How to Manage & Grow a Remote Team

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All right. Hello and welcome back. This is Colin Keely here, and I'm Brent Sanders. And we are two guys buying and building wonderful internet companies. Yes, indeed. And, we're starting to scale. So in this episode we wanted to talk about scaling people a little bit. So we're going, we've always had teammates, we've always had people helping us, but we're starting to get a little bit more of a solidified internal team.

We had some agencies working with us. We had. Contractors that were here and there, but as we've built up the team, one thing I wanted to talk about a little bit was like, what are the things that we're doing internally to, I don't know, what are the ceremonies? Like how do you manage these, these internal teams?

Now that I, I started putting that stuff on my calendar and doing them, I'm like, yeah, we should probably talk about this on the podcast. So I guess that was, that was the topic I wanted to kind of dive into first is like how we go about, at least on the engineering. How we go about doing that?

Yeah, I mean, I think at scale as we keep going, it's like, it's kind of a big game of recruiting. We just need more and more people to, fill seats. So I've had recruiting calls today, bringing more people on. It's exciting. It's exciting to like delegate more and not do it all ourselves quite as much.

But I guess, how's your life different now? Like, what are your, your, day-to. On the team side, it's not terribly different yet, but it's getting there. I keep telling my wife like, it's, it's, we're almost, we're getting there. We're getting there. She's like, why do you have to handle this? I'm like, cuz I'm the only one with the access.

So we're getting there, like, we don't have as senior support and, and I won't let everybody do, like direct access to production or database. Until we get certain controls in place and pay off some of the tech debt that we've kind of inherited in, in buying this, the latest business. It's like, I, I have to kind of keep things on a lock and key and I have to, to lead a lot of those things.

But that's the biggest change is like being able to step away, like. What Friday? I took my kid. I mean, it's been beautiful here in Cleveland. I don't know, you got the same weather right in Chicago. It was like just gorgeous last week. And kid, my son was on spring break. My, my daughter's, too young for school, but I, I took them on, on a Friday.

We had sort of a childcare snafu and I was like, you know what, I'm, take the day off. And the team kept things moving and that's like the biggest thing is like gaining leverage once again. Which, I, I achieved to a high degree in prior parts of my career. With Verne, we just haven't really been there yet.

So that, that's been nice to kind of alleviate the constant need to be pushing, initiatives forward and like, Hey, just trust the team. We'll, we'll be able to kind of take it. So you're much more like the, the team manager of the two of us. Like what's your process, what's your, team meetings one-on-ones, what's your go-to?

Yeah, I mean, I get, I think the first thing is care. Like to, give a shit. That's like the number one rule is. But yeah, start, one oh ones monthly. One oh ones is, is like step one. So we brought our first employee on full-time employee who's a, we've talked about for a local software apprentice, first software job out of, a prior job.

And then we have a, a couple other contributors and, and just kind of booking time with them one-on. To do a retrospective on the prior month, or in this case prior couple weeks. And so just simple format, what worked in the last month, what, what didn't, where do we have difficulties? What do we run into?

And then try to have like a, a single item to, to both walk away with, which is like, what's the one thing we can do better next cycle that we should focus on? And it may really be them or it may really be me, but we say it's together. So there's like, it's a little bit less blameless and passive, but it's not coaching, but it is to an extent.

It's an opportunity to just like provide candid feedback, which I think is, I don't know. I think there was a Ray Dalio quote, which is that people, most people prefer compliments, but accurate criticism is way more valuable, which is like, that's what I'm trying to deliver. Real things that happen and, and keep track of, it, it's not always super comfortable, but it, it's usually in the spirit of being constructive.

So that's, that's the first thing. Starting to do one-on-ones, which we did last week. And what yielded, here's the other thing that I should say to our listeners, and you know this because you didn't, we, neither one of it have done this. Like we didn't distribute a handbook like we're doing this still very startupy.

Aren't spending a month on, putting a handbook together. And we don't have an HR department. And I mean, we could have copied a handbook from someone else, I suppose, but we, we didn't distribute anything. So there's a ton of gray area, like I say, roughly nine to five, but if you need to take time off, like make it up, that's basically what I gave them and that, and an employment contract.

