Matt Miller | Non-Linear Career Paths and Building Executive Teams: Insights from a Chief Legal Officer
Matt Miller, a seasoned technology lawyer and executive, is the Chief Legal Officer at Uptake, an industrial artificial intelligence software company. His past experience includes General Counsel at Bark and Green Thumb Industries, Deputy General Counsel at Groupon, law firm partner and private practice owner. Matt shares lessons learned from his recent job searches, things to consider when undertaking a job search and how as an executive, he looks to hire and build his teams.
General Counsel to Chief Legal Officer.
Marketing and networking yourself into opportunities.
Truths and fallacies of the job search process.
Three significant qualities to look for when building a team.
How can you distinguish yourself during the interview process?
Best practices when networking.
Leveraging recruiters in the legal world.
When an opportunity for a career move arises, is it the right time to move on?
Compensation; where it really ranks.
Loyalty in 2022
TOP TALENT ADVOCATES REMAINS COMITTED TO PHILANTHROPIC EFFORTS. EACH GUEST IS ASKED TO SUGGEST A NONPROFIT OF CHOICE FOR OUR SUPPORT.
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[00:00:00] Richard: Welcome to Hiring Insights. The podcast that provides insight into the executive hiring process and experience, whether you are a job seeker, a people leader, a recruiter, an executive coach or simply interested in talent. There is something here for you on the Hiring Insights. Today's episode is presented by Top Talent Advocates, where we advocate for executive and legal talent.
You can learn more about Top Talent, listen to other episodes and hire great talent by visiting www.toptalentadvocates.com and clicking on podcast. Now here's your host for Hiring Insights, Mosah Fernandez Goodman.
[00:00:44] Mosah: On this episode, I'm joined by Matt Miller, who's a chief legal officer in Chicago. Matt will share with us lessons learned from his recent job searches, things to consider when undertaking a job search and how as an executive, he looks to hire and build his teams. Matt, I can't tell you how happy I am to have you on the show today.
I've been impressed by your background and getting to know you over the last year or two, for those of us who might not necessarily be familiar with you or your career path, would you be willing to share how you got to where you are today, some of the things that motivated you to get there, and just give us a brief background on yourself.
[00:01:27] Matt: Happy to do that one, thank you for having me. I was flattered to have the ask for my first podcast episode. I feel like that should be celebrated somehow in some way, and I'll figure out a way to do that this weekend.
I have been practicing law since 1996. I have practiced in that time in just about every way you can practice. I started at a big firm in big law, general law. I went from there to a smaller shop, a litigation firm. I have had my own firm three separate times. I have worked in a mid-size Chicago full-service firm called Much Shelist. I've been in house now since 2011.
I started at Groupon, I had a couple other opportunities along the way. And then most recently was at Bark, a company that went public by way of SPAC. And now I'm currently the Chief Legal Officer at Uptake Technologies.
[00:02:16] Mosah: Matt, I've gotten to know you over the last several years as both a friend and someone who I've helped work with during their search. I'm wondering if you might shed a little bit of light on our backgrounds so that listeners know the context of how we came to know each other.
[00:02:30] Matt: Sure. You know, in part of my networking and when I was trying to figure out what to do with my life, I had reached out to a recruiter, legal recruiter who was really kind with her time.
Really helpful with advice but couldn't help directly, but just gave good overall career and life advice and included in that was you should talk to this guy, Mosah Goodman, at Top Talent Advocates. So I did, I reached out to you. I remember you actually thinking, I think your first response was how'd you get this email, something like that.
How'd you get this as people are usually referred to me and I had to explain that, but it was a great call, and you were explaining to me what you were trying to do. Your analogy of a sports agent for executives. And I thought that's exactly what I need. This is what I've been looking for the past number of months.
And so I was really happy to have that introduction, but at the same time, I don't pretend otherwise, I think I can be a difficult client sometimes for someone in that view, in that I have an active network. I know what I want to do. I know how I want it to be. I'm not necessarily going to follow the usual customs and ways of doing things.
And you were okay with all that. You know, we were able to customize as I needed your help. I want your advice, I need your guidance. How do I make my paper better? My resume, my cover letters. How do I prepare for this interview? How do I handle this question? How do I deal with this thing in my background, or and then when I was leaving Bark.
To go to Uptake after less than a year of Bark, talking that through with you, how do I handle this and how do I manage the messaging? And so you provided that for me. And you also helped prop me up at times when I was feeling down on I'm not going to get anything, I'm going to be a retired lawyer and I'm going to do something non-law and you would prop me up on we'll find something, or, what about this opportunity?
Or have you seen this, or have you talked to this person? Did you reach out to this contact of yours yet? And so it's hard to put a price on that. Although of course you do, but it's one of those things where it's like everybody should do it. And when I talk to people who are looking at it, I refer them to you, and this is not a paid advertisement and you didn't ask for any of this, but it is truly what I think.
And people do reach out to me from LinkedIn or from other things and say, hey, can I talk with you about your job search or your journey or how you got there? And I do, and always included in those conversations is, and you should talk to this guy, Mosah.
[00:04:49] Mosah: Can you share with us a little bit about your role at Uptake and maybe a little bit about the company.
