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Defining Ethical Use & Dealing with Law Enforcement: Mark Kahn, Partner and Head of Consumer at Protégé Search
92 Plays1 year ago
How does legal determine what is acceptable user behavior? How do lawyers weigh the needs of users and concerns from law enforcement to arrive at the best guidelines for responsibly protecting our data?
Join Protégé Search Partner and Head of Consumer Mark Kahn as he shares his experiences on the front lines of privacy protection in his roles as VP of Ethical Use at Twilio and Deputy General Counsel at Whatsapp. In a time of major international crises, how do tech companies navigate the difficult questions about ethics, acceptable use, and fairness?
We’ll hear about his journey from the Oakland A’s, to the legal teams of tech’s biggest players, to his newest career guiding others on their professional career paths as an executive recruiter. We’ll also get some tips about recognizing when you’re in the right role, how to make a leap to the executive suite, and when to step back from a stressful position.
Read detailed summary: https://www.spotdraft.com/podcast/episode-18
Topics:
Introduction: 00:05
Starting your career in product with your dream organization: 1:22
Working your way up the corporate food chain to Whatsapp: 6:22
How Whatsapp differed from his expectations: 12:39
Knowing when to step back from a stressful role and leave: 18:27
Taking time off and negotiating a role at Segment: 24:13
Working with an executive coach: 29:13
The Segment/Twilio acquisition and carving out a new role for “VP of Ethical Use:” 30:13
Stepping away from law into exec recruiter role: 38:15
Demystifying the job seeking experience: 40:29
“Designing Your Life” and advice to his younger self: 43:23
Connect with us:
Mark Kahn: https://www.linkedin.com/in/markkahn2/
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
Introduction & Guest Background
00:00:05
Speaker
When I asked today's guest whether he'd be open to talking about some of the most challenging moments in his career, from facing ethical dilemmas, to navigating failure, to burning out, his answer was actually a resounding yes. Today's episode is a special one. I'm Tyler Finn, and today I have the pleasure of speaking with Mark Khan.
00:00:25
Speaker
is a partner at Proteze Church. Marx had an incredible career, from working for a baseball team, to being legal counsel for tech companies like Yahoo, Evernote, WhatsApp, and Twilio, and now he's an executive recruiter helping companies hire the right diverse exec level talent.
00:00:42
Speaker
legal or otherwise. A common theme in his career trajectory seems to be change and perseverance.
Career Beginnings: From Computer Science to Law
00:00:50
Speaker
And for this episode, we're going to explore three core areas or moments of his life through this lens. Mark, we're really happy to have you here with us today. Thanks for agreeing to candidly discuss some difficult times in your career. Welcome to the podcast.
00:01:05
Speaker
Thanks, Tyler. Great to be here. Thank you for having me on and let me talk about, I guess, my favorite topic, which is me. I don't know. Anyways, that sounds a little weird, but whatever. It's good to be here and happy to go in any direction you want to take this conversation.
00:01:22
Speaker
Before we start talking about WhatsApp and Segment and Twilio and all the places that you ended up working, Mark, I'd like to go back to the very beginning of your career when you were deciding to become a lawyer. Tell us a little bit about the why, what motivated you, and how you actually went about becoming a lawyer.
00:01:41
Speaker
I graduated college in 1992 had a degree in computer science. Wasn't really into hardcore programming like there were people if my graduating class who would like go to the mainframe computer essentially and these high powered workstations and like just code for fun all night all weekend. That was not me.
00:01:59
Speaker
And so I decided I went and got a job that we use my computer science, but was not sort of hardcore. So I end up working for this company that was sort of like Ticketmaster was an event ticketing space. But this is what before internet ticketing or anything like that, you would go to music stores to buy your concert tickets and things like that.
00:02:18
Speaker
The Oakland A's ended up becoming a client of ours. They were looking for somebody to help them, you know, somebody who really knew the system inside and out to kind of help them run their season ticketing and all that. So I joined the Oakland A's to run the ticket operations. The president of the Oakland A's at the time was a guy named Sandy Alderson. Sandy was sort of an early mentor of mine. I remember a funny incident where he came into my office when the A's were talking about reacquiring Jose Canseco and was like,
00:02:45
Speaker
We're thinking of bringing Conseco back. What would that do to ticket sales? I was like, oh, God. How did I get here? I was like, I don't know, probably like 50,000 over the course of the season, something like 50,000 tickets, maybe. I don't know. He's sort of a little washed at this point, it felt like, but he's still a big draw. I think it would help. Anyways, they ended up reacquiring Conseco. Anyway, Sandy was a mentor of mine, and he's a very smart, Harvard-trained lawyer.
00:03:13
Speaker
This is now sort of the mid 90s, 95, 96. The days were not very good at that time. There had been an ownership change. I was starting to think about, okay, is this sort of my dream to work in baseball?
Legal Career Evolution
00:03:25
Speaker
But what I found was, is like, it was sort of like any other job. And it was, and actually one of the real downsides of it was, I was like, not enjoying going to baseball games. Not really bothering me.