So it's , it's super vague. So this is where I, in, in my mind, we're able to , figure out what's working, what doesn't. So it's really a function of that more than, than, it's, what is the, the famous, the guy who says, management by abdication. It's a little bit of that and then coming back into kind of tune things.

Yeah. Mark Leonard says that Andrew Wilkinson says that Mark. I have some of that stuff built out in notion, I'm not sure anyone or other people look at notion nearly as much as I'm putting effort into it, like documenting sobs and stuff. But if you wanna look through it and add to it, we could use that stuff.

I have and, and I've put some stuff in there. I feel like we did a lot of that, like as I'm looking at it now, as I did a lot of that when we were onboarding the first folks. But yeah, you definitely have the line share of it in marketing and outbound and, but whenever I have like the key ones that I have, it's like how.

Test, how do we get reports from customers? How do we do stuff in Stripe? But yeah, that's, that's high leverage activity. So it, it's definitely worth working on. So that's like monthly, what do you do on like a weekly or daily approach with these people? Yeah. Daily, we have standups and that's, we don't do a standup meeting like, cuz those suck.

I don't know if you've ever gone through like a tech standup, but like yeah, as the team gets bigger, it's. There's always that one guy who's like lonely and wants to tell you about all about his weekend. And it's like, stop. Well, in theory is always like it's short, right? And you have to stand up. Yeah.

But in every startup I've been a part of in the past, it's never that people sit and just talk and talk and talk cuz there's no limit, right? Yeah. You're not forced to stand the whole time. So we do that asynchronously over Slack, especially we have other folks on time zones. What'd you do yesterday? What are you doing today?

Blockers and impediments. And then on a weekly basis this week, today we just started spinning up our weekly dev meeting. So structure here is, is fairly loose, but it's like something to kind of break the ice. I usually come up with some topic or it will tap somebody on the team to, to come up with a topic or a joke or something, but just get to know each other.

Cuz the thing that I'm struggling with is like, and I think everyone struggles with it, is like, Working on the same things. We have this connection, we're remote, we're working over Slack, and it's easy to forget. We're all human and it's easy to just be like, that person is assigned this and then they need to assign it to me, and the workflow goes.

So it's just like an hour to try to humanize everybody, and get them talking about where they live and the things they do, and the things they like. It's like all the shit that you would normally do. I hate to say the water cooler. We don't get to have lunch with each other. Right. Being remote. So it, it's kind of trying to replace that a bit.

I try to come in with some case studies or a case study at the very least of like something we did, something I've seen done or something else I've seen in tech related, like, employment of deployment of a certain technology or some technique that could work for something we're doing in one of our businesses.

So I like to, with junior teammates, have. Once you get that momentum going, show them how it's done, maybe two or three times, and then throw that responsibility around to the team and have them bring in sort of a show and tell of, Hey, I think this is cool. I think this is interesting. And that will shape, it builds the respect of like solution engineering across teammates.

Cause I think right now it's very, like we've got seniors and juniors and the juniors are the junior team member. I don't think he feels like he can be like, Hey, do this or we should do this. It's like he just feels like he's, I, he's gonna take. But we want to get him in the place where he feels comfortable throwing ideas out there.

And so that's like step one to doing that. And then, it's kind of like a longer standup format. What'd you do last week? What are you doing next week? Who do you need to coordinate with? And that's just great for visibility of, of everybody to know, like, how are we gonna work together in this next upcoming week?

And as well as like, how are the businesses doing? That's one thing I'm trying to, I would like to start doing on maybe even, outside of that meeting. Business wide r r growth, sh letting people know like, what's going on. And, what I would say is like, it's a great feeling when if things are like flat or even downwards and then you push something that you've been working on for a month and it, it starts floating up.

It's like that's, that's what I think everyone's kind of looking for from a how do I get charged by this work? At least I do. And I think a lot of the people on the. Jazz about that. And the money's the byproduct of that, your, your pay. But it's really like, Hey, this proves I'm good at what I'm doing, right?

This proves that like, I have value. This proves all these things to make me feel good. And if you're anything like me, you need that to, to keep doing this stuff, sadly. Yeah. Like you've looped in, connections to Slack. So a new customer signs up, their information is put in Slack. So that's like kind of ringing a bell of sorts.

