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EP 36: From Paralegals to Legal Ops Leaders: Tommie Tavares-Ferreira, Cedar, and Tom Stephenson, Legal.io image

EP 36: From Paralegals to Legal Ops Leaders: Tommie Tavares-Ferreira, Cedar, and Tom Stephenson, Legal.io

S3 E36 · The Abstract
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68 Plays6 months ago

How do you transition into a legal ops role? What are the new and exciting opportunities for legal professionals without a law degree? How will the legal operations community trailblaze a path for in-house counsels and law firms into the future of business?

Tommie Tavares-Ferreira, Head of Legal Ops at Cedar and Tom Stephenson, Vice President of Community and Legal Ops at Legal.io, have an expert understanding of both the legal ops industry and the diverse channels that professionals can take to arrive in the field. Not only are they the hosts of the Dear Legal Ops podcast, but they have arrived via their own journeys from big law firm paralegals and HBO contract manager to running legal ops at major businesses like Credit Karma, Rakuten, and Peloton.

Hear Tommie and Tom as they discuss the benefits for ambitious professionals to transition into a legal ops role, how to balance your business skill set with a strategic legal mindset, career paths beyond legal ops, and much more.

Read detailed summary: https://www.spotdraft.com/podcast/episode-36

Topics:
Introduction: 0:00
Transitioning from paralegal to legal ops: 2:30
Coming into legal ops from a contract management background: 5:22
Shifting your mindset from legal specialization to business strategy: 8:38
Debating whether legal ops is the right career path for everyone: 12:38
Establishing trust with stakeholders across the broader business: 15:50
Managing a legal ops department: 19:10
Maintaining a strong relationship with your general counsel: 23:59
Balancing your business expertise with your GC’s legal strategy: 31:01
The importance of placing the head of legal ops on the GC’s leadership team: 36:04
Considering career moves beyond legal ops: 38:48
Transitioning from legal ops to executive roles: 43:15
Presenting at CLOC 2024: 49:11

Connect with us:
Tommie Tavares-Ferreira - https://www.linkedin.com/in/tommie/
Tom Stephenson - https://www.linkedin.com/in/tstephenson1/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn

SpotDraft - https://www.linkedin.com/company/spotdraft

SpotDraft is a leading CLM platform that solves your end-to-end contract management issues.
Visit https://www.spotdraft.com to learn more.

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Transcript

Tom's Multi-tasking Antics

00:00:00
Speaker
I'm going to answer you, but I'm also going to say when Tom was talking about having a dinner and doing a podcast and doing accruals and doing an MSA, my mind made like an AI photo of all those things happening at the same time where he's at the dinner. He's got a mic in his hand. One hand's doing accruals. One's doing the MSA. Just doing it all over there. So is an octopus your spirit animal, Tom? I have eight tentacles, and they're just trying to figure out where to go.

Spotdraft Sponsorship

00:00:42
Speaker
The abstract is brought to you by Spotdraft, an end-to-end contract lifecycle management system that helps high-performing legal teams become 10 times more efficient. If you spend hours every week drafting and reviewing contracts, worrying about being blindsided by renewals, or if you just want to streamline your contracting processes, Spotdraft is the right solution for you.
00:01:03
Speaker
From creating and managing templates and workflows, to tracking approvals, e-signing, and reporting via an AI-powered repository, Spotdraft helps you in every stage of your contracting. And because it should work where you work, it integrates with all the tools your business already uses. Spotdraft is the key that unlocks the potential of your legal team. Make your contracting easier today at spotdraft.com.

Introduction of Guests

00:01:30
Speaker
What do you need to know if you want to transition into a legal ops role? How about finding success once you're in the role? And where can legal ops lead your career long-term? Today, we are joined on the abstract by two of my friends and leaders in the legal ops space, Tommy Tavares Ferreira, head of legal ops at Cedar, and Tom Stevenson, the VP of Community and Legal Ops at Legal.io.
00:01:59
Speaker
Tommy previously led LegalOps for Peloton and Tom led LegalOps for Credit Karma. They also have a podcast together called Dear LegalOps. If you haven't listened to it, you've got to check it out, which I happened to be a guest on last year and now they kindly agreed to join the abstract. Tom and Tommy, thanks so much for joining me today. Thank you so much for having us.
00:02:24
Speaker
Thank you, Tyler. It is such a pleasure to be on the other side of the microphone.

Tom's Career Journey

00:02:30
Speaker
We've got a few themes that we want to talk through today. I want to start by asking you about the transition from being a paralegal to legal ops, and legal ops is a little bit of an emerging field. Tom, I want to ask you first, this is a path that a bunch of other folks have taken. You started as a paralegal, now you run legal ops. What was that transition like? How did you make it happen?
00:02:56
Speaker
It was a long, long walk during some cold, cold days in Chicago, honestly. When I think and I look back at my journey over time, I actually started off as a legal receptionist in Chicago. I physically walked in after answering a Craigslist ad and I said, I'm not sure what I'm going to do, but I should figure this out at some point.
00:03:20
Speaker
during the great recession, you know, back in the early 2000s, I really was actually just grateful to have a job, you know, at that point. And there weren't as many opportunities for legal professionals as a whole back then compared to what we kind of see today. So the fact that I was able to get in, you know, the front door of a law firm and have an opportunity to
00:03:46
Speaker
experience different ways that the law firm work right so from being a receptionist to working my way up to paralegal and then from there tirelessly reaching for more and not because i was hungry or not because i was bored i just knew that i was driven by ambition and
00:04:05
Speaker
It felt as though there was a little bit more for me to strive.

Storytelling and Mentorship

00:04:08
Speaker
And this is something that Tommy and I have talked a lot about on the podcast, right? Is that storytelling and understanding how do you feel and feed your purpose and that drive, but balance being able to do it in a way that is speaking your love language. And ultimately I just continued to put my head down
00:04:29
Speaker
have great mentors, and really figure out how I can transform the information from different segments to its core function of running legal like a business.