00:03:36
Speaker
It's like going to, going to the office. Something like that. And so I started to think about, well, I never really expected to go back to school, but I started thinking about like, uh, now you're starting to see some activity in tech. And I was like, well, what if I took this computer science degree and married it with a law degree? I think it would be really fun. And I think it could really add a lot of value to tech companies. And I, you know, sort of went in how, like ultimately the goal was to go be a tech company lawyer, whatever that
00:04:05
Speaker
I didn't know what that meant at the time. I just figured, hey, I understand technology. I versed in it. I figured there was something to be done there, but I wasn't sure exactly why. And so I ended up applying to law school. And yeah, so 97 and then graduated in 2000.
00:04:24
Speaker
And that played out for quite a while, right? You ended up making it in-house and had some success. I started nosing around, repositioned myself as a litigator. Even though I wanted to do tech trans, but I'm like, look, there's no tech trans market right now. And I'm like, oh, I'm a clerk in a district court, federal district court in Atlanta. We wanted to come back out here. That was always the plan. I'm a litigator. Yay.
00:04:50
Speaker
I ended up going to this boutique litigation firm in San Francisco called Roger Joseph O'Donnell. He's all of about 30 attorneys. Did a commercial litigation, government contracts, professional liability. We did a lot of legal malpractice stuff. A lot of ex-big firm folks. A lot of folks who've been at the old Pettit Martin firm, which has long since gone.
00:05:08
Speaker
And it was great, it was great. I mean, I really enjoyed being at that firm. It was good people. I'm still friends with a number of folks, Allen Joseph, who was the Joseph and Rogers Joseph. He passed away a number of years ago, but he and I were very, became very close. He came to my, like actually the last place he was before he passed away of pancreatic cancer, the last public event he was at was my son's bar mitzvah. So it was a good place with good people and I enjoyed it. But I kind of knew that not really what I wanted to be doing,
00:05:38
Speaker
And I got a reach out about from a headhunter or recruiter about going to a software company to basically go support their government contracts business. So I was doing a lot of government contract work with more of a DC practice. And so this was because the company was business object. So they were dual headquartered in San Jose and Paris. And so they were looking for somebody to support the government business.
00:06:00
Speaker
ideally out here. And so I was a little bit of a unicorn in that respect. There weren't a lot of people around my graduation time out in California who knew government contracts. And so that's what I did.
WhatsApp Journey
00:06:15
Speaker
I joined Business Objects to support their government business and then also did a lot of commercial licensing transactions there.
00:06:22
Speaker
And you worked your way sort of up the, up the in-house food chain from, you know, sort of one successive role to another. Tell us a little bit about that journey to, I think what's going to be our first sort of break or topic, which is the time at WhatsApp. Yeah. So the funny thing is about that business optics job, great company didn't really like the job.
00:06:42
Speaker
at all. Like that was like rinse and repeat, like how many times can I negotiate an indemnity? How many and I wasn't, I didn't feel like I was very good at it. It was really my first bout with imposter syndrome because I had been raised as a litigator. I had never had that sort of transactional training. And so the litigation background was helpful, but it's still like I, to this day, I didn't feel like I've never been super, I don't think I'm a very, a very good contract drafter. I think I have other lawyer skills, which are much better and more advanced than that.
00:07:10
Speaker
I was actually on the verge of going back to my law firm because I was like, I was not happy. Then this event happened. It was sort of happenstance. And I've had this happen a few times where the general counsel who had come from IBM, he had been at the company for all of six months comes into my office and he's like, or calls me down to his office more accurately and says, Hey, I need to, I need you to help out on a project. Like, okay. You can't talk with anybody about it.
00:07:34
Speaker
OK, so he's like, you have you have access to all the contracts that the company has, right? I'm like, yeah, because he knew I was working on this contract management. We were looking at contract management options and I was spearheading that project. He says, well, we've been approached about an acquisition and it looks like there's a reasonable chance it's going to go forward.
00:07:55
Speaker
You and I are the only members of the legal department to know about this and keep in mind this is not a tiny legal department. My boss, there were two layers between me and the GC and neither my boss nor my boss's boss had any idea this was going on. And so I spent the next month or so
00:08:12
Speaker
doing licensing deals by day and target side diligence by night. Stocking a data room was not easy then because the stuff was in a number of different places and just the transferring and moving of documents and things like that was non-trivial.
00:08:30
Speaker
I mean, that was sort of the beginning of my involvement in the project and it ended up doing diligence meetings around legal stuff. And just like it ended up exploding. And I was like, oh, it's not in-house I don't like. It was like it's negotiating licensing deals that I don't like. In-house is actually pretty cool. I just need to find the right opportunity. Not long after the acquisition happens,
00:08:53
Speaker
And I was like, well, OK. And about that time, I got approached about a role, basically sort of like a product counsel type role at Palm, which was the old, you know, trio, handspraying Palm, the smartphone, I guess, you know, before Apple had launched iPhone. And I got approached about basically coming over and supporting their
00:09:17
Speaker
engineering and product teams. I was like, oh, this is interesting. And I had Palm devices. I thought it was a great, great company. And this was in the middle of their reinvention. And so I went over there for two and a half years. Fun job. The company ultimately ran into a lot of issues. Started to go down the toilet. About that time, there was an opportunity with Yahoo to support their mobile products. Well, now all of a sudden, I have a lot of mobile experience.