Like if you're in a real office. We definitely are missing that like, big billboard that the sales team would be like, rah rah about. Yeah. I don't know if that's just opening up stripe to everyone in the company to like, Hey, you wanna look at how we're doing? Like this is how we're doing.

Yeah. But the other thing I think about is so we're a remote team. We're gonna continue to be, I mean, there's a little, contingent of you in Cleveland, but otherwise people are overseas and kind of all over. Like how do you build culture in that environ. We've seen other folks do a monthly or quarterly game night of sorts, like an online game night.

And we've talked about doing it. We've never done it. Any ideas around that. Yeah, I think we should do, like, I think we should just do that to start is like play a even like a silly game, like I feel like a clue or even like a video game, like, something simple, right? It doesn't have to be complex, but I.

Yeah, like I, I don't know. Past job we, we would play Call of Duty, like the creative director wanted to play Call of Duty with everybody and it just made everybody mad. Everyone would just get destroyed and get pissed off. But yeah, something easy, even like Euchre or something like that could be fun.

Like a team base game I think would be, I know it's a card game, but, encourage people to it. It's hard cuz it's like, the offshore guys, I, I don't feel like, I always feel guilty being like, yeah, you guys hop on our, our time, like late night. And that's like, yeah, that's when I'm supposed to be sleeping, dude.

I, I wanted, I've always had a very strong like, hey, work life boundary for employees and I've wanted to respect that, but there is an element of like, Hey, let's try to get together in a time that could potentially work for every. Even if it means like eating into your family time for an hour, I think it's, it is valuable.

We, we've been really bad at that, and, and it is. I think that's my one takeaway from this conversation is like, put, put some effort into that. Yeah. We've always had it like as it's due and other things just pop up and it kind of gets pushed away. I think it just has to go on the calendar and the way other startups have seen do it in the past is like, it's the end of the work day, so it's not eating into people's family time.

It's like from three to five or so. Instead of like five to seven. Yeah. So they're gonna be at work anyway. It's just like time off. Yeah. I guess we could do like a all sorts of fun things. I don't know. I, I think it would be fun to get in the habit of doing that and just building the culture a little bit more.

And for what it's worth, we do tend to have some like fractional help. And I think drawing them into those types of meetings as a priority is also helpful. It's like easy. It's like, Hey, we have some of your time per week, like let's say 20. But prioritizing that even more so with, with the folks that are fractional, just to make them feel like they're not like one foot in, one foot out that they are, I don't know, I think a lot of the micro SaaS folks have to rely on, on fractional help, right?

There's just not enough revenue to, to bring high quality talent in like senior talent in full-time for all their different roles. I think that's one cheat code you can use is like, Make it feel like it's fun and, and there's a connection and there's a reason other than like, yeah, I guess you pay part of my paycheck.

But if you have like whole, all of their sort of attention and energy and like they're behind you and they are rooting for you, then that's, I think you can get more out of that relationship. Yeah. I, I don't know what like the best online games are to play and maybe we both look into it, or, every week, every month, or every quarter, like it's one person's job to sort out what the activity.

And then it's always someone different. That's a good idea. I, I am, yeah. I am attracted to like, the most boring games, like simulations and stuff that's really technical and it, I should not be in charge. Maybe we can play like euchre even sounds hard because it's like, not a lot of people play it, but I know it's a fun team game.

Have you ever played a Euchre before the card game? No, I don't play any video games or card games. No, it's not, it's not a, a video game. It's like, A lot of people play it in college, like almost as a drinking game, but it's not necessarily, it's just, it's like a fun collective game in a, in a sense. It's, you play in pair in partners, so you'll have like a, a partner that's, you play with four people and I think you can play with more, but I don't know.

I, I'm not, I've played it a couple times and it's just been, everyone's having a lot of fun and, it's, it's like not too, Okay. Maybe that's it. Any other, team ideas otherwise onto, tech debt and features and stuff? No, no, I think that's, that's the main thing I think right now is, that's been what I've been up to in the last week, is just starting to pull the team back together and build some culture.

Cool. And so the other thing is like on Scout, say we've been pushing super hard on new features, moved from brain tree to Stripe, adding a bunch of stuff that's been like requested for years and like finally getting to it. But the other side of that is like, there's definitely tech debt and there's bugs and how do you think of balancing kind of those two, pushing on features and tech debt?

