Customer Support Leaders

275: Unlocking the Power of Fractional Leadership in Customer Support; with Brian Levine

Charlotte Ward

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Ever wondered how startups can access top-tier leadership without bringing on full-time executives? Brian Levine, joins me to share his journey and unpacks the innovative concept of fractional leadership in customer support. 

Brian has been in tech support, in one capacity or another, for 15 years. He's been VP of Support at GitHub and Head of Support at Plaid, among others. These days he's the co-founder of Yetto, a help desk for modern support teams. Brian lives in Rome and drinks far too much coffee.

From his experiences at those industry giants like GitHub and Plaid to founding his own help desk company, Brian reveals how part-time expert guidance can be a game-changer for startups. Discover how companies can skillfully manage transitions and foster a robust support culture with the expertise of seasoned leaders even when they're not ready for a full-time role.
 
 Curious about the impact of fractional leadership on early-stage companies? We tackle strategies for startups lacking a dedicated support head, where initial consulting can highlight system gaps and pave the way for longer-term partnerships. Brian discusses how identifying potential failures in support processes can compel businesses to seek further expert involvement, ultimately helping them scale successfully. Whether you're exploring support leadership careers or intrigued by the challenges and triumphs of being a founder in this space, this episode is packed with insights that promise both inspiration and actionable advice for navigating the dynamic world of customer support.

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Charlotte Ward:

Hello and welcome to episode 275 of the Customer Support Leaders podcast. I'm Charlotte Ward Today. Welcome Brian Levine talking about fractional leadership.

Charlotte Ward:

I'd like to welcome to the podcast today for the very first time a special person who I've met at many a conference and finally pleased to have pinned down to come and join me for a conversation. That person is brian levine.

Charlotte Ward:

Nice to have you, brian, nice to see you hello, hello good to be here finally after all these years.

Charlotte Ward:

Yeah after all these years it's been a. It's been a long time that we've been circling in the same environs, hasn't it?

Brian Levine:

yeah, I've been in. I've been avoiding you, I've been avoiding you, it's I, I mean, I got that impression, it's nerve-wracking, you know yeah yeah on this podcast and, and the longer it goes on, the harder it is to say oh, I would love to be on there. You can't. You know, five years down the road anymore right yeah, do it.

Charlotte Ward:

I get the sense that like I'm now like a circling kind of bird of prey in the support community or something I'm gonna get you all you'll get us, you'll get us, yeah there's just no excuses anymore, is there? Um, yeah, well, um, I know who you are, but would you like to introduce yourself for the benefit of our listeners?

Brian Levine:

sure, yeah, I'm brian, I uh I'm the ceo of, uh yetto, a little help desk, uh, that we're we're building. Uh we're just in beta now, so most of you might not have heard of it, but you will very soon. Previously, I've been the VP support head of support, et cetera, et cetera, for folks like GitHub and Plaid and Abstract and Meter, and now I'm building my own thing because I got sick of using other people's help desks.

Charlotte Ward:

I feel like we were all a bit sick of using other people's help help desks. I feel like we were all a bit sick of using other people's help desks, so I'm excited to see another one, yeah, it's the dream. It's living the dream to get the thing to do. What, exactly what?

Brian Levine:

you wanted to do exactly, exactly yeah, yeah, yeah, awesome.

Charlotte Ward:

Well, thank you for joining me now. You touched on you're a founder at the moment, but you touched on something there that you've had all of these other roles and today we're talking to that a little bit, aren't we? We're talking about roles in other organizations, so not not a founder of a help this company. That I'm sure, um, you can come back and talk about that anytime, but another time, another time we're talking about leadership, and we're talking particularly about fractional leadership. Right, yeah, should we begin with a definition. What does fractional leadership actually?

Brian Levine:

mean oh man, that is such a good question. Um, there, I've actually done this in a few different ways. Um, where I've come in as like a head of support for a company and worked like part-time, like they don't they're small, they have a small team, they might not need a full-time head of support, but they need some help. So I've come in as, like you know, one or two days a week doing head of support work, running a team and hiring. But I've also done sort of interim support work where I've been their interim head of support for, you know, a few weeks or a few months while they hire a full-time person or while they're in some sort of transition state between folks or during a reorg, things like that. So there are a couple of ways to do that and the work is very similar across them but the needs are kind of different yeah, yeah, yeah, I can see that.