Career Paths in LegalOps

00:04:38
Speaker
And for me that focused on the people, the payments, the technologies that really just improved the business outcomes and delivery of legal services. And then from there, it was just the roller coaster ride from law firm to in-house, in-house to leadership, leadership to chief of staff.
00:04:55
Speaker
I think we're seeing a lot of these similar paths in the industry. They may not be as linear or in the same trajectory, but I'm hoping that my story and Tommy's story as well, right, can be this beacon of hope for people to be active and loud about the past that they took to get in the seats they are today, and then understanding kind of what those core denominators are as we continue to illuminate and shine a light on the path from paralegal to legal operations.

Tommy's Career Transition

00:05:22
Speaker
Tommy, I want to ask you about your path to another title that comes up sort of in concert with paralegal often is like contracts manager or head of contracts or director of contracts. That was a step on the path to you as you built your career towards head of legal ops. Tell us a little bit about how you did it and maybe how running contracts look similar or different to being a paralegal.
00:05:46
Speaker
That's a great point, which is not everyone has the same path to get to legal operations. Some people are out there active attorneys realizing they want to do something more strategic. Some people are out there like Tom was being a paralegal. I was a paralegal for a very short amount of time, but I spent a long time in my career being a contract manager.
00:06:05
Speaker
And how that emerged was working on contracts day in, day out, doing negotiations, working on amendments, trying to make this path of contracting easier. And inside of that, I was like, this is...
00:06:22
Speaker
the volume of contracts that we review. And at the time, I was actually negotiating contracts. So the volume of NDAs, it was actually too much to keep up with. And so my legal operations expertise was born out of survival, right? It was like, how do we do this better?
00:06:41
Speaker
figure out how to systematize the way that the contracts get to us. How do we figure out what we can put back on the business to actually negotiate themselves? What can we teach the business? How can we systematize doing contracts management? And not only was that the people part of what we always talk about in EagleOps, it was also the technology part of it. And so inside of negotiating and wanting to survive and thrive in my role,
00:07:07
Speaker
I really began to see ways that I could leverage technology, ways that I could build out the processes, empower the business, give them information, start to carve out like managing expectations for what they could do, managing exceptions, like what has to come to us, setting up some really solid rules. And all of that inside of it, my GC said to me, you know,
00:07:32
Speaker
As you're building out these contracts and you're building out a technology platform or you're building out better ways for the business to get to market faster, you're doing legal operations. I'm not kidding you. It was like a decade ago. I did not know.
00:07:47
Speaker
what legal operations was.

Skills vs. Mindset in LegalOps

00:07:50
Speaker
And I was like, sure. And then he promoted me into illegal operations role from being a contract manager, because all of the elements of what I was doing really were operational. They were to fit to the business. They were to empower the business and make them get to market faster. It was all operational excellence that I was doing. And I had no idea. And he truly opened my world up in a way that I didn't even know existed at the time. That's incredible.
00:08:17
Speaker
And I want to ask you later about the sort of mentorship aspect of this or the relationship that oftentimes you can develop with your GC or maybe even someone else within the business who's on the leadership side who can help you in this journey. But Tom, I want to ask you first, do you feel like the shift
00:08:39
Speaker
from paralegal to legal ops, not only requires some new skills, but actually requires a mindset shift of sorts. Is that something that you went through? I've waffled back and forth on, is it new skill sets? Is it shifting your mindset? Is it a combination somewhere of both?
00:09:02
Speaker
I think where I land today always evolving so this is I think one of the great parts about both you know us being podcasts right you hosting us hosting talking with different guests you kind of hopefully at the end of the day learn something new and I think yeah years I really have drawn into other people's stories and it's similar to mine and so
00:09:22
Speaker
I think it's understanding what your value is. I say this often, love language, and I'm not specifically talking about these personal skill sets, right? I'm talking about the love language in your career. For me, my father was an accountant. I am a math and science-brained person. I kind of tell Tommy this all the time, right? She's much more creative than I am. I am just dotting I's, crossing T's, analytics, you know, someone call me, you know,
00:09:52
Speaker
Someone call me a little stiff at times, right? But I realized when I had this background as a finance paralegal, right? When I had these skillsets that tapped into the broader math analytics data,
00:10:07
Speaker
connecting A to B to C using points. That's when I turned my perspective into the workplace and thought, okay, instead of it being a liability because I'm not an attorney, because I didn't go to law school, how can I ultimately share my love language, my backstory, and breathe life into that by understanding what were my interests and creating value for my overall firm partners, legal administrators, and then ultimately supporting the GC.
00:10:37
Speaker
And this is where that's where I think it doesn't necessarily require a new skill set if it's something that you are bringing to the table that is running legal like a business.

Importance of Relationship Building

00:10:47
Speaker
Payments, people, process, technology, understanding one of those four core buckets. If you can continue to draw from past experiences, you'll find the way to connect the dots.
00:10:58
Speaker
However, that being said, there are new skill sets that you do have to acquire over time. Uh, and I will say one of them is the relationship part, right? In law firm life, wouldn't say you're necessarily bread and
00:11:12
Speaker
cultivated in a way that understands, as Tommy was saying earlier, the importance of mentorship, the importance of these relationship building. And over the years, I'd probably say relationship building is this 50, 30, 20 rule, where 20% of your time is really spent with people that you should aspire to be, leaders in your industry.
00:11:33
Speaker
Then that 30% is spent within time that are people within your proximity, right? And these where it becomes, you know, your industry specific colleagues or when you're going to networking events or, you know, seminars, or you're trying to do professional advancement, right? It might not be somebody who is specifically in house.
00:11:53
Speaker
legal operations FinTech, right? But maybe a chief of staff who's been doing it for 20 years, who also has great public speaking skills, you know? And then once you do that 30-20 at the beginning for your relationship building over years and over time and kind of where I am right now in my career, you take that and then I hope you mature it, flip it over, and then 50% of your time really is spent paying that forward. And I think
00:12:18
Speaker
That's ultimately where you find the relationship circle of life and how you support your own business partners and those that you may not work with or may have to lean into more as you're developing further relationships as you advance your career.
00:12:32
Speaker
That's really interesting. Another way to ask the skills cut question, I guess, is, is this something that everyone who is a contracts manager or a paralegal should aspire to, right? Like in other words, is the legal ops title or the legal ops role really important? Or are there folks out there who are doing this who might be sort of perfectly happy with where they are and that's okay too?

