219: Building a Team from Scratch with Kat Olsheske

Charlotte Ward: 0:13

Hello and welcome to episode two hundred and nineteen of the Customer Support Leaders Podcast. I'm Charlotte Ward. The theme for this week is building a team from scratch. So stay tuned for five leaders talking about that very topic. I'd like to welcome to the podcast today, Kat Olszewski. Kat, it's lovely to have you join me for the first time. First of all, for the benefit of our listeners, would you like to introduce yourself?

Kat Olsheske: 0:45

Of course. Hey Charlotte. Thank you for having me. My name is Kat Olshewski. I am the Senior Manager of Support for Open Path Security. I've been a customer support person, manager, leader, lifer. So happy to be here.

Charlotte Ward: 1:06

Thanks so much for joining me. And this week we are talking about a topic which you suggested to me. And I'm ashamed to say I had never thought of this as a topic for the podcast before, but I do think it's a great one. And I think it's actually one that a lot of people encounter at some point. And certainly in startup land, we see this all the time. The topic for this week is starting a team from scratch. And I'm really interested to explore over the next 10 minutes or so your experiences in this area. Like it let it like really any specific challenges you've found and uh and maybe even finish with like a top tip or something. So let's see if we let's see if we can go through that whole journey in 10 minutes. So let's do it. So where do we where do we begin starting a team from scratch?

Kat Olsheske: 1:58

Yeah, so I mean I brought this up. Uh I've seen the chatter, you know, and in support communities talking about this. And I myself have gone through this. Well, this is my second time now. Um, prior to OpenPath, I was uh customer support manager for Formstack. Um when I started there, we uh had uh a team of five, and by the time I left, you know, um I had a pretty decent sized team. I had um a big tier one group, tier two, I had a couple team leads under me. Um so we've grown quite a bit, and I was there for about three and a half years, you know. Um, and then now here at OpenPath, um the company is still fairly new. So we launched in 2018, and you know, it's the same thing, right? Like I have a team of six currently, and um our business is going through some growth and our customer base is increasing, and now we're at a point where we need to start to scale and really, you know, build uh a team, a support team from you know, startup to enterprise. So yeah, uh, you know, and we have a lot of startups also um out there, so it would be good to share some of that experience. So uh all of the other support leaders uh kind of know where to start.

Charlotte Ward: 3:31

Yeah, yeah. So you've done it twice. What what was the um what's the first challenge? What's the first thing you think of when you when you think about those those two experiences? What have they got in common in those early days?

Kat Olsheske: 3:46

Um, well, I think the the most I mean the one thing that I have in common is is kind of the knowledge portion. Uh it the type of knowledge is different, but uh the first go I had uh it was the first time I've had to, you know, scale a team, build a team up. And from there, um, you know, because before that, my teams were already well established. So this was the first time that I've had to build up a team. Thankfully, I've I had a really good leader um that that worked with me and you know guided me and taught me, you know, all the things and gave me some really good feedback. Um, so I I really appreciated that. And in this role, um, also knowledge because I'm not quite familiar with the industry. The industry is new to me. So, you know, that growing a team, you also need to understand your customers and the industry that you're in because you grow it differently based on the different needs of the customers and and the different uh you know types of of the company. So knowledge, but just a different type of knowledge.

Charlotte Ward: 5:06

That that's a really interesting observation, actually, that uh how you grow the team depends really on your customer base and the type of customers you're serving.

Kat Olsheske: 5:14

Right, exactly. Because every customer, you know, every customer base has different needs and every business operates differently. So the type of team you've built for one company and the type of structure might not work for a different company, right? For another company. And, you know, that's kind of what I'm experiencing here, where there are some things which, you know, uh like backbone of support where you build some really um good behaviors, start with some like a vision, a mission, you know, uh your DNA basically of support that's that carries on no matter what industry it's in. It's just the process is is different based on that.

Charlotte Ward: 5:58

Yeah, yeah, I would agree with you. And I think that that um that DNA that you talk about is really it it's both very generic in the sense that there I think are some really core principles to good support that you can carry from organization to organization to organization, whether you're starting that team or whether you're taking on a slightly more established team. Um, but they're also quite personal as well, aren't they? I think every leader, like as they step into particularly these really small organizations, forming the team utterly from scratch or really early days, you you've got quite a personal way of doing things as well, I think. Right.

Kat Olsheske: 6:42

Yeah, exactly. And and even with that, you you also still need to match based on the type of customers you work with, right? Because I mean, the general principle of it is the same, wherein you know, you in order to be the best, you gotta, you know, you have to have structure to be the best. But what is it? Like um, one company might be more focused on small businesses, whereas another company is more enterprise focused. So their level of best might be different because of the different types of you know, support that they offer based on their customers. So essentially the same, but again, slightly different. It's kind of like uh having a twin, not all twins, you know, are the same.