00:09:44
Speaker
went there. That was where I realized that, OK, not even if I'm in an interesting role, like it's got to be the right size company for me. And I realized at Yahoo that I'm very much a startup guy. I prefer startup environments. So from there, I became intentional about seeking out startup roles. I ended up being the second attorney at Evernote. And I get a call from Anne Hoagie. Anne was my boss at Yahoo. She had gone to NetApp after that.
00:10:12
Speaker
And then after NetApp, she had become the general counsel of WhatsApp. And she and I had been in touch, and I'd been a reference for her when she joined WhatsApp. And she was six months into the job, and she's like, hey, I've been here for six months. They told me I can hire somebody. You were my first thought. And I'm like,
00:10:31
Speaker
Let me think about it and and so I thought about over the weekend and I'm like, you know, it feels pretty lateral to me. Like I was a WhatsApp user actually, because from I just been to I just been in Beijing for forever note and I was like, I was familiar with the product and got what they were doing. I had no idea the scale and scope of sort of the reach of the of the product and the reach of the service.
00:10:52
Speaker
And so I say, and you know, I think I'm gonna take a pass, like really flattered, happy to, you know, sort of help you identify some other folks. And here's a couple of folks you might consider talking to. And she's like, okay, yep, totally get it. That makes sense. A week later, I'm making these dates up, but it was not long after the news comes out that WhatsApp is being acquired by Facebook. And so I think to myself, huh,
00:11:19
Speaker
That might not have been the opportunity to reject out of hand.
00:11:25
Speaker
And then I started rationalizing, well, I couldn't have gotten a deal done in a week. It was way too short. There's no way I would have been hired. The funny thing is, I am 99.9. Actually, I'm 100% certain. Anne had no idea that the deal was about to happen, because that thing came together so quickly. I think she was just like, I'm building the legal function here. And then just the coincidental timing. About a month passed by, and Anne calls me back. And she's like, hey, Mark, I don't know if you heard about
00:11:56
Speaker
WhatsApp being acquired by Facebook, I'm not sure, does that change anything for you? And I said, I don't know, Anne does it? And she's like, well, I think it might. And I'm like, okay, you've got my attention, let's talk. And so one thing led to another was actually, it took a while before it all came together, but I ended up joining WhatsApp in
00:12:15
Speaker
June of 2014. So the acquisition had gotten announced in February. It was President's Day weekend. I joined in June. We didn't know when the acquisition was going to close because there were some antitrust challenges and other regulatory challenges, particularly in Europe. And ultimately it closed in, I think it was October. And so yeah, I kind of joined in the mid, the company was about 40 people when I joined. So that's what got me to WhatsApp.
00:12:39
Speaker
Tell us a little about what you expected it to be like going in, if you had any expectations at all, and then what it ended up being like working for what was still, you know, a super hard but small company within the behemoth, I guess you would sort of say that is Facebook meta. Tell us about what it would like for the before and after.
00:13:01
Speaker
That's a great question sort of all a blur at this point i think i don't know that i had specific expectations going into other than i knew it was going to be a really dynamic environment in terms of like that was a lot of change i would say candidly i had some.
00:13:17
Speaker
loose concerns that like at some point it might get too big depending on like there was a commitment from Facebook founder from Facebook's leadership to keep what's up separate and whatever separate means like it was it was clear and they did live up to this like it was going to be it wasn't just going to be immediately rolled up into Facebook and be sort of like disappear altogether
00:13:41
Speaker
And that's absolutely what happened. So I ended up being there for three and a half years. We knew that the company was going to grow. We knew there was going to be a Facebook overlay to it. I don't think I had any idea how. I knew that WhatsApp was much bigger internationally than it was in the US.
00:14:00
Speaker
I did not appreciate sort of how international my work was gonna be. I mean, such an interesting environment. Like contract negotiations were not something we were really doing. Like we were doing, like our version of contract negotiations, basically we would, you know, we would do these one sheet deals. I mean, they were full on contracts, but they were like one sheet deals with telcos for preloading WhatsApp onto their products around their phones around the world.
00:14:27
Speaker
And we had all the leverage. And so we would say, here are our terms. Sign them. Oh, I'm sorry. We need to negotiate this. OK, that's fine. We are now going to your number two. Because they will sign that, I guarantee. So we had all the leverage. So we weren't spending a lot of time negotiating contracts. What I was spending a lot of time doing, and I had no idea. I didn't have any experience in this, was dealing with law enforcement and regulatory.
00:14:55
Speaker
not yet privacy, but like a lot of law enforcement regulatory stuff both in the US and around the world. The first time I got the began to sort of appreciate what WhatsApp was like because I did a trip to Brazil because Facebook had advised us like, look, people in Brazil, but the people in Brazil love WhatsApp.
00:15:15
Speaker
government not so much, the law enforcement not so much. And you guys, WhatsApp, you have a reputation of being sort of standoffish, which was accurate. Like we were not really engaging with folks. We were focused on building the product and scaling the service and all of that. And so, you know, Facebook was like, you really need to start engaging. And we kind of begrudgingly did that. So my first, I take a trip down to Brazil,
00:15:42
Speaker
I go, I'm in Sao Paulo, I am at Facebook's outside council, and we had our own council because we were still quite separate. This was post closed, but still, everybody thought it was important that we would have our own council down there, but I was meeting with Facebook's council, and I go into the building, it was a big high rise, and I go to the receptionist, and I'm like, yeah, I'm here to see so-and-so with this law firm, and she's like, okay, what company are you with? And I said, oh, what's that?