[00:04:53] Matt: I'm really happy to be at Uptake. I truly love what I do and who I'm doing it with. We are a tech company, so coming back to Uptake, put me back in the tech world, which is what Groupon was, and that was my first in-house role. And I really enjoy the tech space generally, and the people that it attracts. Uptake is an industrial analytics company.
We do sort of artificial intelligence, machine learning and help industries understand and better use their data, which can help them save money, save time, reduce carbon footprint. The opportunities here are positive. And so that also was important to me. As Chief Legal Officer at Uptake, I have a seat at the proverbial table.
I am one of the executive leaders there. I really have a great group of executives that I work with. That's what makes it all worthwhile, right? We have this great leadership team. We've got great talent throughout the company. Really smart people in a phenomenal culture that has survived and thrived even during the strange pandemic days.
That's the 30/45 second overview who we are, what we do and what I do. I mean, the legal issues cross everything you might think employment, regulatory, privacy, contract, commercial, you name it we have it. And the industry is a hot industry and AI was science fiction 15 years ago, and now I'm working in it.
So that's pretty cool.
[00:06:15] Mosah: So Matt you've recently switched jobs at the time of this recording. And you've now landed as the Chief Legal Officer at Uptake. Can you tell us about the last few years of your career and sort of how you got to where you are today?
[00:06:30] Matt: So as I was sort of reviewing my circuitous background, I had mentioned that I was at a point where I started exploring general counsel opportunities. This is in 2018/2019, thereabouts. Those opportunities are hard to find, right? Every company has one and it's not easy to find your first. Sort of like a head coaching job at a professional sport. It's hard to find your first, once you find your first, maybe you can get your second and third, but that first one's tough.
So I started searching and networking and doing all I can to find an opportunity and that landed me at a company called Bark. And that is an e-commerce company serving dogs. And at the time the company was beginning to go public by way of SPAC. Which I did. They're based in New York, I'm here in Chicago. And while I was working there, I had an opportunity and had been contacted by Uptake Technologies about an opportunity to come back, to work in the ecosystem.
That's my term, the ecosystem of the companies founded by Brad Keywell and others. Brought me back to sorta to the same address at 600 west Chicago, back working with Brad and would keep me in Chicago. So that was an opportunity. That to me was one I was not going to pass up and, and that's where I've been since September of 21.
[00:07:48] Mosah: Can you tell us a little bit about those jobs searches and maybe focusing specifically on what you did to market or network yourself into those different opportunities?
[00:07:58] Matt: Sure. It's a stressful process and there's a lot of, for me anyway, was a lot of trial and error, maybe more error than not, but that's just sort of the process, because there are sort of phases that you go through.
Panic, what am I going to do? Maybe I just should go be a bartender. I can't find work. And maybe this law thing is just not going to work out. And all my different choices were going to be a dead end. Those thoughts were real. And anybody listening to this who's going through that process, I mean, those are very real thoughts and very normal.
And I think people who are searching for a job, all experience it. So what I tell people having come out of that myself is you do have to be patient, as hard as that might be, because something will come your way. That sounds more passive than it actually is. You will find something that will work for you. Whether it's a long-term solution or just something to mine some time, while I try to find something else, you will find that opportunity.
It was a lot of networking for me, and that meant being very active. On LinkedIn, not just posting, although I was doing more of that, but also watching what was happening in the legal community. Who was leaving a general council job or where what companies were maybe spinning off new subsidiaries.
And then looking at job listings on LinkedIn, on other email servers, on any source I could find. And then taking that information and if I saw a company looking for general counsel, then going to LinkedIn and finding out who do I know there? Do I know anybody or do I know somebody who might know somebody there so I can get an introduction, find out more about the opportunity.
If it seems like a good one, then obviously it's nice to have that reference. If you can have somebody, you know, putting in a good word for you. I was very active in that, doing that sort of work. I reached out to some recruiters along the way, would share my resume with people who influenced me along my career. I let them know that I was looking. Because the people that don't know, they can't help. You'd be surprised at how willing people are to help if only they know you actually want the help Which does mean swallowing a little bit of pride and, you know, and talk about wherever you are in your journey. So, in a nutshell really, that's what it was for me.
I describe it, I see it in my mind as I ignited my network. Like the neural connections were working and lights were going off and people were connecting, and people wanted to help. I was helping them help me and a big part of my days were spent working in that network, interviewing and pursuing opportunities and being as active as I could in that regard.
[00:10:23] Mosah: You talk about your network. Did you grow your network during your search and were you meeting new people and expanding it? Because a lot of the work that I do with candidates is helping broker and network new introductions to folks who might be of assistance. And you never know where that sort of magic bullet is going to come from.
But can you share a little bit about how you might've grown your network?
[00:10:46] Matt: I mean, I mostly relied on my network as, as it was, but I absolutely grew it. I mean, I met you through that process. I didn't know who you were. You didn't know who I was, but you know, I had reached out to a recruiter. I don't remember how we were connected on LinkedIn.
I don't know how or why I had reached out to her, and she connected me to you and you and I had a good conversation. And, you know, you were incredibly helpful for me, a great sounding board as I went through that process. But I was really more focused on my network working. And then through that, of course they would introduce you to people or opportunities.
And so your network would grow that way. But I did try growing my network in ways that in hindsight for me, weren't right. Because I think the key takeaway of all of it for me and that I would tell folks, listening or people who call me for advice individually, is you have to be natural to yourself. Some of the advice I got from some people was join this group, you know, and go here and attend their meetings.