Exploring Ambition Beyond LegalOps

00:12:56
Speaker
Tommy, I'm curious for your perspective on that.
00:12:59
Speaker
I think it's both. I think there's certainly people out there, and I've had paralegals, I've worked with paralegals, I've talked with paralegals who are matter experts in a certain part of the law. And it's very hard for them to think about shedding a matter expertise, maybe one that they've worked on for a few years, maybe one that they've worked on for their whole career.
00:13:24
Speaker
shedding it to go to a role that may feel more opaque and generalist to them. Like, oh, I'm going to shed being a litigation paralegal where I know exactly what I do, where I can speak to it. I have 10, 20 years of career activity going into interviews. I can ace them. And now you want me to sort of shed that to go
00:13:46
Speaker
Well, just because a litigation paralegal is an incredibly awesome project manager, like you're a project manager, right? You're managing dates, you're managing deliverables, you're, you know, prompting attorneys to produce things by certain days. You are the most supreme project manager and that is nothing if not appropriate for translating out to legal ops.
00:14:08
Speaker
That's a really scary prospect for someone to sort of dip their child in the unknown, right? So first, I think it's a deep, deep, deep introspection into who are you and what do you want out of your career? Now, one thing that I have said to folks when they were on my team is, hey, go out there and
00:14:26
Speaker
I'll nod to legal IO, go out there and do a salary assessment because this is a real thing if you want to think about your ambition and your life and your career. There are real caps on where you're going to get. There's obviously caps everywhere.
00:14:43
Speaker
But if you start to compare what are the caps with the paralegal contract manager roles versus what am I seeing with the caps in a legal ops role, that might be one motivator for folks to go, hmm, you know, I'm going to tip my toe in the pole because it is a, you know, there is a much wider, bigger opportunity there. And then of course, ambition. So I would say to really think about who you are, what your ambition is, whether you're OK with shedding some of the I'm the matter expertise in this practice area of the law versus
00:15:11
Speaker
I'm going into a bigger, more generalist role, like Tom said, running legal like it's a business and taking some of these skills and really transferring them over to this bigger role, which I think has a lot more career opportunity now. And we can even go a few steps deeper, you know, a little bit
00:15:30
Speaker
later in the podcast on where it's actually going beyond legal ops, but it's a question of what is your ambition. It's doing that introspection and really being honest with yourself. If you're not comfortable with it, that's okay. There's other places that you can go inside of the roles where you have that ambition, but if you want bigger, go bigger.
00:15:50
Speaker
Yeah, if you think about going bigger and finding success, I think a lot of it from the conversations that I've had with smart folks like you seems to really be around building trust with a variety of stakeholders and understanding the broader business. Walk us through how one actually does that, Tom. Is it as simple as, you know, you set up meetings with all the product managers and the RevOps folks and
00:16:18
Speaker
Like how does one actually sort of tactically go about building that trust and understanding where the whole business is headed?

Trust and Business Strategy

00:16:25
Speaker
It's the balance between hot and not right. Like I have, I will admit, I have come in all hot and ready to be like, who wants to be my friend? I'm gonna overload you with all of these meetings, all of these different thoughts. I want to, I want to tackle, you know, I want to take it all down in day one and by day two rebuild it and day three go,
00:16:47
Speaker
This is exactly what I love to do, but it's really not how it actually works in the business world, especially if you are in one of these, you know, maybe fortune 500 companies or you're, you know, part of one cog in the overall flow of legal, legal operations and technology innovation.
00:17:05
Speaker
So no, you're not just going to go in on day one and start adding calendar meetings or trying to fill up your first couple of weeks. I will admit I did that and one of my jobs didn't go so well for me. So after learning that wasn't the way to do that, I think I started to lean into this is a marathon, not a sprint, even though more often than not in legal operations and in-house roles, it feels like a sprint even on day one.
00:17:33
Speaker
So shifting from that traditional, I got to meet everybody. I got to take care of everything on day one, which sometimes are, you know, habits that have been brought on from paralegal or other roles at law firms, right? Because they want that instant response, want that handholding. They want more of that administrative expertise, shifting it to legal operations, shifting it to a strategy versus subject matter expertise.
00:18:00
Speaker
you're going to lean into your GC. You're going to then ask the GC, who are the people that I need to understand are the important VIP business stakeholders? And from there, then slowly dripping out that you are new, that you're trying to understand where they are, and just really listen a lot. And at some point, depending upon what the business is,
00:18:24
Speaker
That's when you start to see legal operations come in, and you're seeing them take the reins, and really not just be that trusted right hand of the general counsel, but the other business stakeholders at a leadership level. But it's not done overnight, and it's not done trying to just go ahead and say, I'm going to take on all of HR, all of finance, all of technology, all of infosec, all of privacy. If you do that, you're definitely going to fail right out the gate.
00:18:50
Speaker
I love hearing about experiences where things might not have gone quite as well in one job as you would have hoped, and then you fixed it in the next one. I try to tease those stories out on this podcast. I can't always do it, so thank you for sharing that, Tom.
00:19:09
Speaker
I think another piece here is, as you become sort of the head of legal ops and start to build a team out under you, there's a management question as well,