00:16:10
Speaker
And she's like, I don't know any Portuguese, but her English is pretty good. And she's like, no, no, no, no. What company are you at? It's like, WhatsApp. And she's like.
00:16:20
Speaker
One more time. And so finally I take out my business card and I hand it to her and say, what's happened? And like you would have thought that like Mick Jagger or somebody, Beyonce walked in and she like, she stares at me and like, why not? She's like, I was clear like this, like I was a rock star. I was like, no, no, I'm just a lawyer. It's not a big deal. But it was like, it was at that point. And like, then you all of a sudden you're like, you're looking around Brazil and it was like, you know, WhatsApp is everywhere. Like in terms of,
00:16:47
Speaker
ads like WhatsApp, you know, and it was a verb there. It was, you know, it was, it was pervasive. And Brazil was one of our, one of our largest installed user bases and probably the most engaged. If you look at like how many minutes people were on WhatsApp.
00:17:03
Speaker
So I was doing a lot of meetings trying to say, you know, no, we're here. We want to talk with you and we want to engage and we want to be as helpful as we can. But they're like, well, we get questions like we want the content of the messages so that we can track down the drug dealers. And we're like, again, we don't have that actually. We don't store that. And then we launched Intend Encryption.
Leadership Challenges & Transition
00:17:23
Speaker
which totally like inflected it even more because the concerns of law enforcement like they you know there was no access to content anyways but now we're launching encryption and it was just like they were like people i i can't i can't tell you how many times i heard some version of
00:17:41
Speaker
You were doing this to thwart law enforcement. Like, no, we're actually not. We're doing this to protect the privacy of users. And because there are a lot of people and there's a lot of autocracies around the world where having absolute confidence that your messages aren't being read by anybody is really important and like life and death important.
00:17:59
Speaker
So I spent a lot of time doing, I would say, public policy type work, both before we had a formal, like Facebook was sort of advising us and we were talking to them about public policy. We eventually had a policy team that was not part of WhatsApp legal, but this was sort of in the early days. So that's what I was spending a lot of my time doing. It was super interesting, pretty stressful at times, but like some like experience like, well, how did I get here? I have no idea.
00:18:27
Speaker
Well, we'll come back to this when we get to, uh, your, your role at Twilio and some of the sort of questions that you and the team there grappled with in some ways, I think maybe, you know, maybe characterize time at WhatsApp as best of times in that sense, in some ways, worst of times in terms of the workload and burnout. And I think you're pretty open about this.
00:18:49
Speaker
take us through what was happening on kind of like the management side of the job and what was going on and how ultimately you decided to take a step back and take a sabbatical.
00:19:01
Speaker
Yeah. So I was there for three and a half years. I would say the first two and a half years were pretty, pretty like awesome, like career defining, fascinating stuff. I testified before Brazilian Congress, like weird. Well, again, how did I get here? Yeah. Yeah. I think my mom actually watched it. It was all in Portuguese. I had like a earbud translating in my ear, but like you can actually watch it online. It was sort of crazy.
00:19:23
Speaker
The last year was rough, so it was probably around August of 2016. We are now, at some point in this process, around that same time, we moved on to Facebook's campus. We had been on our own campus in Mountain View. Now we're dropped on the Mellow Park campus, which was its own sort of thing, because we had our Facebook and WhatsApp. I would tell people they're very similar in their mission. They want to connect the world. Facebook does it through social networking. WhatsApp did it through private, secure messaging.
00:19:52
Speaker
It's roughly extroverts and introverts. WhatsApp was a very introverted, quiet culture. Facebook is not. And so it was a bit of oil and water dropping us onto campus. So that was sort of in the atmosphere. More substantively, we had announced in and around August changes to our privacy policy, which was going to allow some limited data sharing, not message content, because again, we didn't have that, but metadata back with Facebook, the parent company.
00:20:20
Speaker
and all hell broke loose. Regulators around the world got pretty upset, particularly in Europe and also South America and other places. So all of a sudden we're in the middle of informal, informal inquiries all over the place. And my team, there was some Facebook folks involved, Facebook legal folks involved, and WhatsApp legal folks involved, because it was, both of us were sort of implicated. Obviously it was a data sharing.
00:20:46
Speaker
And so my team at that, I was leading the team that was sort of doing like law enforcement, product, privacy, and I figured the team was not huge. We were like, I don't know, four or five people. And so here we are, we are like writing briefs left and right. And I will say it was rough. It was rough.
00:21:05
Speaker
Procedurally like the process of generating those and like the review the amount of reviews that had to go through and here i was again i'm a startup lawyer and i'm not in the process and we're in a like a very heavy process and the other thing that's going on probably more importantly is like i am not.
