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Josh Schachter:
Hello, everybody. Welcome to this episode of Unturned. It’s a very special episode for multiple reasons. I’ve got Jenny here, Jenny Calvert, my cohost with the Moe host, and I’ve used that on too many podcasts now. And we have a special guest, Waldman. , I don’t even know the name of your company. I don’t even know your title, but I know that I’ve played beer pong with you. I know that I’ve been to several conferences with you, that you know a ton about customer success, and that I wanna learn about your new role because this is the inaugural episode of talking to leaders, to, like, true leaders that have just joined new companies within the first hundred days.

Josh Schachter:
Right? We’re in our hundred day period here, you know, post election. So now we’re doing this podcast. And we want to, you know, really kinda showcase their background, like, give them a platform to talk about themselves as if, you know, to share with their whole company so that they their company learns about them, their customers learn about them, they can share their principles and philosophies, and also maybe talk a little bit about what it’s like, you know, coming into the new org and priorities for the the upcoming year, in this case, being towards the start of 2025. So with that long intro, Waldman, thank you so much for joining this episode.

Lawrence Waldman:
Thanks, Josh. It’s good to be back, and it’s good to see Jenny again today since we this is now our second time on Riverside.

Josh Schachter:
So you’re starting immediately with the plug of your own thing. Go ahead. Go for it. Go. Totally.

Lawrence Waldman:
Yeah. So I I don’t think actually it’s been posted yet, but it will be. And you I promise, Josh, we won’t be in competition.

Josh Schachter:
You’re you’re plugging a stealth you’re plugging a stealth project?

Lawrence Waldman:
Yeah. A little bit.

Josh Schachter:
Fuck you, . Come on.

Lawrence Waldman:
I Come on, man.

Josh Schachter:
If you’re gonna plug it, then plug it. Don’t tease it. Unplugging it

Lawrence Waldman:
as our success by stage that we do with our Almandari, and we we’ve already posted a few times. We even I think we did a little cross promotion when when you had the three of us on. Did. Okay.

Josh Schachter:
That’s so good. Okay. So you can plug it? Alright. Good. Good. Good. Good. Okay.

Lawrence Waldman:
These are all positive cross promotional plugs. Okay. And then

Josh Schachter:
you also have a podcast on music. Right? Is that right? And I

Lawrence Waldman:
I do. Oh, that would be great if I can get a little promotion for that. Yes. I I have a lot of fun.

Josh Schachter:
No pun intended.

Jenny Calvert:
‘s promo hour. Let’s let him get it all out. We wanna promote .

Lawrence Waldman:
Might as well get it all out. Yes. With two of my friends, we have a not video podcast, not a podcast on customer success, but one about music. I didn’t name it, but it is called Music Nerds Unite. And what we do is, every podcast, we go through a year chronologically, and we do a draft of what we think are the best songs of that year. We debate it. Sometimes we make fun of each other’s picks. We call these ones.

Lawrence Waldman:
And then occasionally, Spotify sends us a nasty note telling us that we’re not allowed to use the song. So because, god forbid, Metallica would, you know, lose out on a couple of pennies from the thirty second clip we use. So but, yes, I encourage you if you like music and if you like hearing debates about music, you should go check it out. Good memory, Josh. I I’m surprised you remember that.

Josh Schachter:
I listen to you. And in that podcast, , do you also fidget with something in the background that makes small little clicking sounds for your podcast? Okay. Just wanted to make sure that you’re consistent. Yes.

Lawrence Waldman:
I probably would

Jenny Calvert:
need to One more one more hot seat question. I’m going in. Alright. So if your if your new customer success org had a theme song, what would it be?

Lawrence Waldman:
Oh, wow. That’s that’s a great question. So I’ve I’ve used this before, but I think the best theme song that any customer success team could use is no surprises by Radiohead off of Okay Computer. Right? I mean, isn’t that what we all aspire for? No surprises. Right? You don’t want any churn surprises. You don’t want any organizational surprises. You don’t want any customer or product surprises. You wanna be able to execute your vision without having that.

Lawrence Waldman:
So that would be the theme song. Of course, it’s a little it’s a little dark, but just just focus on the no surprises part. Don’t focus on anything else.

Jenny Calvert:
, I’m going to I’m going to teleport

Josh Schachter:
to Long Island and rip that pen out of your hand. Thank you. Okay. Okay. Jenny, what would be your theme song?

Jenny Calvert:
My theme song?

Josh Schachter:
For your for well, you’re you’re you’re you’re with Update. You’re post sales with us here. You’re running the show. So what’s our post sales theme song for Update?

Jenny Calvert:
Can we create our own? That’s called LFC. Yes. K.

Josh Schachter:
I’ve already sworn in this episode, so let’s fucking see is

Jenny Calvert:
the Let’s fucking see. That’s our theme song.

Lawrence Waldman:
Okay. Not LFG?

Jenny Calvert:
Nope. See. Okay.