Yeah, I, I think of it as a see. Right, like it's, we pushed on the new feature Seesaw, like that side of it, and now we gotta come back. And so like we've had some pretty big known infrastructure things that, we just knew we're gonna have to deal with. But it's like you have to deal with all these things together.

It's kind of like financial debt, right? You can't go all in one way. You can't ignore your debt. You have to like pay it down in increments. Have like a good payment plan in place that's like sustainable. So it's, you have to strike that balance. I, again, I, I, I think it's tech debt and financial debt are very similar in this sense that it gets you some leverage, it gets you out ahead and, but yeah, you have to have something sustainable to, to pay it because now we have, people are happy, but you know, the, the bugs that have, when you kick up dust on a system that hasn't been touched in years or really.

Like the owner. Here's a, let's go give everybody the context we've talked about a little bit, but like, scout was built on Braintree. So he built this what, six years ago? It's six years old or eight years old. Cause there's some commits I see from like eight years ago, but I don't think it was really live then.

So it was built on one payment platform. We, we wanna move it to a new one because people hated the. He wanted to move and new customers just couldn't really get set up with credit cards. So we, we do that and it's like you have to touch everything. You have to touch all these old systems that, the first couple months of, of doing this was doing this project was like ensuring we could even like, touch these things and, and roll them out.

Like, so the bane of my existence has been not so much rolling the feature out, but just then the side effects of, we. 30 something or more branded applications. These are mobile applications that both have an iOS, an Android version. And if you're out there and you're technical, you know how painful it is.

If there's a bug in one of those, it's like you can't just push a change, it's gotta go through the app store. So this week I've, I think we're at a total of four expedited review requests. And it's not even a matter of of like, Hey, we, we tested this stuff and it's just a matter of. There are so many permutations in states that people can be in, and yep, we've definitely ruffled some feathers with customers, but I know that, they know I've gotten this across by directly responding and talking to these customers that like, we care.

We're on top of it. We're like doing everything we can, but in the long term, this stuff will go away and they will forget about it. And it's like, yes, this is painful. And yes, it's creating more time for them, which sucks. That's not what they're paying us for. They're paying us to automate all their, their operations.

So, it's a difficult thing. I think you can meet customers with kindness and understanding and empathy and just keep working and, and don't blow anything up. But yes, it's, it's gonna be bumpy and I think that's, That's just the case. And I think we're, we're still gonna see bumps as we go. We have some, the most dangerous stuff still ahead of us that we need to do.

The, the biggest tech that is forthcoming, such as like, it's gonna require some downtime, it's gonna require our maintenance period. So that's, that's in our future. I'd say the one thing we've done well is like, I mean, they knew these problems were outstanding. We said we were gonna tackle 'em.

We're like actively tackling them. And then we've just been over communi. So we send notices all the time. You record loom videos and then, something happens and we're on intercom and like there's always someone there to kind of help out. So that seems to help. It's just bumpy and not unexpected, I guess.

Yeah, no, I, I think this is as out of all the companies in our portfolio, this is the one that's probably, has the most surface area in the sense that there's two web applications there. Multiple microservices. There's, there's a ton of mobile apps that they run the same code, but still there's instances that you have to kind of come up with all these pipelines for.

And so we've done that work. But, when you have a, let's say you have a typo in something, which, not a lot of those things get up, but as a trivial example, you now have to push your pipeline. That pipeline has to build, it has to deploy, it has to go through review, it has to go. All the pain when you deal with mobile, which as, we dealt with this with avocado, was a total headache, and we knew it was gonna, this was gonna be the case.

So it's not a surprise. I think we're going, I think the history of this will go away. In my mind I'm concerned about loo, churn. It's like people getting pissed off. But I think the real effect is that new customers signing up are experiencing bumps and they are just like, I'm not into like, dealing with beta or even what seems like it's rocky and over the last week it, it's been like that.

So it's like, I think we're getting outta the woods o of the, the difficult stuff with changing billing providers. But in the long term, like, I know these are all things a we have to do. There's no way we could grow this business with, without these changes. And they've always been on a roadmap, but now it's just like the difficult period and.