Charlotte Ward:

So. So with the uh, with the sort of ongoing fractional work in that sense where you might be head of support for a startup two days a week, I can see how that would be really beneficial for the startup that wants somebody more experienced than a first support hire might be to lead the function and like actually build out the uh, the processes and the culture around what it means to deliver support. But maybe isn't necessarily doing particularly for technical products, say, doesn't have the experience or doesn't have the technical knowledge right exactly right.

Brian Levine:

So a role like that you're often coming in and you're you're like partnering with the person who's there, maybe not? Uh, maybe they have like a team lead or you know someone at like a manager level or like a very experienced support person, and you're there to kind of fill in the gaps for them, right?

Brian Levine:

like I've I've been at other places. I've been doing this for 10 years, so I've seen a lot of things that work and that definitely don't work. And you know if they've got some specific problems, they're like, oh, we could use someone who's seen this thing before you come in and like maybe train us up or get us through this you know phase for a little while. That's been super fun.

Charlotte Ward:

I can see that would be and implementing all of the things that we with, with the level of experience that you and I bring to this role, all of those, all of all of those things like getting a good help desk in place. I'm going to leave people to fill in the gaps on that. By the way, yeah, I'm going to remain agnostic, but but yeah, it's.

Brian Levine:

It's like getting the tools in place, helping folks like figure out a process for things. Uh, as my, my favorite one is actually when, when a company is like expanding their product line in some way and they're like, oh, we don't know we have to change, like who we're supporting and how we're supporting them, and like we don't really know how to make that transition, we don't know how it works and how you split up a team and coming in and helping them through that, uh is usually uh, pretty fun, because watching people do that poorly is is so painful.

Brian Levine:

right, you're like, oh, I've seen that go. Well, I know you could do this, but like you don't quite know what you're doing and like it sucks to watch someone screw that up. Uh, so being able to like jump in and help out, even if it's just you know a couple hours a week to to answer questions is is I?

Charlotte Ward:

don't know, it's really like gratifying on on my end to like be able to do that for folks, and it's a bit meta, isn't it? Because, as support people, we like fixing things. Yeah, and then, and then, what's better for a support person than fixing things in support right?

Brian Levine:

it really is.

Charlotte Ward:

It's like the ultimate support work, right I know, I know it's so good and I I. It just puts me in mind of like the way you were describing, like watching people do things badly, and how kind of I sit rocking in my chair sometimes just wanting to kind of get in there and do it with them or for them. You know, oh, it's so bad I have that reputation in my domestic situation as well, where I'm just like just I.

Charlotte Ward:

I just just exactly that there. You summed it up in one one phrase. That's basically just let me do it just let me do it or give me that. I think that's the other thing. Give me that thing, like just give me that.

Brian Levine:

I say that all the time just just give me that I'll do that. You go do that other thing, that other thing still needs doing, and I can just get this working.

Charlotte Ward:

And when I've done this, then I'll come over there and help you do that.

Brian Levine:

Right. So imagine being able to do that professionally, like that's just, it's great, it's living the dream.

Charlotte Ward:

So when you're, when you're in a role like that say, say, you're doing two days a week do you do? Do you run these kind of roles concurrently, so you're in one place there two days, another place, place, or does that? Is that too much of a like, like a? I'm trying, I'm gonna try and use some nice language now.

Brian Levine:

Does that mess with your head too much yeah, do we have to use nice language here? We?

Brian Levine:

know we don't yeah yeah it, it really does. Uh, it's really hard for me to do that. It is. It is very difficult. Uh, I get and this is like a personal flaw, and I know a lot of people in support are like this, so people listening to this will be like, oh, that's me, that's me. Uh, working two days a week is a scam, right? You're always going to be thinking about that problem. The other, you know, five days there's no weekend in your brain, right? You're thinking about this problem all the time. And it's great to have these two days where, like, you're basically on call or you're having meetings or you're like working with the team, but those other days, like it's still kind of ruminating, it's it's still mixing back there so I've tried running some of these concurrently like overlapping, like I'm wrapping one up and I'm starting a new one, and financially that's great right.