00:21:23
Speaker
being an effective leader for my team. And what I mean by that is that I was very focused on getting the work done and less focused on sort of building, it was a nascent team, like people, like it was all folks who had been there for a year or two at most, in some cases less. I was very focused on getting the work done and less focused on sort of building the relationships and sort of really getting to know
00:21:51
Speaker
the folks on the team, what they needed, what they wanted to work on. And as a result, I was not an effective leader. So much so that in as early 2017, probably six months after this happens, somewhere in that range and made the decision to transition me back into a role, an individual contributor role, where I was still working on
00:22:14
Speaker
interesting stuff to me, like more on the law enforcement stuff, engaging with regulators on law enforcement, trust and safety type issues, which I care deeply about. And then also thinking more about how to integrate law enforcement processes with Facebook and also how to evolve our law enforcement posture, I would say. That stuff was interesting, but I very much
00:22:39
Speaker
felt sidelined. I basically didn't take the transition well and continued to sort of, I would say, spiral down the hill. So much
New Ventures: Segment & Twilio
00:22:49
Speaker
so that I'm struggling as an individual contributor, having performance issues for the first time in my life, in my work life, first time I've ever had any performance issues. And sort of got to the point where
00:23:02
Speaker
I was really stressed out not sleeping at night not succeeding in my job not doing my job really had become toxic you know i was like looking for anybody to blame and i think i was i don't know for sure but i got my guess is i was probably.
00:23:20
Speaker
weeks or maybe a month or two away from getting fired. I was like, you know what? I can't deal with this anymore. I decided to leave. It's a hard decision because I was leaving a fairly significant amount of money on the table, but I was really unhappy. I felt like it was a question of not if I was going to leave, but when and on what terms. I really didn't want to be walked out the door. I just didn't want that.
00:23:48
Speaker
And so I decided to leave. I was in a fortunate position where I was like, I could leave without having something lined up. And then what I said to myself, okay, I'm going to take three to six months off. If it becomes a year, so be it. I don't even know if I still want to be a lawyer. And so that was sort of like, I realized I kind of threw up on the screen there a little bit, but happy to sort of go down further on any of that.
00:24:11
Speaker
Yeah. In January 2018, I sort of, I decided, okay, I still want to be a lawyer, but I want to go be the first lawyer someplace. I don't want to, I want to go build something, build a legal function from scratch. I don't want to go someplace that's had a lawyer before. I want to go where it's a completely blank slate.
00:24:30
Speaker
And so I reached out to Craig Schmitz. He was our outside counsel at Evernote. He was a corporate startup attorney at Goodwin. And I said, hey, Craig, I'm excited to want to be a lawyer. Would love to grab lunch and like, you know, get your sense of what's out there. And he's like, yeah, yeah, yeah. Let's grab lunch. In the meantime, you should look at segment.
00:24:46
Speaker
And I said, Oh, what the F is segment. I've never heard of that. Like, so I looked, I was like, Oh, it's data. No, I've got data battle scars. I cannot do data. And he's like, no, no, you should look at them. They've been looking for like a hell of legal for a while. Really good people. I think you should check it out. And I was like, fine.
00:25:04
Speaker
And so I literally did the interviews for, I went into the process for practice because I was like, part of me was like, Oh, I got to figure out how much talk about the last year at, at, at what's happened, why I left and just sort of like the circumstances and identify practice. Um, I ended up really liking the people and sort of the things I was focused on were people, product, and size.
00:25:25
Speaker
I really had to like the people. I'm probably people one with an asterisk or one with a bullet. Product, I thought it would be B2C because that's where I'd spent most of my career. But I realized during the process, it was more about does the product resonate with me? Because I've worked on B2C and B2B products that don't resonate with me. And this product has to resonate with me. And then size, I figured it would be like 100 people, 150. Segment was a little bigger. But that was really proxy for a first lawyer.
00:25:51
Speaker
And so I ended up ultimately getting really excited about it and then took the job. A couple of things happened before I accepted the job. First thing that happened was Peter, the CEO of Segnet, says to me, hey, I want you to talk to our head of recruiting. And I'm like, I'm in no rush. I'll talk to whoever. So again, the phone with this woman, Emily, who's now a good friend of mine.
00:26:10
Speaker
And she's like, hey, we're really excited about you. We think you would do awesome here. We haven't made you an offer yet. And the reason for that is we feel like there's something holding you back. Do we have that right? And I'm like, this is not a conversation I've ever had before in this context at all or even close to it. But I'm like, okay, let's have this conversation. So I said to her, I said, okay, I think the company's great. The people are awesome. You've got this job scope just right. It's a head of legal, not a GC.
00:26:40
Speaker
I don't care about the title, I really didn't because I viewed it that would probably be my last legal job and I don't know whether it's legal. The comp was more important to me, I was selfish that way. Let's get the comp right, the title is what it is, whatever. I said you got it scoped right, all that. Here's the issue, it seems like what you really want is someone to come in and negotiate a lot of contracts and this goes back to what I said before.
00:27:04
Speaker
I don't really enjoy doing that and i'm not very good at it and so that's what you want i'm probably not the right person.
00:27:14
Speaker
And she's like, yeah, got it. That's not what we want. Like, yes, you're going to come in and the first six months you were probably going to be involved negotiating a lot of contracts because that's how you're going to get to know the business. But within six months, we expect you to be out of that day to day, probably have added, probably added somebody else to the team. And you're now like moved on and focused on sort of other bigger structural issues and less of the triage. And I'm like, okay, got it. Yes, we can talk.