Lawrence Waldman:
Or no.

Jenny Calvert:
It’s intentional, but it’s not about us. It’s about you today, .

Josh Schachter:
Yeah. Mine would be mine would be mine would be no scrubs. I I don’t want no scrubs. That would be my team.

Jenny Calvert:
So That is totally spot on for you.

Josh Schachter:
Yes. Yeah. That’s only team players. Okay. Alright. We’ve gotten the banter out. You guys have done a very good job substituting for John and Christy in the banter aspect so far of this. Thank you for that.

Josh Schachter:
And so, , I actually really don’t know the name of your company. I really don’t know your title. And so I please tell us.

Lawrence Waldman:
That’s okay. I’m happy to. And part of that is because as Jenny knows, I I gave myself a a self imposed LinkedIn vacation where I intentionally didn’t go on LinkedIn for for probably about two and a half months other than very randomly. And I will tell you the name of the company and title, but let me tell you why. I feel as though whenever I go on LinkedIn, I see I see you, I see Jenny, I see Paul, I see Christy, I see a whole bunch of people whose ideas I really respect. But the way that the algorithm works, it consistently feeds me the same thing. And so I like it, I read it, I think about how it jives with my own philosophy about customer success and customer experience. And I started to wonder, am I making it so that I’m no longer having any original ideas? I’m only essentially synthesizing everyone else’s stuff.

Lawrence Waldman:
So I said, I’m gonna just stop. I’m not gonna look at it for a couple of months. And and it it actually turned I was it was supposed to be a month. It actually turned into a couple of months so that I could start thinking about things on my own or at least take a breath and start thinking about all the great information and great ideas that my colleagues and peers and friends have had and use that as a way to sort of rebuild what I’ve been thinking about and maybe even reexamine some of that. So Dan’s your Did you and did you enjoy it? I did. I did. Because what I I’ll get to it a little bit when you, you know, when we talk about what the first hundred days look like. So it did help me rethink some of the things that I’ve been thinking about within customer experience and customer success.

Lawrence Waldman:
It also was sort of a break because after a while, it almost becomes part of your job. Right? You feel compelled to either go on and put content out there, read content, and then figure out a way to take it and incorporate it into your own vision. And you’re you know, you read something, you’re like, that is so on point. I really wanna take this to my team. And then there’s another one and another one and another one. And after a while, it’s just overwhelming, and you start to lose the plot. So it definitely was worthwhile. I know I know you can’t see that.

Josh Schachter:
I, yeah, I hate LinkedIn. We Jenny and I were talking about it earlier this week. I was in Mexico last weekend on vacation, and, you know, I’m reading this new book on the beach, and it’s a a great book. And I’m learning all these things, and I’m taking notes. But, like, the entire time I’m reading, I’m I’m writing in the margins, oh, this is a LinkedIn post. Oh, this could be the first line of my hook hook post from this from this chapter. It’s like, just freaking enjoy yourself. You know? So Yeah.

Josh Schachter:
I don’t I don’t have Instagram. I don’t have Facebook. I don’t know this. I I just, I have LinkedIn, and LinkedIn is my social media. And I’ve tried currently, it’s on my my mobile phone. I have the app. But, actually, usually, I don’t have the

Lawrence Waldman:
app off your mobile phone at one point.

Josh Schachter:
I did. I did for, like, a year, and it’s it’s on now, but I need to remove it, but it’s bad. Okay. Anyway, so there’s yeah. Oh, yeah. So where do you work? What do you do?

Lawrence Waldman:
Alright. So so I work for a company called GLMx. GLMx is a SaaS company in the capital market space. And what we do is we have software that helps traders in very specific markets. It automates and makes it significantly easier for them to be able to engage with one another. And it is in a space that for many, many years was not technology averse, but was very, very rudimentary in how they would engage with one another. So you would have two traders who wanted to work together. They might message each other on Bloomberg and negotiate back and forth.

Josh Schachter:
Same company or no? They’re different buy side?

Lawrence Waldman:
Two different companies. So one on the buy side, one on the sell side.

Josh Schachter:
Yeah. Okay.

Lawrence Waldman:
And they might do that and to be able to engage. It’s time consuming. It’s not efficient, and you don’t have the ability to be able to scale. Our software gives you all of those things. It’s extremely efficient. It makes it so that you can do multiple things and work with multiple counterparties at the same time. Yeah. And it we are regulated, so you do have the security of knowing that you are able to trade effectively, efficiently, and be able to really improve your execution.

Josh Schachter:
So So it’s g l n x m. Okay, Mary. Markets. Okay. Because g l n x goes to site not found, so I’m glad that it’s the m and not the n.

Lawrence Waldman:
Yes. And you’ll be glad to know I I lifted my LinkedIn hiatus, and now I even updated.

Josh Schachter:
For me, I do appreciate that.

Lawrence Waldman:
And I

Jenny Calvert:
do Josh.