Brian Levine:

Keeping work going is wonderful, uh. But mentally the load of that is has been too much for me, so I tend to not do that I tend to. If I'm doing like a fractional uh fractional like head of support type work or a consultant work like that, I'll do something else in the other time, like I'll take on other types of projects or other uh side gigs to fill in the gaps, because having two things that are similar uh tend to just like crowd the brain, I think.

Charlotte Ward:

So it's a fair point. I love, by the way, just briefly, the the phrase there's no weekend in your brain. I know exactly. I know exactly what you mean. I have another one which I use, which is that support never sleeps. Um and uh, yeah, 24 seven, isn't it? It really is.

Brian Levine:

With this kind of work, you're always supporting the support team, right? And if it's a full-time leadership role, a consulting role, a fractional role, your head is always in it and you're always worried about the people and the team and their customers. And yeah, having two teams to worry about simultaneously, uh, that's when it gets stressful for me. So I I can't do that that makes sense um this.

Charlotte Ward:

I'm just curious. This personal curiosity, what?

Charlotte Ward:

do you?

Charlotte Ward:

do. That's so different from support that you can. It can coexist happily in your brain, say, the other three days of the week um.

Brian Levine:

Prior to getting into support, I was an engineer um so I do. I do like development work on the side also nice, nice.

Charlotte Ward:

That's completely different headspace, isn't it? Yeah?

Brian Levine:

it. It is, I mean it's, it's absorbing, uh in, like the problem solving aspect of it is satisfying in the same way, but it's less people driven and I don't have to worry about you know, I don't know the the support leadership. You're worried about customers, you're worried about the business, you're worried about the people these people's livelihoods are at stake like it feels, um, like very personal on a bunch of different levels, and when you're, when you're writing code, when you're just like making some software work, it doesn't feel quite as personal. It's it's a fun puzzle, but it doesn't, uh, yeah, it doesn't trigger the anxiety in the same way yeah, yeah, it's not.

Charlotte Ward:

It's not as reactive. Yeah, actually, I think that's the biggest driver, isn't it?

Brian Levine:

of the tensions is the reactivity in any support team yeah and it's just it will never go away, that's just the job, right, that's how it is.

Brian Levine:

And when you're doing this, uh, this fractional work, you say you know I tell people like oh, monday, tuesday, wednesday, like those are my days, like I'm on call like nine to five. It's never nine to five. But you tell people like you're on call these hours, uh, and you really are on call, like people will jump into slack or they'll text you or whatever with like problems, large and small, all the time, and you're basically on retainer so you're there to to help, uh, and you just can't put it away right. And when you're working on a different type of project you know non-reactive work you actually like kind of control your own time in a different way.

Charlotte Ward:

Yeah, yeah, yeah, yeah. That um, that being on call is, uh, it's, it's, it's hard to uh, it's hard, it's just, it's just hard to put it down. It's just hard to put it down. That that bit of me that says give me that thing at home, it's just it's hard to put down. It's really yeah, um, so, um, I guess, I guess just to bring us back to kind of this as a sort of profession sorry, I didn't mean to say sort of profession as a profession, absolutely a sort of profession.

Charlotte Ward:

Uh, it feels like a sort of profession, yeah as fractional leadership, as a professional mode, let's say, um, how do you find these roles? Because I in my experience, organizations don't advertise for fractional they had, for they advertise for the role right yeah, uh, it's such a weird time right now too.

Brian Levine:

The past year or two uh things have maybe more than a year or two, maybe the past four years, things have like shifted. A lot there's been this is going to get into like industry stuff too right, there's been like a lot of layoffs for a lot of reasons and people are trimming down teams and uh, like one of the reasons people hire like interim or fractional roles is because they, you know, they've let go of their team and they think this is like a cheaper way to do it. So there's like I don't know they're.

Brian Levine:

The different. Reasons for people to bring on a fractional or interim role or a consultant role vary and that means the way they find people to fill those roles kind of varies. Uh, for, for, like, very early stage companies who don't have a head of support, don't really know what they're doing. They want someone to come in and just show them the ropes and get them started. They often do advertise or someone on the team support driven is a great place.