Management Skills through Mentorship

00:19:17
Speaker
right? You're not just trying to understand, okay, how do I find the best person to manage our technology? And I've done that before myself, so I can do some coaching, right? You're actually thinking about sort of, how do you manage this whole team? How do you motivate folks? How do you provide them with growth opportunities? Tommy, talk us through maybe how you've picked up
00:19:38
Speaker
some of those management skills over time and cultivated yourself as a manager. I cannot overstate enough the value of coaches, mentorships, community, colleagues. There can be colleagues that you admire and aspire to be. They're not on your team. There's a woman at Cedar who gives the most amazing presentations at all hands. I go bananas when she's up there.
00:20:08
Speaker
She's I believe on our product team and I'm just like in awe of what she does and in our all hands recently.
00:20:16
Speaker
I'm going wild, like, you know, giving her her flowers. I'm like, please hold a class on giving presentations because you're so great. You integrate storytelling so beautifully. And so what I'm saying is go find the people that you aspire to around the business, around your community, wherever they are. But throughout my, you know, throughout my life, I've been able to take what I wanted from certain leaders, but also know what to put down and not take from them. Right. So I've had.
00:20:44
Speaker
You know, I've myself and others have had folks who their managers were micromanagers and, and, you know, the, the, the age old question during a, during an interview, like what type of leader are you really early in my career, I would answer it.
00:20:59
Speaker
you know, conversely, and I would say, well, I'm not a micromanager. Like I know that, right? And then, you know, because I didn't sort of, it was early and I was still learning like what kind of leader I was. And the later I learned I was more of a servant leader. Like I was more of allowing someone to be the, the person who is running the show and they're coming to me and we're collaborating. And now it's more of like a real collaboration, right? It's really,
00:21:25
Speaker
I want to find the folks that are far, far, far more talented and smarter than me to be on my team. Like I don't actually even want the show to be about me. I want it to be about like whose career grew under, you know, under me into, you know, an explosion of flowers and ambition. Like I want to find those folks. There's no, there's no ego in it. It's all about like,
00:21:52
Speaker
us lifting each other. And so I would certainly say that I'm looking for the talent, looking for people that have that ambition. But even as they just mentioned with finding a contract manager or a paralegal and someone who is not interested in growing that way,
00:22:07
Speaker
that's okay too, like what are you interested in? So even in my own reviews, I've now come to a place in my career where I'm comfortable enough, but this is really hard and uncomfortable when you're early in your career, but now I'm at a place where it's like, we're also talking about what I want to do in my career and where does that look like in five, 10 years? And what do I do today that gets me in that roadmap? So some of it is knowing where you want to go and what you want to do.
00:22:33
Speaker
It's managing your your manager because you're managing your career. And so I really try, especially with those folks that are that are new or
00:22:42
Speaker
who are a couple of years into their career, be thinking five, 10 years down the road. Where do you want to go? What do I do with you here today that gets you there, that puts you in the right direction of going where you want to go, forcing someone to look introspectively, forcing them to want to take control of their own roadmap. But really, it's collaboration. And it is definitely about me not being the smartest person in the room.
00:23:07
Speaker
Like I really want to stand back, stand down and give people the opportunities. Some will be great. They'll hit it out of the park. Some will be a stretch. And that's great too. Some, some will all fail together, but letting people be comfy and confident enough to know that the failures are safe.
00:23:28
Speaker
We're all doing this. We're all figuring some of it out. You know, sort of checking the ego. That is really what I hope folks who have been with me and under me have learned and have seen. And that's the example that I want. And I've learned it from coaches, from mentors, from
00:23:45
Speaker
from friends, people in the community, it's really all about us just growing together. A follow-up for you there, and I also really want to hear Tom's thoughts on this too. As you take on ahead of legal ops role, the ability to build out and manage a team is super important.
00:24:06
Speaker
But another observation would be the ability to manage up to your GC is just as important. How do you develop the right relationship, a trusting relationship with your GC? Tommy, I want you to take this first and then I really want to hear Tom's views here too.