Josh Schachter:
Yeah.

Lawrence Waldman:
Yeah. Exactly. And for other people too, but mostly for you, Josh.

Josh Schachter:
Thank you.

Lawrence Waldman:
And so I was brought in

Jenny Calvert:
So so wait.

Josh Schachter:
So you are you I mean, like, big, what do they say? Big, hairy, audacious goal? Is it to to disrupt Bloomberg?

Lawrence Waldman:
No. No. Not at all. It’s, it’s it’s to bring efficiency and transparency to a specific part of the market.

Josh Schachter:
Okay. Cool. So yeah. So you were brought in.

Lawrence Waldman:
So I was brought in to lead our customer experience team. Our customer experience team are the ones who help optimize our users’ and and clients’ use of the system. They act as expert level support, and we do proactive engagement as well. So it is a mix of a lot of different things. The reason that GLMx asked me to work with them is that we are very much in a growth mode right now, and we are scaling. We’ve been around for a long time, but we are really, really picking up momentum and scale. And a lot of the things that we used to do, although extremely effective, aren’t necessarily gonna translate as we continue to grow. So

Josh Schachter:
So where where are you in the life cycle, the the the company life cycle now? Start up, not start up?

Lawrence Waldman:
Like right? I would say we’re in scale up mode.

Josh Schachter:
Scale up. Okay.

Lawrence Waldman:
Cool. Yeah. Exactly. And so we have had I mean, it’s an award winning team that I’m fortunate enough to be able to join and lead. A lot of that, though, is due to the amazing work that the team does, but not necessarily because we’re able to scale that. Right? Like, we have really, really knowledgeable, tenured individuals who work really hard to make sure we give our customers an amazing experience, and it is extremely gratifying. Like, I will see messages from clients to our team literally every day saying things like, you don’t understand how much our lives are better since we started working with GL Next because we’ve made them that much more effective and efficient. Right? We’ve reduced time.

Lawrence Waldman:
We reduced inefficiencies. And yet when we continue to grow and add more and more clients, that same level of experience, we’re not gonna be able to do if we continue doing things the way that we are doing now, which is not bad. It’s it’s great. It’s just not scalable.

Josh Schachter:
Yeah. I have a whole bunch of questions that I’ve written down in advance, but, Jenny, I don’t wanna just sit here and spit ball, spit fire, rapid fire, whatever questions at . So what do you got for ?

Jenny Calvert:
I think I’m hearing a lot of, like, change management and transformation, right, especially, like, them bringing you in. So what what is it in your in your past experiences and the work you’ve done in customer success that gets you, like, the most excited to do this work moving forward? Like, what does that look like?

Lawrence Waldman:
Yeah. That’s that’s it’s a great question because it’s one that I ask myself whenever I think about potentially making a change or joining a new place. And if I was to capture it in two different components, the things that I love the most are I love working with a team where I know the team is really good. It’s really knowledgeable. They really understand our platform, and they really understand our clients and what that connection between the two is. They also may not necessarily feel as though the rest of the organization understands that and even in some cases recognizes that. So being able to take that team, which we which I know has far better knowledge in our clients and our workflow and our platform than I will have or certainly when I start out, and may not necessarily have some of that recognition about how they themselves fit into the overall structure of the company and help elevate them through process, through inspiration, through leadership, through structure, and sometimes through innovation. Those are the things that I gravitate to.

Lawrence Waldman:
Those are the things that I really love. And I don’t think I realized that earlier on in my career or when I would take on some new roles. But then when you do it once or twice, you really start to recognize, like, that that’s your either your superpower or at least what helps drive you. I mean, I take this might sound crazy because I have to wake up we we’re in the capital markets. We start pretty early. So I have to wake up pretty early in the morning. But I do wake up in the morning pretty energized because I know the team does great work, and I know it’s only the tip of the iceberg. I know we are going to continue to do great work, and we have so many things ahead of us to be able to make that more efficient and more effective that it’s it’s almost overwhelming in a positive way to think about how much we can get done if we have the right focus and we can have the bandwidth to be able to do so.

Josh Schachter:
How long have you been working there now? We’re we’re filming this just for because we’re gonna release this probably a little bit couple weeks, but so it’s February 7 right now. So how how many So this week

Lawrence Waldman:
this is four months. I joined in October.

Josh Schachter:
Four months. Okay. Alright. So well, so you don’t really qualify for our first hundred days, but that’s okay. We’re making You know what?

Lawrence Waldman:
If we if we actually did the days, it was the October. I think we’re really close.

Josh Schachter:
We’re really close. Yeah.

Lawrence Waldman:
I wanna say we’re we’re we’re, you know Yeah. More kind of error.

Josh Schachter:
Okay. Cool. Alright. So, so a couple things. There are a lot of people that are looking for work, sadly. Right? It’s getting better. It’s still not good. I actually, in particular, know, well, which makes sense because it’s like a pyramid, like, of opportunities.