I'm not a joiner. It's just, you know, never a student council guy, it's just not my thing. But for some people it's highly valuable and has helped to find their career. But I tried it and I attended some meetings and it was largely a waste of my time, and connections I made there weren't natural, so they didn't stick. Right?
I wasn't meeting people in a way that was natural to me. So that was not a good way for me to grow my network. I would grow it by someone like yourself or others, who I was talking to, who either knew or met and connected with. An introduction being made that way I would take whether it was for an opportunity or if they knew of an opportunity. That was helpful.
Because if I got an introduction to somebody, I didn't know, so a new network connection from somebody who we both know and respected, that's a natural connection and that really worked. But the other thing that really surprised me is there were people who I didn't know, would step up and go to bat for me who did, and there are people who I thought, God, this person is going to be incredibly helpful and they weren't.
Sort of the same, less than I had when I was starting my own law firm and trying to generate businesses, you'll be surprised, which is why you have to let people know you're looking. Because you're going to be surprised that the person you worked with 10 years ago or you were in law school with however many years ago, is going to actually be incredibly helpful and connect you with with people, an opportunity.
[00:13:00] Mosah: Matt it sounds like you were your own best advocate in helping go out and network and let people know that you were interested and excited about what opportunities might be out there. How much time did you spend networking? If you had to allocate sort of a percentage of the pie, if you will, to the amount of time you would spend contacting recruiters or networking, or simply applying online. Can you give some insight into both what you found to be most successful and how you kind of allocated your time? Because that's everyone's most precious commodity.
[00:13:34] Matt: Yeah. I spent probably too much time on it and some of the advice I received, which was good advice, that I did not follow was don't spend all day, every day on this it'll drive you crazy.
Doing it will really play mind tricks with you. You’re going to be sending out resumes and talking to people and you're not going to be getting every opportunity. Maybe you don't get any interviews for some period of time, but I had a hard time resisting the allure of letting me do it. One, I like it. I enjoy it.
I like talking to, meeting with people and seeing opportunities and throwing my hat in the ring and seeing if I can get an interview and landing off, right? There's something about that, that I enjoy, but I spent too much time on it to be honest. And I think anybody listening to this is also probably going to spend too much time on it because how do you not? You're trying to define your career.
The way I balanced it a little bit is I also, because I wasn't doing anything for a period of time, I started a law firm again. Not hard to do these days, right? I mean, I've got a virtual office, I set up an address and I started doing some work. And so that kept me a little busy.
But my number one priority was I want to find something and no one is going to find it for me, or choose your expression, you're your own CEO or believe in yourself or advocate for yourself.
Choose your pet. Choose your adventure. Whatever it is. Nobody's going to find that for you. So it was pretty all consuming. I was worried about the process. I was stressed about the process. It was incredibly stressful to figure out what am I going to do? I got to find something.
[00:14:57] Mosah: So let let's talk about how you got started in your search.
Often when I'm working with clients or candidate. We start with some form of goal-setting, but then we quickly move into developing the tools, right? LinkedIn, cover letter, resume, job search strategy with candidates. And so can you share a little bit of light on how you did that? And if that process was helpful to helping you be more efficient in your search, the value of those tools, as it worked to either clarify in your own mind or in the minds of those that you were networking with.
What you were looking for and really what you brought to this?
[00:15:34] Matt: I mean, the first thing I did was take a breather, which I think is important. And I would advocate to anybody who's in the position to do that, whether it's for a couple of weeks or a couple of months, you don't have those opportunities all that often.
And if you can take it, you should do it and reset. And for me, that was important in particular because as I mentioned, I'd taken an opportunity that just wasn't a good fit for me and I just needed to reset. So that was the first thing reset, recalibrate, what are my goals? What do I really want to be doing?
And that was important in the beginning. I think my approach was I'm going to find opportunities. I'm going to apply to them and something's going to happen. I learned the fallacy of that pretty quickly, right? I mean, you send things out, you don't even hear back and you don't know why, because on paper you think, gosh, I think I'm pitch perfect for this, this should be great. And so I didn't really form a strategy until probably, until I got introduced to you and some others around that same time. Okay, you got to really think about a modern resume and how do they work and also web crawlers, which is what all the recruiters now use. How do you make sure your resume is going to answer the things and changing it based on different jobs you're going to apply for, not the guts of it, but there are ways to set up your resume.
So you've got, I think for me, I had set up a skill or a skills and qualifications. I can't remember the exact title, but some subject at the top, which had maybe 12 keywords, that made sense when you were reading it, wasn't just key words that like a bot would read and it made sense. But I might adjust it depending on what I'm applying for.
If it was an international job I might've put on there, you know, international experience, if it was a job that was going to be heavily focused in a consumer facing industry, I might add that up there. So I started to develop that strategy of make sure your resume is individualized, but not so much that you're spending hours each time you apply for a job because you're going to run out of time. So structuring it in a way, that the body stays the same, but you have some things you can play with. Leverage you can pull for different applications and same with a cover letter, right? Write a cover letter that's got a couple of sentences that maybe you change each time.
That became very important to me. And then I started to define things that also matter to me, I wasn't going to move from Chicago. That mattered to me and I had to stay true to that. Remote would have been fine, but so there were certain things that you just had to be true to. And as I was targeting opportunities, I would just keep those front of mind so that I was pursuing things intentionally. Because also I think when you're interviewing with a place, if it's not genuine, it's probably going to show.