00:27:41
Speaker
And so from there, kind of got very serious very quickly. I ended up taking the job, a couple of things we talked about. I talked with Peter about during this was the other thing I mentioned. One was like, look, I am perfectly comfortable with this being head of legal. If you ultimately decide you need a GC, I want to be considered for it. You end up hiring somebody else. You know, it's obviously your prerogative. Interesting.
00:28:03
Speaker
Understand I will probably leave if that happens not and I didn't say it in a threatening way I was like, I just want to be on the same page. Like, you know, I I want to be I want to be In charge of legal team. That's what I want and he's like, yeah Yeah, got it. Let's talk about like what the path to GC looks like. I was like, yeah, that's great So we had open conversations kind of all throughout until I ultimately got promoted to be GC the other thing I talked with him about was peer look I I
00:28:27
Speaker
I had struggles in leadership when I was at WhatsApp. I'm sure I will make mistakes at Segment. I need them to be different mistakes. I feel like there's stuff I need to work through and actions I need to take to ensure that I don't repeat the mistakes. I would love to work with an exact coach. And he's like, yeah, absolutely. Go find one that's good with lawyers. We'll absolutely pay for it. I've worked with four coaches myself. And so when I took the job at Segment, it was a few months down the road because I was like, I got a triage first.
00:28:57
Speaker
But the back half, so I joined in March of 2018, I think I ended up September, October was when I was able, I had hired somebody at that point and I was able, okay, now I need to work with an exec coach. That is one of the things that I did pretty early on. How did you find an exec coach? I just want to ask that because I get that question quite a bit from folks and they don't always know where to turn or whether or not the one that they're reaching out to is the right one for them.
00:29:26
Speaker
I have thoughts on that and actually some stuff I'm working on. We can talk about that later around, like I'm doing some exact coaching stuff, like getting my own coaching certification, working with some folks at Berkeley. We can talk about that separately. I do think it's hard to find, like the coach that I work with,
00:29:43
Speaker
I got we didn't have great rapport. I got a lot out of it, but it was like it's not somebody I would go work with again. Like I did get it allowed me to sort of I really sort of process what had happened at WhatsApp and sort of how I was going to really develop some principles around how I was going to approach leadership at Segment as we were building the legal team. So I got a lot out of it, but it was not somebody who I was like, oh, this is like my lifelong guru.
00:30:12
Speaker
Back to Segment. I think as many people know Segment was acquired by Twilio in a pretty blockbuster transaction. You helped make that possible. What I'm really curious about is less for us to have a conversation about the acquisition, although another time folks should ask Mark for his thoughts on that, and more sort of what happened afterwards and how
00:30:34
Speaker
You know, unlike a lot of GCs who maybe are the GC at the acquirer rather than the acquirer, you didn't take a step back and step away. You carved out a new role for yourself as their VP of ethical use. Super interesting title. Tell us a little bit about the timeline there. And then I've got a few other questions about some of the challenges you dealt with as their ethical use lead.
00:30:58
Speaker
So the acquisition closed in November 2020, so right before, like literally a couple of days before the election. My deal was I would stick around for six months and help with the transition. During that time, I had never met Karen Smith, who was Twilio's GC at the time. She and I became friends and still are very good friends to this day. We text and talk fairly regularly. Karen and I started talking about some of my WhatsApp experience dealing with
00:31:27
Speaker
thorny trust and safety issues and some of my segment experience, which I did dealt with like policy issues around like public policy issues around federal privacy and stuff like that. And, and so Karen was asking me like, what are you interested in? I was like, I was like, you know, sort of recounting some of the fun stuff I did at WhatsApp, the substantive fun stuff. And she was like,
00:31:47
Speaker
That's really interesting. And she's like, I've been sort of like charged with in this ethical use construct that we have been, you know, I've been sort of like fumbling around on here at Twilio, but it's basically the idea. So most companies in Twilio included have acceptable in segment included having have acceptable use policies. This is how you can use our service. This is what you can do on our service. Ethical use was related, but a little different. It was more about
00:32:15
Speaker
who our customers were and how they use our products and services, what they use it for, rather than the specifics of the data that might be going through the service. And so I started talking with Karen, she's like, is that something you'd be interested in helping me drive? And I was like,
00:32:33
Speaker
Well, yeah, that sounds pretty cool. Um, like hard, but really interesting. And so we started like, well, let's, let's, let's try this out. And so starting in about December of 2020, I was still formally the GC of segment as we were integrating. And so I was spending a fair bit of time on that, but then the rest of my time I was spending like trying to help
00:32:57
Speaker
Karen and help the company stand up this ethical use function, which again is all about how do we think about who our customers are and where do we draw the lines.
00:33:09
Speaker
Mm-hmm. And you brought up the interplay between sort of acceptable use policies and ethical use. And that figures pretty prominently in, uh, well, maybe one of the most prominent cases that you dealt with and the whole team at Twilio dealt with, which was early after the acquisition had closed. Twilio goes to Parler, the right wing social media.
00:33:33
Speaker
site app and tells them that they're in violation of Twilio's acceptable use policy. Take us through and end as a result, they're at risk of or are going to have access to Twilio services cut off. Take us back to that moment in time and how you were seeing it from your perspective and to the extent that you can, how that decision was made. Yeah, this was all pretty public. January 6th happens.