Josh Schachter:
I know a lot of folks that are are at your level, maybe, you know, just slightly less less tenure, and that’s really tough to find a job. Right? Because, obviously, there’s less opportunities when you’re talking about director, VP, CCO, etcetera. How’d you get this one? Now clearly, you have the, like, the perfect background because your background is all in, like, financial service SaaS, right, for, like, however many years. But but, practically, what was your process of getting this job? Because I I know there’s a lot of folks out there that are listening that don’t have a job or looking

Lawrence Waldman:
to switch. Yeah. I I was fortunate. I had started working when I left my previous job, I really did wanna change. I wanted to look at something that maybe was not financial services. I’ve been doing it for a while. I took a mini break and went right back into it, and I was looking for opportunities that might have taken me outside of that. But I also have to recognize, as you said, in this kind of market, you can have every qualification to lead a team, But there are a lot of people who do that and who also have market or workflow experience.

Lawrence Waldman:
Right? So you can’t it’s very hard to be able to switch unless you either have great connection with somebody who who knows what you can do and is willing to not I don’t wanna say overlook because that’s not really the right word.

Josh Schachter:
Take a bet.

Lawrence Waldman:
Willing to say, you know, hey. Look. I I trust your experience in customer facing roles, and that is more important to me than having market or workflow expertise.

Josh Schachter:
Yep.

Lawrence Waldman:
So in this case, I had been working with somebody who was encouraging me to look at other things. And one day, he called me up and said, look. I I know I know you said this isn’t really what you wanna do anymore or what you you know, you’re thinking making a change, but this is a really great opportunity. I really think it matches. At least talk to these these guys and see see what you can, you know, find out. Yeah. So I did, and I really, really hit it off with the leadership team, but I also recognized, again, those two things that were compelling to me. Great team, experienced team, need some help to understand the vision of what customer experience and customer success, customer support can be, and we are at a growth mode where we really need to be able to develop the process and structure so that we can grow and scale and still maintain the same level of exceptional experience that we have right now.

Lawrence Waldman:
You know, the more and more I I learn, the more I realized, okay, a, this is a great opportunity. B, even if my experience is related or not, the other parts of the job that I really like, this is gonna give me those two opportunities. And at the time, I was talking to a couple of other firms that were either in adjacent or slightly different spaces. And one of them in particular, I felt this sounds this sounds so disingenuous because I know, as you said, there are a lot of people who are looking for roles. I almost felt as though I would have been bored. It was a great team, really experienced, been in SaaS for a long time. They had a good leader. The leaders went on to go, you know, to move to another role.

Lawrence Waldman:
And I would I suggested a whole bunch of things that I would wanna do, and they’re like, yeah. We we do that, or we have a team that does that, or we we’ve already done that. And I I even asked at one point, okay. So what what do

Josh Schachter:
you need me for? They’re like, well, we need you to

Lawrence Waldman:
figure out what we’re doing. And I’m I thought, that sounds great. And maybe that wouldn’t be so bad at some point, but I don’t know if I would be as excited about that as, Pam about this opportunity.

Josh Schachter:
So what excites you if you think back to your first one hundred days that you’re now rounding out? What were I’m gonna combine two things. What were your top priorities in those months slash excited you the most?

Lawrence Waldman:
So the top priorities were I think whenever you join a new team, there’s there’s always a, like, a hidden priority. It’s not gonna be in your, you know, six thirty, sixty, ninety day plan. You may not even articulate it. But one of it is just, how does this company work? Right? What is the what’s the culture? How do I navigate the company? Who do I need to know? Who do I need to engage with that isn’t necessarily in the org chart or isn’t necessarily something that you would learn as part of your onboarding? Companies just have their own way, and you need to learn that. So I’ve always tried to make that a priority, and, fortunately, we are we are small. It’s not it wasn’t super difficult to be able to do that because I had a I have a great team and a great bunch of people that I work with. So they made that part easy, but it’s still something that you need to focus on whenever you join a new company. Yeah.

Lawrence Waldman:
Second, of course, is where is the team now, and what is their appetite for change? Are they open? Are they willing to change? Do they even see the need to change? And, again

Josh Schachter:
How do you assess that?

Lawrence Waldman:
I think you have to assess it. It’s it’s one of these things where it would be great if you could assess it from a quantitative perspective. Right? But you know you can’t. You have to the only way you can really do that is by having conversations, throwing a few ideas out here and there, suggesting some things that, you know, you very well may know you want to do, but you don’t necessarily want to impose it on the team. It’s more about, let’s talk about it. Let’s get some buy in as we go, and then it will organically become a team goal as opposed to a meeting goal. Right? A new guy coming in and saying we should or should not do this. That’s always how I’ve tried to operate.