And so I think that's what I did was trying to tailor my documents, but write them in a way that I wasn't starting over each time, but that they could be customized pretty simply. And also being, having in mind-front of my mind, what are the things that are going to matter to me, trying to decide does title matter?
Will I accept a deputy general counsel or an associate general counsel position for the right opportunity at the right company? Am I going for title, am I going for opportunity? So those are the things you have to keep in mind as you're looking at opportunity.
[00:18:31] Mosah: So what surprised you about your search?
Maybe some things that didn't go as planned. I know you mentioned that some people were more or less helpful than you would have anticipated, but can you give us those moments where you were pleasantly or unpleasantly surprised with part of the search?
[00:18:46] Matt: Yeah. I'm going to start with a pleasantly because why not start on the good notes and it's really meaningful to me.
I was amazed, pleasantly surprised I guess, at the number of people who really did the help and were people who, you know, I hadn't talked to some in many years and they were not just saying, sure, if I hear of anything I'll let you know. But actively helping me and connecting me with their networker or making introductions for me.
You were passing opportunities along to me and that was amazing. And when you're in that stressful position of what am I going to do next to know that even though you might feel like you might have to just be done doing what you do for a career, people actually think highly of you and are going to try to help you. It was definitely a great surprise and a huge benefit, and frankly, necessary to the process because the confidence gets shot.
So that's what it was for me. I'm forever thankful for the folks who helped me along the way. And I think they know who they are.
[00:19:40] Mosah: Thanks, Matt. And so what were some of the thing that might not have gone exactly as you had planned or it might not have been as positive experience during the search?
[00:19:49] Matt: To the downside.
I'm amazed at the number of people who just don't respond to candidates. Even if you go through the process and have interviews, even a second round of interviews and they have no idea why maybe you're not selected and that doesn't help anybody because you're not learning. So that surprised me.
Maybe it shouldn't have, maybe that was naive of me going in. And then I pretty quickly learned it is a little bit of every man and every woman for themselves in the job searching process. You got to get used to rejection because you're going to be rejected many times, even for things that you think you were perfect for, or maybe you'll even think you're better than the person who you end up seeing lands the job and you know, better being subjective.
Maybe not the best word choice there, but the idea is conveyed. That is deflating, right? You send out resumes, even maybe you have a connection and a network and you get an introduction and you apply, you interview and you don't get it, that happens once. Okay. But it happens twice, three times, four times, who knows how many times, it can really discourage you.
It's hard to keep going, but you do have to keep going. You're going to have opportunities where you're going to, or I did anyway, you'll have an interview. It'll feel really like it went well and you'll then be told probably directly through a recruiter, probably not even directly from the opportunity the employer had sent themselves, that you're not selected or you're not going to go through, and you don't know why.
And so, you don't have an opportunity to learn or grow. You've got to guess. And so that was also discouraging and a less than pleasant part of the experience I would say. But the main thing is rejections hard. If you're looking at a job at a certain level, at the levels I was looking, you have competence, you believe you're good at what you do.You like to think you're good at what you do and you get knocked down because you know, there's a lot of no, tons of silence. That's no fun either. So that, to me, that's the biggest negative is the rejection and the ghosting.
[00:21:44] Mosah: You talked a little bit about wanting to have a positive impact on the teams that you're a part of and the teams that you work with.
I'd like to gain your perspective on the other side of the hiring table, if you will, and talk a little bit about how you view candidates and how you view the composition of a team and how you fill the gaps on your team. So, when you and your peers are hiring your teams, as a member of the C-suite, what are, if you could, the three most significant qualities or experiences that you're looking for in candidates? What are those things that really jump out at you as necessary components to help building and rounding out teams?
[00:22:26] Matt: Sure. Great question. And you know, my answers are all going to be through the lens though. I've been in the startup world since I've been working for companies from Groupon to when I was in the cannabis company to Bark, to now Uptake, that's the prism through which I see it.
And what I think people are looking for when they're hiring in those environments is individuals who have a broad background. Who have tried different things, done different things. Because you're going to move really fast. When you come into a high-growth environment to startup environment or any high growth environment, you're going to move really fast and they're going to be opportunities to grow and do new things and get outside of your comfort zone.
And so you're looking for that breadth of experience, the willingness to try things and something that will show that this person, this candidate can succeed in an environment where the job might change and it might change quickly. And there might be opportunities to change with growth. If they're willing to try something new and they believe that they can do it, I think that's one thing you're definitely looking for.
You're also looking for people who will come in and be the proverbial good team player. You don't all have to be best friends. You don't have to be friends necessarily. I mean, that's a different concept when you're working, but you have to be able to work well together.
You have to trust and respect the people you're working with and so that everybody has a voice, so that all ideas can be heard because that's the only way progress happens. If you have somebody who comes in and they're going to shut down all their voices and think that only their way is the right way, that prevents progress, that prevents growth for the company that prevents growth for individuals.
And that just makes it an unpleasant working experience. And we all spend too much time at work to have to deal with that. I think that those are the two things I would emphasize the most sort of breadth of experience, or at least a demonstrated ability to do that. And somebody who you believe in. It's art, not science, I think is going to be a good team player.
It will be additive to what you're doing.