It, it does fall all on me right now. Like that's, that's not lost on me. And there's a lot of pressure there, but at the same time, like this is, I know I can do it. I've done it before. And like, if it gets to the point where, how do I put this? Like, if it gets to the point where, this feels like it's out of my will or, or there's something that we can't do or I can't do.

It's like I know where to get help and I'm comfortable asking for it and getting it, and we have the resources for that. So it, but I, I think that's the, the end of it though. I think this is like the, we're kind of coming outta the woods on probably the most difficult change. We have a bunch of other changes, but the new features in front of us are just trivial in comparison.

We, we kind of swallowed the toad. Yeah, no, I think, we're starting to push on marketing more and I think there's a credible path to like five x this in a short, relatively short period of time. And if you take that mindset, it's like 80% of those customers are gonna be new. And what matters most is making sure those new customers are having like an amazing experience.

So this like bumpy road, I mean, obviously sucks for like the existing customers and for us. But it means these new customers are onboarding onto Stripe and like everything is just, should be in theory, much smoother going forward. Conversion rates should be better and like it's, it's all worth it. So as long as we're like, prioritizing the right thing.

Yeah, I think that's a great way of putting you, you mentioned that to me yesterday or Monday. You're like, we were kind, cuz everything that I have to deal with, How is this gonna impact new customers, but mainly how is this gonna impact existing customers and keeping them happy, especially our, our biggest customers.

But to your point, it's like they matter, but they're not everything. And in fact, if that, if our objective is, which it is to grow this five x, in a very, what I would say, compressed timeline, then we gotta, we gotta, we gotta crack some. I hate, hate to say it, that's all I've been thinking about.

Like people are upset that things are, are bumpy, but we gotta crack the eggs a little bit to, to make this, this growth omelet can't. You guys said that there's probably a better, metaphor for that. It's to make a a tolet. You gotta crack some greggs. Crack some greggs. Yeah. Yeah. I was thinking that.

I just didn't know if our audience was a success. Do you watch that by the, do you watch succession? Yeah, I love it. I, so I don't really watch TV or much of anything, but I do watch like the HBO premier shows for sure. You have the Sunday night routine. I had to stop watching cause it was, every episode was the same damn thing.

Is it gotten any better? Well if you didn't like it before, it's the same. So if you Oh no, I liked it. It's just repetitive. It's always trying to. Outsmart the dad and he's having a stroke or some sort of physical ailment and then he comes back and outsmarts all of them. Yeah, I mean that's the whole game, right?

It's succession in theory, is the idea. But it, the cool thing is that they said the end of the se end of the series is this season. So I always like that. Okay, you mode of storytelling of like, Hey, this is the end date, we're not gonna do this. String it on forever. Like house of Cards was good initially and just got super weird.

But succession is just like a well told story over four seasons or something like that. Yeah. I gotta admit like the best, it's hard to do because the money is there, but like if you remember the office, the the British office one season and they did one special, but it was just like one season and it was great.

It was just like, okay, that's it. We're done. It's like, it almost creates, it makes it better by not jumping the shark obviously. And, going, but I guess, one other thing I was gonna mention is, so on Twitter, if you have like a decent size account, you get pitched nonstop in the direct messages in the dms by like, fitness people.

Like we specialize in CEOs, we're gonna get CEOs in shape and, hey, do you need help on this column? So I get that like every. And I get other flavors of like, how best to monetize your Twitter account. And so I took a meeting with one of the, the companies yesterday. It's all about how to get like customers and clients, and I think a lot of what they do is coaching.

But I got an inside look at some of their economics and they have over a hundred clients and they've been adding like 20 new clients a month recently. And they charge $2,000 per. And so that's 200,000 plus in R and it's all recurring revenue. So I was just kind of blown away by how seemingly profitable these little agencies are.

And they basically train a bunch of other people to also be coaches, bring on clients, scale up courses, all different kinds of things like that. What would you say they. I think it's all about like crafting your positioning, your offer, trying to build a repeatable sales process, kind of built on top of Twitter, giving you scripts.