00:34:01
Speaker
And we learned, as everybody learned, like just through public, that parlor was a key component to the planning. We had reason to believe that parlor didn't really have much in the way of content moderation policies or practices in place.
00:34:25
Speaker
And so we basically reached out to them, sent them an email saying, and this is all public, saying, hey, we don't think you have content moderation policies or procedures in place. You have 72 hours to establish to us that we're wrong. And if you don't, we're going to terminate the service. And they came back to us very quickly and said,
00:34:47
Speaker
Yeah, we thought you might do this. We've migrated to a different service and we're like, that's great. We're done awesome. So it was an interesting was very sort of like this is all happening like in real time January 678. This was not weeks or months later. I think we sent the email.
00:35:02
Speaker
It wasn't six, but it was the seventh or the eighth at the latest. And so this all kind of was happening as stuff was happening in DC. So it was pretty fascinating. It was hard though. How you make these decisions and the process for doing it, we didn't have
00:35:20
Speaker
As even as I was stepping into the ethical use, we didn't have any of the framework that we would ultimately have. It was all and still felt super ad hoc at that point. We had sort of guiding principles, but that was about it.
00:35:33
Speaker
Talk us through the development of that framework. And I think this is really interesting because on the one hand, you want principles or you want an approach, something that you can do sort of over and over again, or to guide that internal discussion and debate. But a lot of these cases are pretty gray, not black and white. Talk us through the development of frameworks like this.
00:35:57
Speaker
Yeah, I actually really liked the process that we used for this, and it's not a process I came up with. I mean, the first thing I did was we brought in outside counsel, not to show for outside counsel, but we brought in Mark Zwilinger and Jake Sommer at Zwilgen, and they were like, if anybody has any tech policies, they are the folks. And so this was kind of, they were excited about this too, because they had done some stuff around this, but nothing like what we were about to engage in. And so we had put together a steering committee
00:36:27
Speaker
of me and Karen and one other person from legal were involved, and then several business folks. Basically, we put together this committee with the idea that we were going to distill out some principles. And so then Mark, Jake, and I put together a dozen, we gave everybody homework, we put together a dozen hypotheticals, each with multiple parts.
00:36:52
Speaker
to try and tease out, okay, where do folks think we should be drawing lines around, you know, like who our customers were and the types of content and like how what the process is going to be. And we knew that the idea of these hypotheticals was not to not that everybody would have the same answers, but that we would have some like we would hopefully have some set of situations where we're like, okay, everybody agrees.
00:37:15
Speaker
this is what we would do and some situations were on the opposite end but there would be this sticky gray morass in the middle that would require the hard. Conversations and not in the hard analysis but it was never like to think about that so this is framework which was basically it wasn't designed.
00:37:36
Speaker
It wasn't designed to be algorithmic in the sense that there wasn't gonna be like you put in this set of factors and you the answer spits out and it's clear as day and like it that was not the goal of the framework. The goal of the framework was to ensure that we were applying the same lens to these situations and we're consistently doing it.
00:37:57
Speaker
but with an acknowledgement that each case was gonna be really gray and it was gonna be close calls and people might not all come out the same way, even if they were applying the same framework, if that makes sense. Uh-huh, it does. It's really interesting, impactful work and ultimately you decided to step away from it and move into something that's totally different and doesn't require a law degree.
00:38:25
Speaker
And we're gonna talk in just a minute about maybe demystifying a little bit of the executive recruiter role and how folks can work with them. Mark has some tips there. But tell us about that decision to try something new. Was it scary? I mean, it's almost changing your identity a little bit.
00:38:41
Speaker
It wasn't scary. So the thought process on it was, so I was in this ethical use role for a better part of the year. It was intellectually interesting. But I found myself not super engaged with it. And I haven't actually ever really sort of diagnosed that, except to say that it felt tangential. And as the GC of a startup, I was used to being in the middle of a lot of stuff.
00:39:10
Speaker
And this just felt like okay i'm doing this kind of like cute little side project over here which and then that was just it felt in gentle karen had announced earlier in the year that she was going to be leaving twilio and so i'm starting to think about okay do i want to stick in this role but i'm not super engaged and
00:39:29
Speaker
and get to know and work with a new general counsel that didn't feel super exciting to me.
Executive Recruitment & Reflections
00:39:35
Speaker
And so I started to think about what I wanted to do next. And one of the things that I had gotten out of me from working with the executive coach was that I really enjoyed working with folks on career stuff and helping them think about what they want to do with their careers.
00:39:51
Speaker
And so I started to think about, oh, exact search could be really interesting. I did, by the way, think about, well, would I want to go be a GC again? And I was like, I don't know, the segment ride was a pretty good one. That's a good one to go out on, number one. And number two, the notion of being a GC in a fully remote environment really didn't excite me. I like being in the office.
00:40:14
Speaker
I'm like, if I was a GC, I'd be perfectly comfortable with folks not being like wanting to be fully remote, perfectly comfortable, supportive of that. But for me personally, like I want to be in the office like two, three, four days a week. And because that's where I would have some of the most interesting conversations.