[00:24:25] Mosah: How can a candidate distinguish themselves during the recruiting process or how can they get noticed? What gets your attention? And I think I'm curious because you interview both lawyers and non-lawyers to join a company. Can you talk about it just generally from a candidate’s perspective, what gets your attention?
How can someone distinguish themselves in helping join an organization that you're a part of leading?
[00:24:49] Matt: I do of course candidly interview more lawyers than non-lawyers, but I have over time helped people with their interviews. And especially when departments that work closely with legal, that want the legal team or representatives to interview their candidates for me, I am looking for you know, how does somebody distinguish themselves? One, is be yourself and be candid and comfortable with who you are. Don't try to be what you think the interviews are looking for because one, your guess is probably going to be wrong. You're going to interview with different people who bring different personalities to the table.
So, I want somebody who's coming and they're bringing their whole genuine self to the process. I like the conversations to be natural and yes, we're going to cover a resume, but if we're not covering the resume and instead, we're talking about that summer, you spent as a longshoreman off in Alaska, that's also awesome. I want to hear about that. I want to know those experiences. Not that we're not going to talk about the guts of what the job is and what you're expected to do. But I want to know who is this person that we're talking to that’s going to come and join our team. Are they going to help us professionally with whatever it is they're being tasked to do?
And also, are they, is this going to be somebody who's going to add to the personality of what we're doing? Our culture, everybody talks about culture. It's this, what is culture? However you define it at the end of the day, it's the sum of the parts of the people you bring into the table. And so that's, to me, the number one thing, be genuine, be yourself, be honest about what you're trying to do.
I'll put it in the law department. If I'm interviewing somebody who says, I want to be a general counsel, I want to be chief legal officer. I want to know that. I'm not going to feel threatened by that. I'm not going to. I want to know that because now I know when the person is ambitious and has goals and I want to help that person get there.
And that might mean they're going to leave in three years because you know, I'm not going anywhere, but I want to know that I don't want somebody coming in and saying, oh, I just want to work for you forever. And that's not genuine, and I'm going to feel like you don't really want my job. You just want any job.
So, you have to convey that the job that you're interviewing for is something that you uniquely want. The good and the bad that come with it, right? You don't want it just to seem like I'm just looking for a job, any job. So, you have to be honest, you have to be genuine and you have to take some risks. You know, there's people say, when you're being interviewed, you're also interviewing the people who are interviewing you.
And I agree with that fully. Ask hard questions, ask real questions, ask about trajectory. Um, I think those are the things people want to know that you care about.
[00:27:09] Mosah: So, if you wanted to get hired by yourself, if you were a candidate looking to join one of your teams, what would you do to get noticed or to network in?
What advice would you give candidates? And obviously this is intended to convey to people some best practices. And my hope isn't that your inbox gets flooded, although it might, what's some guidance or tips you would give?
[00:27:31] Matt: I would say, I mentioned that the way I was envisioning when I was, when I was doing it, that this neural network lighting up, right?
This maps lights going off all over the places when I'm envisioning like a sci-fi movie, do that. Light up your neural network. If you say, I want to get to Matt Miller and I want to talk to him about Uptake or, you know what, I don't want to be at Uptake, but he was at Groupon, I want to talk about that. I want to know what his experience was about that, find that connection.
It's very hard to keep up with all the people who reach out to you. I try to respond to people, but so many people reach out directly through LinkedIn or otherwise it can be hard. And so, you really do want to find that connection of somebody who can say, hey, you know, my friend would be really interested in talking with you or something, or maybe it's just through your law school or your undergrad or through something.
Find a common connection. And that's the best way. And I wouldn't expect a hundred percent hit rate on that when you're doing that and activating your network. But to me, that is the way you get the attention. Because the blind resumes that are just thrown in, they certainly worked sometimes for people, no question about it. You should do that. But if there are opportunities that are particularly interesting to you, you have to spend time on finding where does my network connect here? Where is it as strong as you can make it? So I would, if you see an immediate, like LinkedIn has those second or third degree connections, is their terminology, if you just stop there, that's not enough.
I would dig more. And you know, you're digging through your LinkedIn, you're digging through the social media to see who, who can really help me meet Matt or meet whoever it is I'm trying to meet. That would be my advice. That's how you get noticed. It's not the random emails. It's not the, the clever things you might put it in subject line.
Sometimes it might be those things, but the best way is to find that connection.
[00:29:10] Mosah: That's so true. And that that's obviously what we do for our clients all day, every day has helped make those introductions. Either putting our, our sort of seal of approval on it, or working with others to help them broker those introductions
[00:29:25] Matt: Yeah. And sometimes if it's not under the cover of, I need something or just, I want to learn. I have something right now where recent college graduate, who I knew, whose family I know, is in a similar industry and wanted to talk about some things and it wasn't a, Hey-can you talk with this person about how'd you get to where you are, especially since I have a non-traditional path, right?
I wasn't Harvard and then Yale, and then all these fancy things and then be at a fancy law firm forever and be partner and then be chairman of something. I mean I had a nonlinear path. And so, to reach out under cover of, I just want to make the connection to talk about how you got to where you are, or somebody said, you'd be a good person for me to talk to this person that we both know.
That is great. Don't over ask hey, can you get my neighbor, my friend, my cousin, a job. That's an over ask.