Lawrence Waldman:
And I, again, don’t want people to think, especially my team because I am very transparent with them, that this is, like, some nefarious plot. That’s just the way I I try to do things. Right? I suggest. I talk. I ask for feedback. And it starts to change from we’re gonna do this because this new person came in and said we should do this to we’re gonna do this because we as a team think this is the right thing that we should do. And that helps with both change management, but it also helps because one thing I tell my team whenever I join, whether it’s I’m leading a team of directors, managers, you know, a 200 person organization, or a small team of 10 individual contributors, I’m gonna tell you a lot of things about what I think we should do. If at some point you hear me say something or you hear me make a suggestion and your immediate reaction is, wow.

Lawrence Waldman:
That is literally the stupidest thing I’ve ever heard. That may be great at some other place, but that is not gonna work here. Fantastic. Tell me that. Tell me that in a in an open way. Tell me that with the idea that you will explain why you think it’s not a good idea and what you would do differently, and then we can move on. As opposed to, I tell you this is what I’d like to do. You have that same inner monologue.

Lawrence Waldman:
That’s a really dumb idea. You do it anyway. And then afterwards, when it doesn’t work out, you kinda give me a, well, I told you. I you know, I never

Josh Schachter:
told you

Lawrence Waldman:
that I was thinking of an idea. I told you so. Or even worse, you leave, and then you talk to Jenny and say, Jenny, can you believe you said that? That’s, like, that’s seriously one of the stupidest ideas I’ve ever heard. Well, I can’t believe we’re gonna go down this road. Right? I would much rather you tell me. I don’t have ego in that.

Josh Schachter:
So, Jenny, Jenny, I I wanna jump over to you now on this because, you you’re you’re also a professional coach, executive coach, you know, leadership coach, and a really, really, really, really good one. And

Jenny Calvert:
so,

Josh Schachter:
you you’ve got somebody like who comes in, and, you know, he’s he’s got years under his belt. I’m not calling you old, , but you’re slightly. And, he’s he he’s led, he’s led teams I mean, you’ve led teams of, like you’ve led, like, a 200 person team in the past. Right? And you you got these amazing logos and all this kind of stuff. And so you’re like, yeah. Anything goes. Tell me whatever’s on your mind. 27 year old, like, you know, three years of experience CSM.

Josh Schachter:
Bullshit. Bullshit. Like, you’re intimidating right now. You’re not actually intimidating. But, like, that that to somebody that’s that’s that’s at this what you guys are, like, what? Like, sixty, fifty, 60, 70 people at the company? Fingers scale? Yeah.

Lawrence Waldman:
Yeah. Yeah. We’re we’re under a hundred. Yeah.

Josh Schachter:
Okay. So, like, so that like, how do you actually Jenny, the question technically for you. How does create this genuine environment? I know that his intentions are there. How does he actually create that environment where, his team is not afraid to speak up and to to push back and to to jostle in, you know, in in good ways?

Jenny Calvert:
Yeah. Love it. I think what I’m what I’m hearing from that’s awesome is you’re creating buy in, and buy in facilitates and brokers trust. And trust you know, different people build trust in different ways. But if you say something, something happens and you come through as promised. Right? That that sets the foundational elements of trust. And so early, you can come in, give your entire monologue about how it’s gonna be different. You want people to tell, , that’s a stupid idea.

Jenny Calvert:
You know they’re not going to say, , that’s a stupid idea at Josh’s point. What I think is interesting is you’ve created the environment and held the conversations to have one on one dialogue to learn what’s going well, what’s not going well, what should we start basically, start, stop, continue is what I heard. You didn’t say it, but some kind of exercise like that to open up the dialogue. Start, stop, continue?

Josh Schachter:
Never heard of it, actually. I I’m not being facetious.

Jenny Calvert:
Seriously? It’s fun.

Lawrence Waldman:
You’re No.

Josh Schachter:
I’m I’m swear to god.

Lawrence Waldman:
What should we what should we what do we do right you you essentially assess all your process or lack of process. And so what should we continue to do? What should we keep? What should we do that we currently don’t do? So that’s the start. And then stop. What are the things that we know are just not good that we need to stop doing? The I and Jenny and I have talked about this before. The stop is always the hardest because, particularly in customer success, a lot of the stop are things that the reason why you’re doing it is because nobody else is doing it. And if you stop doing it, that basically means no one will do it, which means most of the time, it’s the customer that suffers. And I had you know, everything is not always amazing, but I did have a stop start continue esque conversation with my team just yesterday where we even said, look, we know we shouldn’t be doing this. No.

Josh Schachter:
What is this? What is this? Yeah. Well Let’s let’s put

Lawrence Waldman:
it this way. It’s a it’s a common go to market SaaS company problem, right, where something falls in between, which means it usually falls to the client experience, client success team. And the team has said, we know we’re not supposed to do this. However, if we don’t, the other team is not going to, and our clients are gonna suffer. So, basically, you know, the the ask was, we need you to fix it. And my response was, yes. I’ve already identified that as something we need to fix. However, we have to do a few other things first.