Building Relationships with GCs

00:24:23
Speaker
Absolutely. I think the answer is in the same way that you develop most relationships. It's about being honest. It's about being vulnerable.
00:24:33
Speaker
that is a really uncomfortable place for folks, right? Like that's a really uncomfortable place for folks to really be honest and vulnerable. Say, I don't know what I, I don't know. I'm going to go figure this out. Seeing if the vulnerability goes both ways. I've learned to have a bit of a keen eye during interviews. And so some of it can be
00:24:56
Speaker
not even getting into a role where that relationship is not going to hit. It is a relationship at the end of the day. Hopefully you can start to figure out
00:25:11
Speaker
Are we vibing together? Are we able to communicate? Can we start to figure out how to anticipate each other's needs? That's really hard to do in an interview, right? When you have 30 minutes, it's really hard to do. You're trying to do it with the people who might be your colleagues, but you can start to plant the seeds there. And I've been able to pretty successfully figure out by looking at it like it is a relationship. It is going to be built on trust. It is going to be built on a shared vision.
00:25:36
Speaker
and understanding like, are we moving in the same direction or are we not? And all of that is communication. It's like trying to get at the heart of what we're trying to achieve here. What do we want this team to look like? What do we want our wins to look like? Like, who are we as a team? And a lot of the kumbaya stuff that goes into doing on-sites and getting to know each other better. But again, as Tom said before,
00:26:00
Speaker
We're people. People are at the center of all this, right? Like we're at the center of the universe. We're working hard alongside these people. So it's about building the relationships with people. You can figure out who you're going to vibe with and not. When I was interviewing at Cedar,
00:26:16
Speaker
Vanessa and I, who was a guest right here on this podcast, she and I talked for several weeks. We would talk on the phone, we would talk about the office, we would talk about culture. We were vetting each other from a personal perspective. Like, can I work alongside with this person? Like, can we vibe basically? Like, I know it's so silly.
00:26:39
Speaker
Like, can we vibe with each other? And I really, after the phone calls and talking and through the negotiation about the role, like I really began to realize like, this is a person who I can work with, who I can be in the trenches with, who I can talk to, who I can tell I succeeded or failed or what success, you know, build out what success and failure looks like together.
00:27:00
Speaker
So at the end of the day, it's as hard and as simple as it is a relationship and vet it like it is one. And do you want to win alongside this person? Are they going to have your back? Are they going to speak highly of you in rooms you are not in? Like is this your person? And then go out and find them.
00:27:16
Speaker
I think that's, and then Tom, I really want to hear your view here too. I think that's so underestimated though. After I took the job at Spotdraft and even still people will ask me, you know, what are you doing? Why do you like it? And one of the things that I would say, you know, among like, you know, three or four others was I really liked Shashank. And right, having a CEO who I admired, wanted to work with, thought that I could learn from
00:27:45
Speaker
was going to have a very honest relationship with was very important to me. And I think sometimes people look at you and like, yeah, but like, why would that be the thing that convinced you to work there as opposed to, you know, what's the scope of the role? What's the salary? What's the promotion schedule going to look like? And, and to me, it was more about picking the purse, like almost like picking the right horse to bet on, right? More than anything else. Like if I work with him, good things will happen.
00:28:13
Speaker
cannot be understated. Right, exactly. So I think that you've hit on something that people really underestimate as a part of the interview process. If they view taking the job often as something that's very transactional, they might focus on other things as opposed to who they're going to be working with.
00:28:33
Speaker
this is exactly how it is. While you both are giving your little flowers out and loves right to those that you work for. It truly was the exact same journey for me. Now I will say that along this journey, right, I think one of my strongest skill sets and that allows me to be both authentically Tom and vulnerable while holding the power of leadership.
00:28:55
Speaker
mentorship has always been rooted in this people-centric segment right within your career. And this can be through mentorship opportunities,
00:29:05
Speaker
learning to get up when you fall down, right? A lot of these like different skillsets that you learn over time, the disappointments, the highs, the lows, right? The getting passed over for promotions and then understanding what you need, right? To actually make that go the second time. And it really sticks out to me that, yeah, when I, in my current role at LegalIO here, it's, yeah, I understood who Peter was. I knew what LegalIO did, right? I used them. I was, you know,
00:29:34
Speaker
one of their largest clients when I was at Credit Karma and it was because I loved the way that ALSPs and those models allowed you to shift from outside counsel spend to human resources and that was just something I really thought is needed a little bit more as we're trying to get over the doing more with less mentality that is so gross right now for the in-house teams.
00:29:57
Speaker
And it was finally when I had met with Peter and he was just encouraging me to really kind of talk about what I have done over time. And so as I was getting ready for these interviews and I was like, all right, let me go ahead and tell him my story, right? I remembered something that a mentor had told me, which is that
00:30:14
Speaker
You know, people don't care about how much you know until they know how much you care. And this understanding who you are, your branding, your work relationship, you know, your love language, right? All of those is not about just talking about yourself, right? It's about making sure other people know who you want to be and who you are. And I think that's when I kind of took these times to make some changes in my life and remember that that center of excellence
00:30:44
Speaker
there's always something that's been in the community for me. And so I worked really, really hard over the last few years and some of the days were really long, right? But I was finding my purpose in my drive and it was an insatiable thirst to learn. And that's really kind of what allowed me to get into this wonderful role that I'm now in at Legal.io.
00:31:01
Speaker
I don't want to make you say the same thing again, Tom, but I do have a question here about the working relationship with the GC.