[00:30:16] Mosah: So, Matt, I'd like to talk a little bit about recruiters and your, your focus being in, in the legal field. We'll focus primarily on legal recruiters. So can you share with us a little bit about when, as a CLO, chief legal officer you'll engage a recruiter when you start to consider engaging a recruiter, as opposed to working through normal or non-recruiting-based hiring channels?
[00:30:43] Matt: I have never used a recruiter in hiring in legal. I just haven't had a need. So when would I consider it? I would consider it if I'm not finding the right candidates for a particular role, for whatever reason, like maybe I'm just not finding the right qualifications or maybe there's a geographic limitation, but if I'm not having success over a reasonable period of time, then I would go to a recruiter.
I have a very good inactive network. And when I post jobs, I get responses. And also, there aren't that many opportunities inside of companies in terms of the demand and the need. So when you post something, you're going to get a lot of resumes. I've just never had a hard time finding really qualified, really good candidates for jobs.
So I've never used them. I would only imagine using a recruiter if I just can't find somebody that I need.
[00:3:29] Mosah: What about as a candidate, as someone who had been looking, how did you, or leverage recruiters and what was your experience like in working with or making outreach to recruiters? Maybe there's more experience there to shed light on?
[00:31:43] Matt: Yeah. I had a lot of experience there and I will say that from a candidate’s perspective, the recruiting industry is broken certainly from a perspective of somebody who wants to work for a company. It's different if you're trying to move from law firm to law firm, where recruiters will help you directly. In the corporate world, recruiters are hired by the companies to go find candidates.
And so reaching out to recruiters, this is something it's probably a necessary step. I did it. I would submit my resume. A lot of them have online portals, send us your resume, do that. I sat and had lunch or drinks with some recruiters. I did all those things. 90% of them turned into not even a good relationship, just nothing.
There was just sort of probably an hour loss for all of our time. Some recruiters were helpful. Even though they’d be very honest, and this is sort of one of my themes through this discussion, be honest about what you're looking for and trying to do. And some recruiters are really honest. They say look, I would love to help you, but I'm working with/for the companies and I have specific directives and I don't have anything here, but you know, one of the recruiters introduced me to you.
And so that was a huge value to me. But a lot of them will just say hey, I don't work for you. Send me your resume. I'll call you if I think of something. And I think that they don’t, and they won't. Their bread is buttered by going to the usual candidates and hiring people out of high-level positions and high profile and moving them around, but it works. Again, back to the analogy of head coaching in professional sports, right?
When, once you're in, you can coach the bears one year and then a couple of years later, you're coaching a different team.
[00:33:08] Mosah: And if you're not successful, you'll coach New York Jets.
[00:33:10] Matt: Or the Detroit lions, or maybe you'll take that step and go to college and then come back up. So there are a lot of things to me.
If I'm talking to somebody who's really looking hard for their next opportunity, I'm not going to be telling them you should be really investing in recruiters. You shouldn’t invest your time there because I don't think the recruiters are going to pay attention to you. And I think that's unfortunate because when you're looking for a job and you're in between you're vulnerable, you're in a vulnerable state of your life. You're worried about your bills, your mortgage, your kids, whatever your life circumstance might be, or you're worried about how am I going to make it keep working? And you'll just not get return phone calls or people will kind of give half a try.
If they're recruiting for something they're just not going to vary from the specs they were given. I did not meet any recruiter who was willing to say Matt, I think you're awesome, but you're not exactly what this client wants, but I'm going to see if I can get them to talk to you anyway, because I think you'd be a great fit.
Which is to me sort of most, I think, a little bit what you do, but certainly not what the recruiters do. And that was a little bit discouraging because you talked to somebody like, I know I can do this job and I know you're telling me what they want is they want this degree, or they want this number of Superbowl trophies. I get it.
But I would say, you gotta do what you gotta do. So sure, it doesn't hurt. It takes five minutes to go online, upload your resume to all their portals, do all that kind of stuff. If somebody introduces you to a recruiter or you have a chance to meet one and have lunch or have a coffee or have whatever, it is what you want to do with your time, you can certainly do it.
But on the, on the list of things that are likely to be successful, that's not going to be high.
[00:34:39] Mosah: So, Matt, you left Bark. I think within a year of becoming their general counsel. And I think for some of our listeners, they might view that as, as a quick change and perhaps even stigmatize it a little bit. Would you shed some light on the sort of process that you went through and thinking about leaving a job by what all accounts is, is quickly, and how you think people should consider those types of opportunities?
And when they, when it's okay to do that.
[00:35:09] Matt: Yes. Great question. You have to be thoughtful about that stuff. I mean, it was a quick departure. So people who think that would be thinking correctly. On just math, it was quick departure, but I think that the stigma around that is dated. I don't think that that matters that much anymore.
It doesn't mean you should job hop. You should not job hop, but opportunities come up when they come up, you cannot control that. And you can't forego an opportunity. That might be the right one for you because you feel like it's going to look like a short time to somebody, whoever that somebody might be.
That that cannot be your measure, but you have to be thoughtful and considerate about it for yourself. Like, is this the right thing for me to do? Am I going to put myself in a jam? And also others, like, why am I doing this? So you got to think about how would I explain it if somebody, like Mosah Goodman brings me on a podcast and asked me about it, how am I going to explain it?