Lawrence Waldman:
And if we wanna get this done and if we wanna be able to make a compelling case, we have to make a compelling case. And the way you make a compelling case at any SaaS company is you quantify it, you figure out what the return on investment is, and you come up with a solution. Because if you miss any one of those three, you’re usually not gonna be able to be successful. Yeah.

Jenny Calvert:
How do you how do you stay on top of all the promises that you’re making early? Like, I hear a lot like, even this example. Right? Like, we’ve got other things to do first. We’ll get to it. How do you make sure I I as a leader, I’ve had things that I’ve said that about May fall off because other things come up. How do you follow through?

Lawrence Waldman:
Yeah. That’s that’s a that’s a great question. And I think whether this is your intent or not, it’s very much related to the question that Josh asked you, right, which is how do you build that trust? Because, yes, if I say, you you guys are totally right. That’s something that we need to work on. And now I’ve done 10 things where I’ve agreed and said, yes. We need to work on them, and I come through on one, well, I’m probably not gonna have a lot of trust. So the way I do it is I do when I first start, try to come up with a nascent thirty, sixty, ninety day plan. I’ve always sort of been a little skeptical of them because they’re kind of unrealistic, and I’ve always found that many times people forget about them.

Lawrence Waldman:
Like, they don’t you don’t really get held accountable for them because it’s still your first ninety days or a hundred days. Maybe we should change it to a thirty three, sixty six, and a hundred day, Josh. Maybe you could start that trend. So I use that, though, as a way of sort of outlining projects. And the way that I’ve done it here and I’ve done this in the past, but I feel I feel like I’ve done a better job here. As I’ve said, these are our first priorities, and these are also gonna be part of our OKRs as a team. These are our secondary priorities, meaning we know we wanna do this. But if I say we’re gonna do it now, we’re not gonna be able to do any of them.

Lawrence Waldman:
So we’re not gonna do them. We’re just know we just know. And then these are the wish list ones. These are the ones that we would like to do, but I’m not gonna promise we’re gonna do them. And I’m not going to even commit that we’re gonna look into doing them until at least that first group, the ones that I say we’re gonna do and are part of our OKRs are gonna be done. Where where do

Josh Schachter:
you memorialize those and communicate those?

Lawrence Waldman:
I knew you were gonna ask me that.

Josh Schachter:
So Because because, like, I want real golden nuggets that somebody listening to this podcast is like.

Jenny Calvert:
Just like when you’re grooming the product backlog, Josh.

Josh Schachter:
So you have

Jenny Calvert:
Notion. I don’t know.

Lawrence Waldman:
Yeah. So no.

Jenny Calvert:
We do. Do you? No.

Lawrence Waldman:
No. We do not have Notion. And I was gonna I was gonna admit, I have tried using lots of different tools to be able to do this, and I always find they work for a little while and then they don’t. And that partially, the reason they don’t is because it’s hard to maintain. So this is gonna be He’s

Josh Schachter:
going to Post its, by the way. This is where this is leading. Yeah.

Lawrence Waldman:
I am. No. I I actually I put them into PowerPoint, and the reason I did that was because it made it easier to consume. Then I translated them into OKRs. We have a system that uses our OKRs, and I put them in. But I’ll tell you right now, like, the OKR system that we have is really bad at doing a couple of things. It’s it’s great for posting OKRs. It’s really bad at measuring OKRs.

Josh Schachter:
Mhmm. You know what?

Lawrence Waldman:
I realized I just I said that and, like, you know, folks in my company are all listening. I go,

Josh Schachter:
I can’t

Lawrence Waldman:
believe you just trashed one of our things.

Jenny Calvert:
Opportunity for improvement. Put it on the thirty three sixty six one hundred day plan.

Josh Schachter:
Yeah. Exactly.

Lawrence Waldman:
But there there probably is something out there that does a really good job of measuring all these things and tracking them. I just I just haven’t found it yet. I’ve seen people do it in Google Sheets and Excel too. Right? Just another way of doing it. So

Josh Schachter:
So, I wanna talk about some of the surprises you encountered in your first couple months. And I have a feeling if I ask you a pleasant surprise, you’re gonna tell me your team, which leader wouldn’t. But you’ve already inferred that. So is it your team? If yes, then let’s move to the the bad surprises.

Lawrence Waldman:
I’ll give you I’ll give you two pleasant surprises.

Josh Schachter:
Okay.

Lawrence Waldman:
One pleasant surprise one, yes, team. And but but I I always feel like saying that is is unintentionally pejorative. Like, it’s not like I thought the team wasn’t gonna be good, and I was pleasantly surprised that they’re awesome. I kind of just I I assumed that they were gonna be amazing, and they are. And and that also sounds like hyperbole. Like, of course, any any, you know, person coming in thinks their team is awesome or hopefully thinks their team is awesome. But Jenny’s shaking her head already. Yeah.