Balancing GC Input and New Processes

00:31:08
Speaker
And I suppose it's not that different than the working relationship with any other executive, but to what extent are you taking cues from them on the broader strategy versus you helping them set that because you have subject matter expertise in a lot of areas where even though you're in legal, frankly, like a lot of general counsels probably, they're not going to know that much
00:31:31
Speaker
about eDiscovery unless they have like maybe like a super deep litigation background or if they came out of the VC world or right VC corporate world. So to what extent are you sort of taking cues from them versus figuring out the right way to tell them hey these are actually the processes and programs that we need to invest in and build out.
00:31:51
Speaker
It's, it's been the, it's, it's the one thing I have focused the most on in the last number of years. And it has served me well, right. Whether it is reporting directly to a GC, whether reporting now directly to a CEO one day, you know, being in charge of hiring the first GC at our company, right. Since I handle all of our legal currently right now, it's about understanding that, you know, we've said for decades, right, that attorneys should focus more on legal work and.
00:32:16
Speaker
making sure they use their law school degrees and all the things that they really went to have that awesome delivery of legal services. But the pathway for legal operations has opened up the door to be that trusted business partner. And when you're showing those data driven approaches and
00:32:32
Speaker
Leaning into the experiences from your non-traditional pathways, that's when you have the opportunity to really shine in front of your GC. So for me, it was, okay, maybe I don't need to then focus on hiring somebody right to show the value of having billing guidelines that save money, right?
00:32:49
Speaker
But what I do need to do is I need to show how legal is moving past being a cost center and a true business partner that creates value. And that was the love language right of the GC because they're at that strategic level. And so when I think of the relationships that you build with GCs, CLOs, executives at any company in-house or
00:33:09
Speaker
as an ALSP legal vendor, it really does come down to how can you understand what they need? And then how can you understand what your expertise is? And then like a cute little Venn diagram, where's that center of excellence, right? Where is that place that you can understand that focusing on your skill sets and your strengths and creating a space where you can thrive means listening,
00:33:32
Speaker
means understanding the business and ultimately leaning into each other during those periods of vulnerability. As you said earlier, they may not know a discovery, right? They may not know about specifically how the accrual process works. They may not want to be bothered, right? With CLM implementations and mapping data sets, right? But what they do want to understand is how is this journey going along for you? How is it ultimately going to create trust within the legal team?
00:33:57
Speaker
How can we be the front door that says yes? And when you start to work together using those different skillsets, that's when the magic really does happen. And that's truly how I came to become a part of a legal operations team originally was being so close to the business, knowing what all their frustrations and pain points were with a legal team. It was truly like a, like a department of.
00:34:22
Speaker
Like we were, we were, we literally were the back office, like on the floor, there was a back office and that was legal team. And it was, it was, there was no integration. There was no.
00:34:33
Speaker
you know, collaboration, it just was like, I will drop this contract into this black hole and maybe someday we'll come back again one day. Who knows? We'll see, right? Let's, let's put our numbers on red. And like, so it was bringing it all together, but it was because I was so close to the business. I was so steeped in what they were doing. I was going to their meetings and I'm coming back to my GC going, here's what the strategy is. Here's what they are doing. Here's what they're hoping to achieve. Here are what their objectives are.
00:35:02
Speaker
That brought us closer together. And now I work for organizations where a lot of the executive teams really realize how integral a CLO or a GC is. So they're there, they're building out the strategy for the business. And then, you know, having been a part of strategies and having been, you know, a bridge builder between the two different worlds, if you will, it's sitting there and going, okay, how do we now, how do I sit with my CLO or GC?
00:35:31
Speaker
How do I execute on what the business strategy is? How do I ensure that the legal expertise is really supporting what the bigger visions are? But you can be that strategic leader and you can have the seat at the table because of how steep you are inside of what the business is doing.
00:35:47
Speaker
And that's the opportunity. Like that is the opportunity to holistically impact your business. Okay. Seat at the table. That's an important phrase. And I think you have an opinion on this, Tommy, or your opinion may depend on sort of the business, but how important is it for you to be on your GC's leadership team as the head of legal ops?

Advocating for Leadership Roles

00:36:09
Speaker
I think it's very important. And so I appreciate that that may not always be an opportunity. And so I certainly don't want anyone to feel like, Oh, I'm not winning if I don't have a seat at that table. But if you can advocate for it, and if you can get the seat at that table on the leadership team of the office of the GC of the CLO office,
00:36:27
Speaker
And I think a lot of CLOs and GCs are trending towards actually putting their legal operations person at the table because they realize when they're sitting in their leadership team meetings with all the leaders from all the practice areas, having the centralized person who can help to execute on what each of their different plans are, removing all the friction points for each of those different practice areas, that's the win, right? So they're realizing and they're giving you that seat at the table.
00:36:53
Speaker
And I think if you are going to be in the role where you are that strategic person, where you're acting like a chief of staff, that person has to have a seat at the table. Otherwise, not only are they going to have a really hard time getting their work done, getting buy-in from other leaders, but let's face it. Politically, there is the setting the tone of what you want the vision of your department to be.
00:37:18
Speaker
And having someone who's going out and attempting to execute on that, when they see that the leaders of that team have bought into that, everyone else in the department is going to go, I'm going to help this person. I'm going to take their meetings. I'm going to work towards a shared vision. If it's questionable or opaque or people are like, do I really?
00:37:40
Speaker
do this? Is this really a strategy payoff? They may not be so bought in. So it is a signal. It's a signal that, no, no, this is what we are doing. And I have an expectation as a leader. I have an expectation as a leadership team
00:37:57
Speaker
And when you're getting the buy-in from that team, everyone's coming together and they're collaborating. So can you do your job without it? Yes. And I don't want anyone to feel like, oh, I'm not going to be a success because they don't have a seat at that table. You can, you will advocate for it, do what you have to do. But when you get the seat at the table,
00:38:17
Speaker
people start to really see what is happening. There's not several layers of translation of what you're doing. I'm here. I'm presenting to you. I'm showing you the wins. I'm showing you the impact I'm having. And it is such a shortcut that helps your career and helps the team that I think it is very, very, very important to advocate for and to have.
00:38:38
Speaker
It might create the environment or the opportunities that allow you to think about what's next, give you the exposure to think about what's next. Tom, you've gone on to not only do legal ops, but also lead community for legal.io.
00:38:55
Speaker
Tell us about how that came about. Was that something that was part of your plan? Did it just happen organically because of all the relationships you had in the industry? Tell us about how you managed to take on something that frankly is more on the business side as opposed to the legal side.
00:39:14
Speaker
I think the answer is yes, yes, and yes. My natural instinct, the one that I want to say out loud was, no, it wasn't part of the plan. But then as I'm looking back, as I'm thinking about my journey, it may not have been the plan, but it absolutely was the highway I was always going down, whether or not I knew it was a marked or unmarked road.
00:39:33
Speaker
And for me, how it came about was I just, I was at a point in my career and Tommy was a very, very close, confident during this time. Um, and much like the community, right? As we lean into, what are your struggles? What are you seeing? Have you been in this before? And I had a lot of people that said, um, actually being included, right? Of, Hey, how do you ultimately.
00:39:57
Speaker
Level up your career when you know that you are doing the things you need to do. You are hitting your metrics, but you are still hungry. You want to grow for more. And we are seeing a lot of this in the legal ops and the legal tech community right now.
00:40:12
Speaker
It's these individuals who are transitioning from different segments, but ultimately still doing legal ops or legal technology as a core function, but still helping with growing the business in whatever needs legal or business can actually move it forward.
00:40:29
Speaker
And so the one piece of advice I really want everyone to hear is when you're determining where you are at in your career, make sure that you understand your business acumen and professional emotional intelligence, because that is ultimately the key to success.