And for me, that was, I went through all of that analysis, and you know, the opportunity to come work at Uptake a Chicago-based company, with people who I had known for 20 years. The founder of Uptake is Brad Keywell. And I met him on the opposite side of a case and then worked in Groupon, which is another company that he was part of the founding team for.
That was just a great opportunity for me. And one that I certainly wished it had come up at a time when there wasn't going to be a short stay interruption, but I don't control that. I have to make sure that when I'm leaving Bark, I do that on good terms and do it the right way. And I tried to do that.
And I hope I succeeded in doing that. I had onboarded the lawyer there shortly before I was leaving. I felt like I was leaving them in a good spot. And of course, I wanted to talk with the person I hired to make sure he understood what was happening. Try to leave it all on good terms, knowing that I can explain to folks that this is a better opportunity for Matt Miller.
It may not be for everybody, but for me coming back to work with people who I admire and an opportunity that I think is fantastic in an industry that I think is high growth and it's very relevant and very timely, and also gave me that opportunity to really rise. Chief legal officer, as opposed to general counsel, which I was at Bark, which might seem minor to some people.
But to me really mattered because I wanted to do more than just lead legal. I wanted to be part of an executive team and have that voice. I'm not going to say I wasn't worried about the shortstop. It was on my mind, but I wasn't going to let that stop me from pursuing an opportunity that, that I think is a great opportunity that I think I can explain well to people when they say, what, why would you do that?
And also leave the right way, always leave the right way anyway. But particularly if it's going to be relatively short, you want to make sure you leave the right way. But at the end of the day, it's your career. If somebody's feelings are hurt by what you did, as long as you're not trying to hurt their feelings, but their feelings get hurt, you can't control that.
And you really can't worry about that too much. You know, their companies, aren't going to worry about it when they say hey, we have to make some changes and we're rearranging. We don't have a job for you anymore. They're going to feel bad and they're not gonna wanna hurt your feelings, but they're going to do it. Same way for yourself.
Don't be rude. Don't burn bridges, but also don't worry too much if somebody feels bad about what you did. I don't know that there's that much stigma anymore to short stays, you know, the idea of staying for 50 years and getting a gold watch is not a thing really anymore. You just have to be able to make sure you can explain what you're doing.
That has to make a lot of sense. So people understand that its objective and goal-driven that you are loyal, but that you don't control when opportunities come up, but you can't pass up an opportunity. Cause gee whiz, what might somebody think.
[00:38:37] Mosah: Matt, one thing that a lot of people are factoring into their decision when they're making moves in their career or looking for new opportunities is compensation.
And you and I, over the course of our work together, talked about that quite a lot, because it's an important factor. It's not the only factor in someone's job search. I'm wondering if you might shed a little bit of light from both sides of the table, as an executive who makes and extends offers and as a candidate, how you think about compensation and some of the things that others should be thinking about?
[00:39:08] Matt: Well, great question. Obviously it's always top of mind for people. I think when you said that it's an important factor, but not the only factor that's sort of the key right. Compensation matters. You should know your value. And you should want to be paid your value, but that can't be the only thing, right?
Because if there, there might be some opportunities that will pay you more than other opportunities, but it's just, you're not going to like the culture. You're not going to like your life. They're going to want you to do things that aren't gonna fit the rest of how you imagine your days. And so it can't be your only factor, but you do as a candidate.
I'll talk about that role. First, you do have to have some idea of what is my worth in the market, and you're gonna have to define that market yourself. Is that a geographic market? Is that a job role market? What is it? Is it a public company market versus a privately held company market? And you're going to know that just from peers and other people, maybe other jobs you've had, and you should not settle for anything less than that.
With an asterisk, the asterisk being, unless you have really good reason to do it, like you love the opportunity. You think that maybe you want the experience that the company is going to provide, and maybe you don't see it as a long-term solution for you, but Hey, I really want to get experience in this industry.
And so even though they're under market, I can do this for a little while, but my warning to you then would be, don't forget your goal, which is that's not your longterm answer. So if you take something like that, cause you feel like, hey, I really want to get experience in this industry. Then, a little bit underpaid.
But I'll get the experience and then I'll move on. Don't forget that-then I'll move on part. Meaning you have to start your networking and you have to start building your brand because otherwise you'll find yourself under compensated for far too long. And you'll go way past your, your shelf life of, I want to get the experience.
You'll have the experience and the candidate world. You have to know your worth. People are going to give you different answers on what that is. West coast-folks might say some based on some percentage of the company and what your role is. That's too complicated of math for me. I always just had numbers in mind.
Like I think the numbers about this based on peers I talked to and things I know, and that's what I was looking for from the hiring. I want to know candidates know their worth. That tells me they one, they value themselves and their belief in themselves. It also tells me they've done their homework. They know what, what the range is ought to be.
But I also think, you know, employers should pay their people fairly. We try to do that at Uptake and everywhere I've been, we try to do that. You want to make sure you're paying people fairly, that might depend on, uh, on a different, you know, mix of things. Is it, is there equity involved? Is it public company equity or is it private company equity that may or may not ever have any value, but it's going to be a mix of things.
It really does bother me when I see employers. And when I say see employers, I mean, things you see people talk about on LinkedIn, how companies might try to get people on the cheap. I think I saw somebody put it as they want to get rockstar singers for backup singer prices. And that's just the wrong way to do business.