Jenny Calvert:
I walked into a situation where the team was not awesome, and I knew they were not awesome. And the first thing I had to do is figure out where they go. So

Josh Schachter:
Okay. That that Don’t talk about it today like that.

Lawrence Waldman:
I’ve been I’ve been lucky.

Jenny Calvert:
Fired, Josh. Fired.

Lawrence Waldman:
Yeah. I’ve been very fortunate that that is not the case, and it’s certainly not the case here. I am I was surprised by how deep some of the relationships that we have with our clients are. And I’ll I’ll give you a few

Josh Schachter:
I love that.

Lawrence Waldman:
And and the reason again, I I don’t know why I was surprised. I think I might have been jaded a little bit from previous experiences. But there is a very, very unique way that we engage with our clients. And so we are, many times, speaking with them multiple times a day and week. And we just happen to have a client event, and I’ve been to client events before. There you can tell the vibe. Right? Sometimes the vibe is, I’m just coming here for free booze. Sometimes the vibe is, I’m coming here because I wanna see something or I wanna say something.

Lawrence Waldman:
And sometimes the vibe is, I’m coming here because I really feel like I wanna meet some of the people I engage with all the time in person, or I wanna see them again. And that was the vibe that we had at our recent client event. Again, like, I I tease my team about this, but it’s true. They some of them were literally treated like rock stars. They were like, oh my god. I can’t believe it’s you. Like, I’m so glad to meet you in person. Clients saying this to the team.

Lawrence Waldman:
It was really, really gratifying. So I I again, I don’t wanna say I was surprised, but it was just fantastic to say. So now you’re gonna ask me the negative Wait.

Jenny Calvert:
Wait. Jenny, I think you and

Josh Schachter:
I had that experience when we first met. Right? Because you were a customer of UpdateAI, and then we first met. Was it it wasn’t where was it not a problem?

Jenny Calvert:
Was that the CCO workshop in San Francisco?

Josh Schachter:
Oh, that’s right.

Jenny Calvert:
That’s the first time we met in person.

Josh Schachter:
And were you already a customer or not? I mean, you might not have been.

Jenny Calvert:
Yeah.

Josh Schachter:
I feel like we had that moment.

Jenny Calvert:
Yeah. Yeah. That you did. Because I I mean, it’s

Lawrence Waldman:
like super excited to see Jenny because she’s a rock star?

Josh Schachter:
She was super excited

Lawrence Waldman:
to see me. Oh,

Jenny Calvert:
yeah. Of course.

Lawrence Waldman:
Yeah. Yeah. Of course.

Josh Schachter:
We’re vibing. We always vibe. Yeah. So what what’s the what’s the tummy rumbles? What’s the tummy rumbles that you that you didn’t expect?

Lawrence Waldman:
So the thing that I didn’t expect is we we have, as I said, a great engagement strategy with our clients. It really works well. It’s definitely not scalable, and we’re working on that, but it really works well. The thing the thing that I was a little surprised about is I would sometimes ask, and still do, members of my team, how do you manage this? Like, how do you do this? And the answer is usually, we just do. And, of course, my response is, okay. But what happens if you aren’t here and we now have you’re now leading a team of five people who don’t have it? How are we gonna do that? And the response is something along the lines of, well, I’ll show them. And the great the great part about those conversations is as we’re having that conversation, you the realization starts to dawn. Okay.

Lawrence Waldman:
No. That you’re right. That’s not gonna work. And so the part that’s surprising is we do have these exceptional relationships, as I’ve said, and yet there are things that I know and the team knows and the company knows. We need to be doing differently and better because we have to have more structure and more process to it, and we can’t rely on the fact that we have great individuals doing extraordinary things, that’s not gonna scale. And the I guess another part of that surprises is the way that they do it without having some of the tools and technology that, you know, we might think are fairly commonplace is pretty impressive. Right? So those are some of the priorities that we have as we are moving away from that. We are adding more process.

Lawrence Waldman:
We are adding more tools to their so that they can engage even more effectively. So it’s it’s a good problem to have because if the company was resistant, which they’re certainly not. I mean, it’s part of the reason why they asked me to join. That would be one thing. But the fact that they recognize it and we just have to execute on it, that’s that’s a that’s a good place to be.

Josh Schachter:
Sounds sounds like a great decision to join. Sounds like, I I get the vibe that it’s yeah.

Lawrence Waldman:
It really was. I mean, I I actually I came home late because of an event that we had yesterday, and my wife, Kenina, asked me, like, so, you know, how’s it going? I said, you know, it’s really going amazing. Like, I I don’t have days where I think to myself, oh god. This is a really rough day. I I think to myself most of the time, this is a great day. It could have been better because I wish I had gotten this done, but it was still a pretty great day. And if you can have those more days than not, you’ve made the right decision. I have them almost every single day, which is pretty awesome.