Tom Stevenson’s Role Transition

00:40:43
Speaker
It's about building these connections and making a real impact and.
00:40:47
Speaker
I found that I was at a space in my career where I wanted to actually create more space and looking back, right, I went from receptionist to paralegal to head of legal ops and a de facto chief of staff role. And now my title of vice president of community and legal operations at Legal I.O.
00:41:07
Speaker
really is this amalgamation, right? When I needed to listen to myself and not just say it out loud, but lean into my own professional network.
00:41:17
Speaker
that there are multiple paths to success. And when I realized I was data driven, right, math and science, I started to get the creativity through the podcast. It helped with my leadership skills and my speaking skills. All of those, when I mixed it up into a bowl, I actually reached out to legal IO and I said, I think I'm ready for a new career. Can you help me? You know, let me know about jobs. Keep me on, you know, your short list of things.
00:41:42
Speaker
These are something that, you know, I'm interested in doing. And much like life isn't really following a set script, they a hundred percent just flipped it around and turned it into something different. And I was a little bit imposterous in them, right? I was thinking, Oh my gosh, can I leave a fortune 500 company where I have a
00:42:01
Speaker
team under me and, you know, I'm at these leadership meetings and I'm doing things in my career that's much more on the chief of staff role. And then flip that script into a startup environment in which I am heading up legal and legal operations while doing community while at the same time, as you know, you know, as both of you know, being both for, you know, um, early, you know, staged companies, right? Who are also in their own, you know, uh, journey.
00:42:29
Speaker
Yeah. How are you doing it? All right. Sometimes you need to be pulled into both getting that MSA and doing the accruals and being able to attend a dinner while like hosting somebody on a podcast. Right. And it's where you find that advocacy, that passion. And that's where I ultimately found, you know, my own voice in my route. And I do hope that, you know, for anyone that's listening, that they do take those opportunities that are given to them in their career, because if
00:42:57
Speaker
they are able to step outside of what they think a traditional path looks like and understand who they are and where their passion is and where they create value. Then I don't think that there's ever a career path that ends for people. You just transition that and think differently to be able to gain new skill sets.
00:43:14
Speaker
Tommy, Tom referenced some of this. I think there's a big conversation happening in LegalOps right now about how transitioning to a chief of staff to a GC or COO role, or even to something that's more of a general operations role like COO, sort of like how our COO at Spotdraft came from running LegalOps at Coinbase and before that at what was Facebook, now Meta.

Expanding Career Pathways

00:43:43
Speaker
What's your view on that trend? Is that also something that you might want to do someday? I'm going to answer you, but I'm also going to say when Tom was talking about having a dinner and doing a podcast and doing accruals and doing an MSA, my, my mind made like an AI photo of all those things happening at the same time where he's at the dinner, he's got a mic in his hand, one hand's doing accruals, one's doing the MSA.
00:44:13
Speaker
You're just doing it all over there. Is an octopus your spirit animal, Tom? I have eight tentacles and they're just trying to figure out where to go. I think this is what is so incredible about legal operations. This is why I said earlier, if you're a paralegal or a contract manager, you have to dig into what
00:44:37
Speaker
your ambition is and what you want to go. I remember so clearly it's like a crystal memory in my head when I was a paralegal and I was a paralegal at a record company and it couldn't be more fun and the guy who was like my work, Bessie, who I worked on literally sat right next to him day after day, he's now the GC for huge. I remember he was applying to law school and I was thinking to myself like,
00:45:01
Speaker
You know, I am just never going to wake up one day and be an attorney. I'm also never going to wake up one day and want to be an attorney. So what, what do I do? And it was such a conundrum because I'm not going to date myself, but it was a hundred years ago. And being that it was so long ago, there wasn't a legal operations role. And in fact, when I got the call from HBO to come be a contract manager,
00:45:27
Speaker
That was the first time my mind had ever realized like, oh, that's the leap. And that's how early in that inception, like that even contract managers were coming into their own, right? And again, it was like 100 years ago. So it was this really hard struggle I had, which was what do I do? Like, what do I do with my career? Because I don't want to go to law school, frankly.
00:45:52
Speaker
And I struggled through it a little, but like through it, right? Like I went through it and I started to more lean into what do I like and what gets me jazzed and what's interesting

Breaking Career Ceilings

00:46:03
Speaker
and how do I sort of deliver my work with integrity and in kind of always being honest with myself and looking at the things that I like and matching what I was really good at with things that I really enjoyed.
00:46:13
Speaker
There came the evolution and sort of the revolution. And now I find myself inside of a function, a place, like a job that I love. But also now that all of these really cool and smart and ambitious legal ops people have started to set the blaze literally on fire, like they have trailblazed it.
00:46:38
Speaker
And you just mentioned Akshay. So now we have someone who was in strategic legal operations role who realized, and there were many that came before him. And I don't want to sort of forget about them. Like even Tom on the community side, Mary came first. Like, you know, there's so many people who blaze the trail, but it was setting the stage for there being
00:46:59
Speaker
operational ways that we work that translate far outside and far broader than what we're doing here just inside of the legal department. If you can run your legal department like a business, which is a big Connie saying, you run it like a business, guess what? That application goes wider. It goes to running a business like a business, right? You're managing finances, you're managing
00:47:27
Speaker
all the cross-functional teams that you work with, you're managing how, you know, contracting, which is probably like 80% of any, you know, good business, whether it's sales, whether it's doing M&A, like whatever you're doing, you're, you're putting some legalese around it.
00:47:42
Speaker
So you're taking all these transferable skills. So I would say, if you asked me this question three years ago, I would go, oh, the evolution naturally is into a chief of staff role. Like it's being the right hand to the person who's at the helm. And that's as far as we get. And then all of a sudden, everything shakes up. And it's like, that's not actually as far as we get. Whoa, someone blew the ceiling off of this. A couple of someone's blew the ceiling off of this.
00:48:08
Speaker
wow now we go even wider now we can actually and I promise you I'm not joking in a review I just had with my boss when as I just said like that's a part of you know my talking points in reviews which is where do I see myself where do I want to go it's making sure we're both aligned on what my career is we're both aligned on what you know she wants for the business for the team like what is my contribution there but also what's her contribution back to mentoring me into what my bigger objectives are
00:48:37
Speaker
It was, hey, I can certainly transfer these operational skills bigger, wider. What do they look like? What do they look like inside of this organization? What do they look like on the big stage? And so really thinking about the reality that we could take these operational skills and bring them properly to a business, that might be the ceiling someone's breaking through in five years, right? But that's the one that I think we're starting to see play out now, which is incredible. And it really speaks to
00:49:05
Speaker
what strategic leaders we are in legal ops. Well, as we start to wrap up, we're actually not done because we're going to continue the conversation at clock where I am super excited to see both of you very soon.