So I think that you shouldn't do that because if you're doing that as an employer, you might get people in the door because maybe they want that experience, but maybe they just need to get it. They've been out of work for so long. We just need to get something, they're not going to stay. So you're not going to build any really good culture, the dive and save in the end zone to use a term that I, that I like and have adopted.
Right. So, you know what I mean by that is somebody leaves and say, oh, Hey, we'll pay you more money. That's too late. They might say, yeah, But all you're then doing is buying some time before they leave again. Why not show people the value in it at the beginning? You know? And if somebody then finds some position that pays them more money, maybe you gotta be okay as an employer with, with them going to pursue that.
Cause that might be outside of what you think the market is. Right? And so everybody's gotta be reasonable and try to free people the right way and respect the decisions that people make. Um, if they have different views of what the market ought to be, but you know, the summary for the candidates is don't sell yourself short.
If you have to take a stop along the way, keep your eye on the prize and don't lose sight of your goal. And from the employer side, treat people fairly. Remember that at one point in time in your life, whether recently, or a long time ago you were that candidate.
[00:42:55] Mosah: Yeah. One thing that people who haven't quite achieved their executive level status yet in their professions might be wondering is how long should I stay in a role? What does loyalty look like in the year 2022 and beyond? How should someone who wants to get to that level? But it's as a number of years, if not decades, before they get there, be thinking about issues of loyalty and their own management of their career.
[00:43:20] Matt: Okay, great question. I think loyalty matters. The loyalty can look different ways, right? So you can be loyal to a place and still leave after a year or two or three or whatever the time might be. I'm going to relate it to myself for a second. And then come back to the center of the question. I was a general four years.
That's not that long of a time in a lawyers lifespan very connected to the firm. I work with them. I'm friends with many of the lawyers there. I'm friends with many alumni there. It was an important part of my development. And a lot of that just depends on how you leave a place. And today's workforce is pretty mobile. People, you know, especially newer people coming into the, to the working world are willing to move more easily than, than people were a generation ago.
And as hiring people and executives, we have to understand that. And part of the success people are going to have is if I can make somebody better, they can find more growth, more success by moving on. But I'm part of that chain, right? I'm part of that. They're their success. That makes me feel excellent.
Just as good as people who stay in can promote all the way up. I don't want to stand in somebody's way. If I don't have vertical mobility for somebody, but they've got a great opportunity and I can help them get there and help them succeed, I want to do that. And I think most executives I know, and leaders and hiring managers, I know these days, feel the same.
This notion that you have to be loyal and stay until you're done working, or until somebody else leaves and you can take their job. That's unfair to people. Right back to that concept of you got to take care of yourself first. So I would be telling people, working their way up in their working life is you got to just pay attention to your reputation.
Right? And so if you're going to leave a place, because you think you have a better opportunity do it right. Be honest, be forthright with people, and then it's okay. If you're moving every six months, every year for no particular reason, other than maybe $10,000 more here or there every time, I think people will see through that.
But if you've got an opportunity to say I was there for a while, but then they hear, I had an opportunity to have a much bigger, let's take it in legal world. All of a sudden I was going to manage three different aspects of a legal function instead of just the one that I was doing here, where they were going to let me work internationally, or they're going to let me handle something else more directly.
That's a perfectly good reason to make a change. And I think people should be okay with that. On the flip side, there's also nothing wrong with somebody saying I really liked my job and I'm paid well, I like my boss. I like my colleagues. I like people who work for me. I don't have any upward mobility because I'm at the top unless somebody else leaves.
And so there's no upward mobility, but I like where I'm at. That's also a perfectly fine choice. So I guess the theme of all this for me is you got to make the choice that feels right to you. And then you gotta make sure you're treating people the right way, whatever that choice might be. If you're going to stay, obviously you're going to be a good team player.
If you're going to leave. Don't burn bridges. Don't be rude about it. Don't, don't do things the wrong way, because that is part of, now that is part of your story and you want it to be a positive part of your story. So I don't know if that answers your question completely, but I have people who've worked for me who are now at higher positions in other companies.
And I love that. That makes me feel like I'm succeeding. I'm doing something.
[00:46:24] Mosah: Matt on every episode, as I might've told you, when we were talking about you coming on the show, we support a different nonprofit for every guest. And I'd like to know today,what nonprofit you would like for us to support as a small token of appreciation for joining.
[00:46:40] Matt: Sure great way to close. Love the idea.
And when you raise this for me, which really quickly came to mind what I was going to want to do. It's actually not an organization that I'm directly involved with that I, when I see their work and it's really meaningful. An organization called Thresholds here in Chicago, they're very active in mental health and mental wellbeing community.
That's an important issue to me always has been it's of course become incredibly important and more in the spotlight through these COVID years, that's becoming more something that people are more comfortable talking about. I'm connected with them on social media. I see things they do in Chicago. I just think their work is so incredibly valuable.
And so my pleasant surprise for them, although we're not involved with them directly.
[00:47:23] Mosah: Thanks so much, Matt really appreciate it. Look forward to keeping in touch with you. Thanks so much.
[00:47:27] Matt: Thank you.
[00:47:30] Richard: Thank you for joining us on hiring insights. Remember, you can learn more about Top Talent Advocates and listen to other episodes by visiting toptalentadvocates.com and click on the podcast list
You can also email us at tta@toptalentadvocates.com.
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