Mm-hmm. So I think everyone has different flavors, like they're working in different industries, but like the general approach is all the same of using Twitter to land clients. And seemingly they have a lot of case studies of people being successful. So I, I do think about like, if I wasn't me and someone else was running my Twitter account, like how would you best monetize that?

So we, we took a call of like, how do I get more acquisitions or like, find more investors and stuff like that, which was pretty far outside the wheelhouse. I thought they had some interesting ideas, but, It was all like updating the profile to kind of match and not focusing on, on growth as much, but really dialing in like conversion.

So dialing in conversion to like SaaS companies looking to sell and not like, just growing that follower number, whoever they may be. Right. This other, right. This other advice to me was like, put together a list of a hundred or a thousand people, like a hundred to a thousand people that I'd wanna meet.

Want to talk. And just like use DMS a lot more and like introduce myself and just start discussions, which is probably something I don't do enough. But yeah, it's just interesting advice overall. Hmm. Yeah, I mean I think, in the terms of like finding companies that want to sell or acquisitions as you put it, like that's super interesting in terms of investors.

Yeah. I, I think that like, whatever it is, is like continuing to connect with people. That's, that's the cool part. I, I think DMing people is, sorry, I, I'm, I'm an idiot. When it comes to you, they, they have to follow you for them, for you to DM them, right? Is that still a rule on Twitter? Mm, it depends on the person.

So if they have open dms, you could DM 'em, but then it ends up in like this other folder cuz they're. But yeah, that's something I've, so other people just have like an automation, Hey, you followed me, I'm gonna spam you, like, buy my course or whatever, use my service. Yeah. But like, I, I care a lot about reputation and the people that follow me, some of them are like billionaires, like legitimately big time people on Twitter.

And I'm not gonna say like, Hey, buy my like $200 course. I don't wanna burn any bridges. Like, I would never hand that over to a VA or something. So I'm sensitive to that kind of thing. It doesn't make as much. For me, as it does for like the other people selling services. Yeah, and I think the other thing is you don't wanna just be like, oh, I'd love to grab coffee or hop on a Zoom call for no reason.

Like I've, I've had a handful of those come through where it's like, like, I don't even know how to respond to you. Like I, I, I'm happy to give my time to strangers, especially that listen to this podcast, but if it's like, give me one compelling, like I, I got a lot going on. Like, I get, I get a very minimal amount of time before I, like, I have.

I have to go to home and I got to deal with two kids and, gotta do my thing. But yeah, that, that's the, the thing I've been getting more of is are the brain pickers and the, the coffee getters. Yeah. Those are tough because it's kind of like no one ever told them they shouldn't be asking to pick people's brains.

Yeah. I just, I did that to somebody once and he never responded. And I still remember and now I think about it, I'm like, oh, of course he didn't. I'm like, why would he, I was in college too. It's like some. Well if someone in college, I normally try to help, like I try to help students. Yeah. Cuz we were students at one point.

But everyone else, it's like, huh, you should maybe know better than to do this. Mm-hmm. Yeah. It's, and it's hard, hard to know, like, can I help? I mean, I think you, you do a good job of being like, Hey, check out the podcast. Let me know if you have like a specific question or something, or, but yeah, I always find it serendipitous.

It's like important. Connect random people. Whenever I do connect with people, I, nine times out of 10, I'm like, oh, I'm glad I, I'm really glad I took the time. This, I can feel like this, this will be worth it in some way, shape or form. Yeah. I only take the meetings where it's like, a founder that's obviously kind of a fit for us, or like someone doing something very similar where it's obviously we both benefit from knowing each other.

Everyone else, it's like, Hey, happy to continue talking here and if you wanna ask a question, like I'll try to. And then if I answer by text, I can repurpose it for like a tweet or something, um mm-hmm. But I basically say like, Hey, I'm not just gonna hop into a meeting with you. Yeah. It takes a lot of time and it's like the, the time before, the time after blah, blah, blah.

So yeah, it's tough to do. Yeah. That's all I got. Anything else you got? Cool? No, no. Excited to, excited to be kind of progressing on what we have in front of us. Excited. Get, get this team ramped up. I'm excited to have some leverage, which, will be fun to have again. Yes, I'll get you more help next couple days.

We'll bring on another person shortly here. Sounds good. Well, thanks for listening. All right. Take care.

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