00:40:29
Speaker
Tell us a bit more about what it entails and I guess what I'm really looking for almost is like demystify it a little bit for us. I think that a lot of folks who are either trying to get their first executive role or have had a number and maybe worked with executives in the past, they still don't have the whole puzzle put together on how to make that relationship the most effective that it can be. Talk us through any tips you have for folks who are job seeking.
00:40:57
Speaker
Yeah, so exact search and legal search in general, like we are retained search folks and not every, not every exact search and not every legal search does it this way, but most do. We are retained search. In other words, we are brought on by tech companies and other companies as an extension of them. And so we do searches on their behalf. What that means is that
00:41:21
Speaker
You talked to five different exec recruiters who are doing legal searches. You should get five different non-overlapping sets of opportunities that they are each working on. So my first piece of advice is
00:41:36
Speaker
You should not be marrying to one exec recruiter. You should be talking to a bunch of folks because you want to be on as many radars as possible is one thing. So related to that, I get some confusion around this is that folks are like, they'll reach out to me. Can you help me find a job? Well, that's not what we do. The shorthand we use is we find people for jobs, not jobs for people.
00:42:03
Speaker
Now, there are headhunters out there who will go shop your resume. That's just not what we do and that's not what most of the well-known exact and legal recruiting firms do. They are retained and do it on their own. There are some who do contingent searches and whether they don't have an exclusive on it. There is a bit of a range of things. I don't mean to oversimplify things too much, but I think just recognizing that
00:42:29
Speaker
I'm being on the radar of as many folks as possible is a good idea i think the other thing that i would say right now is is that you know it's still a tough market out there for intact legal lawyers intact as well it remains tough market it's gotten better but a lot of companies are.
00:42:49
Speaker
Going on their own right now when they're hiring especially for like non gc roles but even gc roles they're going out on their own and not engaging an exact search firm because they're like oh i've got all these recruiters sitting around not doing anything like why would i go pay.
00:43:05
Speaker
an external permission when i got salary folks here who are under under employed right now and so what's put them to work so doesn't mean you should be talking to exec recruiters but just understand that there are jobs being filled without any involvement of exec recruiters.
00:43:22
Speaker
Sure. As we start to wrap up, a couple of shorter, hopefully easier questions for you. Any book that you'd recommend folks read, whether about career or otherwise? It's a great question. I meant to bring this up before, but I'm not big on self-help book, but I'm not. I really am not. But during the sort of post WhatsApp sabbatical,
00:43:49
Speaker
I was down at a program at Stanford where I did my undergrad and the president of the university was talking about like, Oh, the most popular class with undergrads these days is a class taught out of our design school. It's called designing your life. Oh, I've heard of that.
00:44:04
Speaker
Yeah, so it's interesting. It's basically like the premise of it is, is like everybody tells you to follow your passion, but unless you're like an artist or an athlete or something like that, it's really hard, particularly for lawyers to actualize. So this comes at it from a different way, which a different place, which is let's help you figure out what your life, what you want your life to look like. How does work fit in? How does family travel, hobbies,
00:44:32
Speaker
nonprofit, philanthropic community. How does it all fit together? And so it's an active read. It's an easy read. You can take a class on Designing Your Life. So these are two design school professors at Stanford who wrote this book and teach this class. I never took the class. The book is like 15 bucks on Amazon or whatever. I highly recommend it. I've sent a lot of people to it. I do think, particularly as you're trying to figure out what do you want to be doing, I found that to be a very useful read.
00:45:01
Speaker
maybe a little bit in the same vein, a last question for you, which is if you can go back to before you went in house, maybe even before you joined the firm or very early on, any advice that you'd have for your younger self?
00:45:18
Speaker
I don't know if it's advice per se, but I wish I'd been better prepared for the challenges that I saw at WhatsApp, like in terms of like the challenges, like challenges with getting my job done and doing my job. I wish I had known that I was, that those were going to happen and that I would get through it. I wouldn't actually have ended up spending a fair bit of time like thereafter, like really sort of questioning whether I was a good lawyer or not, like all of that.
00:45:44
Speaker
like that sort of imposter syndrome. And I just wish I had known that there was gonna be a path forward. That is so unrealistic because people will tell you that until you've experienced that you really can't anticipate what it's gonna be like.
Conclusion & Engagement
00:46:01
Speaker
Sure.
00:46:02
Speaker
Well, I hope that some of the folks who are listening to this, maybe if they're at a moment like that in their careers, they can learn from your experience and know that it is possible to come out the other side and actually have an even better experience or more career defining experience afterwards. Mark, thank you so much for joining us on The Abstract. Any final thoughts you'd like to share with folks?
00:46:28
Speaker
Now, just thank you, Tyler, and thank you, Spotrat, for doing this. I do think it's a very high value thing, and I think it allows, it gives folks exposure, folks who are listening and watching, it gives an exposure to folks who have seen other things in the legal profession, and so I think it's a great service, so thank you.
00:46:49
Speaker
It's the best part of my job, the thing that I like the most. Thanks to all of our listeners too, for listening to this episode of The Abstract. Hope to see you next time. Thanks for tuning in today. Don't forget to subscribe so you can get notified as soon as we post a new episode. And if you liked this one, I'd really love to hear your thoughts. So please leave a rating or a comment. If you'd like to reach out to me or our guest, our LinkedIn profiles are in the description. See you all next week.