Lawrence Waldman:
I am I tired at the end of the week? Yeah. But it’s a good tired, and it’s the it’s the I’m tired because I know we accomplished stuff, and we still have a lot to do, which is awesome.

Jenny Calvert:
Yeah. Not the I’m tired because I have 87 unread Slack messages from Josh tired. Right?

Lawrence Waldman:
No. Because we don’t have Slack. We have Google we have Google Chat. But I do there are times when I get overwhelmed. I mean, one of the things that we do is we there’s a lot of work that we do that has an email that goes to the entire team, which may you know, which we are working to make more efficient. But, yes, there can be days when I will step away and come back to hundred emails. Not everyone that I necessarily need to action, but probably has some information that is going to help me in my own journey learning more about the team and our clients and what we do. So, yes, that could be overwhelming.

Jenny Calvert:
When do you think your learning journey ends? Like, when when when does your, like we’re we’re in the first hundred days, like, part.

Josh Schachter:
Because you know that the answer that you’re looking for is never. It’s a continuous lifelong cycle.

Jenny Calvert:
No. But, like, when do you shift out of, okay, you have the phases of joining a new organization, you’re stepping into this role, you’re identifying the priorities, you’re setting the OKRs, the targets, you get to know the people. Like, when do you move from learning phase to truly executing and and running the show? Like, when does that shift happen for you?

Lawrence Waldman:
I I would say that so that happened relatively quickly.

Jenny Calvert:
Yeah.

Lawrence Waldman:
But they’re not distinct phases. They’re parallel. So, yes, Josh is right. The learning phase is never gonna end, particularly because there are specific things that I need to know about our clients and about our workflow that I just don’t know. So that will never change. And this is a pretty dynamic but rapidly changing part of the capital markets because there are some changes coming from a regulatory perspective and from a process perspective, but also because there are huge swaths of the market that are not digitized or, you know, or electronic trading yet. So that part’s never gonna end for me, or at least it won’t end until, yeah, I’ve quite some time. But the execution, we we are starting to execute on a lot of the plans that we have.

Lawrence Waldman:
And you guys know it’s the same thing. Right? When you’re when you’re at a smaller company, a start up or a scale up, execution can be exciting because it’s easier to execute change when you have a smaller company. Right? If you have a 5,000 person company, change is harder because it’s you have to get through so many different hurdles and approvals to get something done. Some of the stuff that we do, my team says, hey. Can we do this? And I do it, and it’s ready in five minutes. Right? That’s great. It also means that we are doing and executing a lot of this on our own, meaning me and my team. Right? We don’t have a support team to be able to help us.

Lawrence Waldman:
We don’t have an operations team to help us. Right? We don’t have some of the things that you might have at bigger companies. It’s us, which means that the team, in addition to their day job, which is long, they might be on multiple different teams for projects that we need to do to continue to build out our client experience motion. And that’s a lot because, again, we don’t have somebody who’s just gonna go, okay. I’ve took taken all your feedback. Here’s what we’re gonna do now. You guys just tell me if it’s gonna work. No.

Lawrence Waldman:
They’re building it, testing it, executing it, iterating it, while still doing their day job at the same time. So it’s a lot, and I’m grateful that they’re so accepting of that and and doing it so effectively.

Jenny Calvert:
, gonna leave it at that. Thank you so much. Congratulations on

Josh Schachter:
the new role. Sounds like

Lawrence Waldman:
you got

Josh Schachter:
your company, great fit, great opportunity. And, yeah, I’d love to have you back on, and we’ll see, you know, later in the year maybe how those priorities are are going,

Lawrence Waldman:
how things have evolved. I’m looking forward to that, and I will not play with anything as I’m talking.

Josh Schachter:
Oh, that’s okay. That’s okay. That’s, you know, I I know.

Jenny Calvert:
Schedule it when, like, the Florida sun is not hitting my face all the time?

Josh Schachter:
We didn’t notice that.

Jenny Calvert:
You didn’t? Like, the little glimmer glow?

Josh Schachter:
No. You’re good.

Jenny Calvert:
You’re good. I I noticed it.

Lawrence Waldman:
A little bit. Okay. Do you before we close out, do we, do we want to put any bets on the game? Well, we won’t be in trouble if we didn’t put

Josh Schachter:
bets on KC with our Kansas City

Lawrence Waldman:
I’ll put

Josh Schachter:
it here.

Lawrence Waldman:
There’s no way that I would be rooting for the Eagles.

Jenny Calvert:
Really?

Lawrence Waldman:
No. No. A, unfortunately for me, I’m a Giants fan. And, b, I have lots of friends who are Eagles fans, and I don’t want them to be gloating. I wanna make fun of them on Sunday night.

Josh Schachter:
Yeah. It’ll be Casey. It’ll be Casey.

Jenny Calvert:
K.

Josh Schachter:
Alright, guys. Thank you so much.

Lawrence Waldman:
Alright. Thanks, guys.