Upcoming Panels at CLOCK

00:49:20
Speaker
And I wanted to give each of you a chance to sort of talk about your panel that you're doing at clock and also where people can find you. Because I'm sure after this episode, a bunch of folks are going to be thinking,
00:49:33
Speaker
How can I go and share half a coffee with Tom or Tommy at clock? You're going to be mobbed. Tom, we'll take our coffees together, right? Yes. We'll do coffee. You and I drink out of the same coffee, and someone else can have that.
00:49:53
Speaker
Yeah, so let me go first. So I'm really excited. I'm moderating a panel with Janine Dixon from META and Andrew Mendenhall from Zoom. It is on Wednesday, May 8th from 11.40 to 12.10 p.m. And the session is titled Building Bridges
00:50:11
Speaker
personal branding for career progression and in true dad joke form, right? I'm going to be interviewing both of them kind of TED talk style on the stage. And we're going to be talking about this, this notion of how do you build your career much like you are building a bridge, right?
00:50:32
Speaker
And kind of as though what Tommy and I talked about earlier today, right as we're thinking about our professional paths, if you make them truly yours, it's this mix of your identity, your past experiences, your skills, but then also there's that personal branding side. And so we're really going to dive into the session talking about how, how do you build this?
00:50:53
Speaker
professional and personal brand, right? How can it reflect the real you and show what you can bring the table, but now here's where they come, right? But it's going to actually talk about bridging the gap, right? Between uncertainties and those big opportunities that are waiting on the other side of the bridge. And as we continue to think of our careers as walking across the bridge, step by step,
00:51:15
Speaker
We also have to remember the foundation of how a bridge is built, right? And it doesn't just come from, you know, the materials or the vision or the purpose, right? But it's really the hard work of the people that ultimately and collectively get that bridge built up and make sure that is structure is solid, solid to like let a boat run into it, but solid enough that like it happens, right? So we're really going to be talking about and hearing stories, both from Janine and Angela, how they have shaped their own brand, how they've
00:51:45
Speaker
been the masterminds behind the design and the bridge itself. And then really how we've all three of us over time in this wild world of legal operations, legal technology and chief of staff, right, have been able to link our goals, not just to the person that we're becoming, but quite frankly, the type of career that we want to build and inspire others to follow along as we continue to open more doors. So really, really excited for this awesome session. Yeah, and then if anyone wants to,
00:52:15
Speaker
connect with me. You can find me on LinkedIn, Tom Stevenson, VP of Community and Legal Operations at Legal.io. And you'll be seeing my flashy blazers, my sparkly shoes, anything else, probably hanging on the side of Tommy for most of the conference.
00:52:30
Speaker
He's going to be attached to me. So you, uh, this wonderful audience at the abstract can reach me at linkedin.com slash Tommy and oh boy, where to begin with CGI 2024. So I'm super proud to be doing the foundations of legal op.
00:52:47
Speaker
the Foundations of LegalOps 101 workshop. It's a half a day. It's the Monday before the conference begins. And I love ushering in this new class of legal operations professional. This is something that's near and dear to my heart. So I'm so, so happy to be doing the 101. And the next day, there's a networking breakfast with some folks that are new to legal operations. And it'll be their first time going to CGI. So excited to be at that. Then I'm doing a solutions lab with Walter's Clor about legal ticketing.
00:53:17
Speaker
And my panel with the beloved Adam Becker of Cockroach Labs, and he's also sitting on the board of clock, Tereen Collins from Panasonic, Lori David Henrich. I cannot wait for our panel, which is called The Invisible Woman Was Wrong. Visibility is your superpower, which is all about utilizing
00:53:41
Speaker
your wins and your brand and all that you're doing in your day job to, you know, bring success to your role. It's about sort of leveling up the way that you perform and the way that you can sort of harness the power of your performance to level up your career. I think it's going to be a great chat. And last, but certainly not least, doing the Solution Lab with Spot Draft alongside Brenda Perez, Akshay Doshi, and of course Akshay from
00:54:11
Speaker
Spot Trap, which I am just so thrilled about doing. So thank you for that opportunity. Yes. And we are very excited also that this was sort of a sign to us, but that we happen to be the sponsor of both of your panels as well. So once again, this is just all the good juju you're throwing out into the world. That's coming back. Clock new. Clock new. They said, hey, you've got friends on these panels.
00:54:40
Speaker
I was super proud to see that we had the spot draft logo. Um, it's great. It's great because we love chatting with you. We love talking with all of you. So this is wonderful. Uh, well, Tom and Tommy, thank you so much for joining this episode of the abstract and creating this with me. This was a lot of fun. We had a great time. What do you think, Tom?
00:55:04
Speaker
Oh, so great. Cannot wait to do this again in a couple of weeks in person. And thank you so much. Thank you and see you at clock and to all of our listeners. Thanks so much for tuning in. Hope to see you at clock as well.