.

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But I also think in the profession,

certainly when I practice law,

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I think about my training.

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My training as a practicing lawyer was to

be risk adverse- Yeah … to study risk.

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Yeah, I didn't get that luck.

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You're talking to non, non,

air quote, "non-lawyers" here.

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We're like, forget that.

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Jump off- You know

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the mountain.

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Yes.

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I, I followed your way of in

thinking through, you know what?

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Yeah.

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There's a career for me outside

of traditional legal practice.

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Yeah.

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But things like program management,

change management- Oh, yeah.

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Those are like- All of that … core

skill sets Hard, yeah … they

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were totally alien to me-

Yeah … as a practicing lawyer.

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No.

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Never came- Yeah … into my day-to-day.

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You know, and those are things

that, candidly, I never touch,

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clearly, the practice of law anymore.

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Yeah.

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But I'm thinking about those

issues day in, day out.

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So how did you learn those things?

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I think by just throwing myself-

On the job … in the deep end.

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Like, nobody- On the job.

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And it is- Yeah, that's

right … it is sink or swim.

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And no one sits you down and

says, "Here's how we think about-

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No … change management here."

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On the job.

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Right.

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Well, learn.

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Now you can use chat, but we were using

the internet and YouTube and researching

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program management principles online, and

on the job training and curiosity and a

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willingness to drive your own learning.

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No company is gonna give you it.

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They're gonna give you the job,

and knowing how to drive that.

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It was the number one thing I

filtered for in hiring at Netflix,

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was can you drive your own learning?

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'Cause I can't train you.

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We can teach, we can

mentor, we can manage.

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Awesome.

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Well, again, before we wrap up, we've

got a couple of thousand legal operation

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professionals, legal technology

vendors, services providers here.

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As we look into our respective

crystal balls, dare I say that we

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may be in the OG group of legal

ops leaders and professionals.

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I think I'm round two.

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You're round two, Jen?

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Yeah, I'm generation two.

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Generation two.

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Yeah.

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I'm the old folks.

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You might, you might be OG, Mary.

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Oh, I'm Justin's old.

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As we think about the next generation

coming through, and then also as we think

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about our kids, what we want them- Yeah

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to do within legal and beyond, some

top tips from both of you guys, please.

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First, I am so jealous of the

people who are entering their

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careers at this moment in time.

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Yeah, with these tools.

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God, I wish I- With AI … had,

like, a runway in front of me now.

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I mean, I'm obviously at the tail

end of my career, but God, if you're

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starting and you're naturally curious,

like, the world is your oyster.

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Yeah.

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That's amazing.

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AI can write you your first draft of

your first strategy, and you practice

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that enough, and you can get in

front of your leadership and start

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to signal to them, "I can do this.

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I know what I'm talking about, even

though I'm putting it together, and

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I have the power of a big community

behind me," that's a powerful tool

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set to give you the first draft of

your slide, your legal ops remit.

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We figured it out, and we

called one another incessantly.

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Now we'll call each other less.

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We'll ChatGPT more.

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But I think we'll get, in the individual

roles all these folks have, I think

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they will get further faster- Oh,

yeah … with today's tools with AI.

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I'll, I'll finish up with

just an amusing anecdote based

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on your first draft comment.

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Literally this morning I woke up to

an email in my personal email from my

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wife to my 14-year-old son's history

teacher Apologizing on his behalf for

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his flagrant use of AI- Yeah … in the

crafting of an essay that was submitted.

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Oh, yeah, then there's that.

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Yes.

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Oh, I actually think kids should use AI,

and the school should be teaching them how

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to think and use it in a different way.

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I, I agree.

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Learn to think first and then

use it to augment your thinking.

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Yeah.

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Don't use it to think.

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That's where this can all become a crutch.

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Or please don't use it to write

your LinkedIn posts anymore.

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There's too much- Oh,

my God, please don't.

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Yeah … too much fluff,

and there's too much rhythm.

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It's not this, it's not

that, just the data.

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We all know you used AI,

and we stopped reading.

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Please get back to writing human,

human-feeling words- Yeah … and

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we'll rally in the comments.

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But creativity is also really important

right now in addition to the initiative.

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So if you have all these tools,

don't wait for permission again.

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Yeah.

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Go look out there, see what is

broken, and then just go fix it

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without being asked and told to do so.

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Then you will prove how good and

how useful you are and go for it.

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Well, I can finish up by saying

that no AI was used for the

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creation of this podcast today.

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Yes.

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This was creative brilliance at its best.

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Jen, Mary, thank you very much.

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This was a lot of fun.

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Thanks, Marc.

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Such a pleasure.

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Good to be back.

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Take it easy.