Charlotte Ward: 7:34

Very true, very true. And and it really does change the shape of the work, doesn't it? The the type of organization that you're involved with, but the people that you're at those organizations that you're dealing with as well, whether you're dealing obviously, we all know we can draw very a very definite line between B2C and B2B, but then are you talking to analysts or engineers or end users or and that really changes the behaviors of your support team as well.

Kat Olsheske: 8:03

Right, exactly. Yeah. And that's also where one of, I guess uh my me personally, one of the pain points, right? I mean, not just knowledge of the industry and knowledge of growing a team in general, but also finding that right structure that um aligns not just with the team, but also with the customers, right? How like if you let's say you want your customers to be able to reach out to you through chat, then you have to look at internally, okay, as a team, are we able to support chat? So you got to find a good balance of you know what you can comfortably offer to your customers, um, and know that internally you also get buy-in from your team that they're comfortable with what you're offering.

Charlotte Ward: 8:54

Yeah, yeah. And and one thing that I think is really key in the early days is is finding the right balance between, particularly when it comes to challenge channels, between what you offer and the appropriateness of what you could offer. Because frankly, you could do quite a lot, but but you don't want to overstretch yourself. And I think that's another challenge early on. I think is it's finding where that line is. You want to go so far because you want to, you really want to help your customers and and like maximize that value, but but you can only do so much in the early days as well.

Kat Olsheske: 9:32

Right, right. And what I'm noticing too is, I mean, of course, when you're in a startup environment, you know, everybody does everything, right? You you're the jack of all trades, you do everything, you wear all the different hats, and your customer base is so small that you're able to give them more attention, and you know, uh, and which is great, but how do you scale that, right? So that um I've I've seen it where customers like, oh, you used to offer this, and then now not anymore because you guys have gotten so big. And it's like, you know, how do you grow so that you don't ever get to a point where you were better before when you were smaller? Now that you're big, you know, you you don't care anymore. So whatever you do while your business is small should be something you can continue to do as you get bigger.

Charlotte Ward: 10:25

Yeah, yeah. If you do it too haphazardly, it uh taking stuff away from customers is always painful. Has to be done. I mean, some sometimes it just has to happen, but you have to as part of I often say as part of putting on the big boy pants. Yes, you know, yeah, as as part of growing up a little bit organizationally, you might have to streamline and and redefine. But and that can involve, you know, recontracting or redefining services which might not be entirely um subjectively beneficial from your customer's perspective, but it's the only way you can get to the next place, isn't it?

Kat Olsheske: 11:07

Right, absolutely, especially in support where you know support in general is not a revenue generating uh team. So, you know, you're expected to deliver a lot, and oftentimes you don't necessarily have the resources to deliver what's expected. So a lot of support leaders are faced with the task of you know making their lean team look like a giant team, right? Like you have a team of five internally, but externally that has to look like you are a team of 50. Yeah, right. How do you do that? Yeah, yeah.

Charlotte Ward: 11:43

Well, I I don't know if that that's where you're leading us towards as as we close out this this chat, but um I you did promise me like one top tip. It's it is I did. Is it is it is it how you make five people look by 50, or have you got something else that we should be?

Kat Olsheske: 12:01

Oh I I'm still looking for the secret assass for that. I think I got it, but I'm not quite ready to share. But um, you know, for those who are in a startup, the my best tip would be to plan ahead, right? Like uh create a five-year plan if you can, and ensure that in at the end of that five years, you know, it's a clear goal of what you know, what's the finish line look like? And then from there, figure out, okay, how do I get from start to finish and ensure that once you cross the finish line, it's a goal that you can continue to sustain and grow. Because you don't want to get to the finish line and then say, okay, the race is over.

Charlotte Ward: 12:48

What's next? So good planning. Um, five five years is ambitious in startup land, but um, I think we can aspire to that because I think I really like the idea of like you have that vision. And if you have that vision, I think everything that you do, every step you take towards that vision is always and only ever going to lead you to behave and operate in all of the ways that you need to behave and operate in support anyway, which is with efficiency, with growth in mind, with you know, an eye on the right tooling and the right people and and and everything else that we we all know makes good support happen, right?

Kat Olsheske: 13:29

Right, absolutely. Plus, you can see, you know, you can map out what you need to do and what you can deliver in that time. It does sound like a long time, but in startup, you know, like I said, you get to a point where you offer too much too soon. And then once you grow, you're unable to scale it. But if you look at it five years in advance, you can spread that out. So you don't get to a point where, you know, oh my, now we've grown so much, we can't deliver the same level of excellence now. You know, you can't you can spread it out through that five years.

Charlotte Ward: 14:04

Yeah, that makes a lot of sense. Thank you so much, Kat. Thank you. That's it for today. Go to customersupportleaders.com forward slash two one nine for the show notes, and I'll see you next time.