Brian Levine:

Someone will pop in and be like can I get help with blah, blah, blah? And once you see someone asking for help for a couple of weeks in a row, uh, you'd be like do you need like a little, a little more help with that? So that's, that's actually worked for me a couple of times, um, but most commonly, uh, because I've been in support leadership for a long time, at this point, uh, folks reach out to me like folks I've worked with at github or plaid or now abstract, when they're their next place, uh, you know, and their team is looking for help. They they know that I do this and so I get you know, I'll get a message.

Brian Levine:

Right, someone who was at plaid uh, not even in support, I think it was uh, someone like the hr team at plaid took a new job somewhere else and then then they were like oh, we're looking for, uh, an interim, like part-time uh seat. Are you available to just come in and like, help us through that? Uh, but my favorite way to do this like by far is folks who are not looking for the role who are, who are just looking for some, for some advice, uh, so the way I usually get the here's.

Brian Levine:

Here's some job advice for anyone looking to do this right. Uh, don't try to fill the seat of the, the head of the fractional head of support, the consultant, whatever. Try to, you know, give some offer. I, I think you know, a couple years ago I was telling folks it's like uh, for for $5,000, I will come in and I'll talk to you and your team, uh, and it's like a two week project and I'll just look at everything you're doing and talk to some customers and give you like a summary of what I would do differently.

Brian Levine:

What I've seen works, what I think you should change, what you should go, uh, you know, harder on which we should double down on, uh, and then I'll, I'll, I'll tell you like how to implement those things. So you don't, you don't have to hire me to do the work. Uh, it's just like five thousand bucks to give some advice. Uh, and almost every time they say thanks, that's great. Uh, this has been, you know, a great report. We're going to go implement all this fantastic. And I say you're probably not going to go implement it.

Brian Levine:

Here are my rates for coming in and doing this like as part-time say. You're probably not going to go implement it. Here are my rates for coming in and doing this, like as part-time projects for, you know, one month, three months, six months, whatever it is, and they said great, we don't need that, we're going to implement it. And almost every single time, three months later, they come back and say they haven't done any of it. How much would it cost for you to come in and fill that role? Uh, because they weren't looking to fill a fractional uh, you know, head of cx role, they weren't looking for a part-time project consultant. But after seeing where their gaps really were. They were like oh, we actually, we actually need this yeah, you convinced them convinced.

Brian Levine:

Yeah, it's a little it feels a little sneaky after you do it a few times, but like it works out for everyone, like they really do need the help. I'm never like scamming people. Like a lot of a lot of companies don't especially like really early stage tech companies don't know how support works right.

Brian Levine:

They have this vision of how they think it works and they know their customers super well, uh, but there's this gap that they don't even know exists, until someone starts to point that out for them and like once you've been doing this while I'm sure you know, you've seen, like how things break as they scale up.

Charlotte Ward:

So it's very easy to predict, isn't it? Yeah it, when it's. When it's when it's three engineers in a, in a you know broom cupboard somewhere, um, and they're supporting five customers, that's doable. But suddenly, when that becomes a little, even a tiny little bit, successful, it's three engineers trying to develop something, but with 20 customers or 50 customers asking for help, suddenly it's a different ballgame.

Brian Levine:

Right and you can look at what they're doing and be like here are the three ways that's not going to work And're like, oh, we got it, we got it. I'm like, okay, I think you might have it like there's a good chance, now that you see those gaps, that you could fix it. But if you can't like, just give me a call yeah, and that's you know that that kept me employed for many years that's awesome.

Charlotte Ward:

That's awesome, uh, and and you know, as you say, it's not a scam like they need the help. So, yeah, and there are multiple ways to solve it, right? I mean, actually it might make sense for some of those organizations to say you know what brian's? Brian's given us a 17 page report here.

Brian Levine:

We definitely need someone full-time, but super early stage very definitely almost might not need someone full-time yeah, yeah yeah, yeah, some of the some of the jobs I've gotten have been like can you just come in and help us find the full-time person? Like that's the job, right, uh, which is which is great. Like I'm not a great recruiter, but I know the work. And like there are a lot of people uh in the support community who can do that. Uh, looking for full-time work, yeah just helping them, helping them connect to the community, has been great yeah, absolutely, absolutely, um.

Charlotte Ward:

So we talked a little bit about the the fractional, let's just touch on. You started this conversation um saying that the two were quite different the the interim role. Um, let's just touch briefly on the interim and how that's different from from fractional because, it's a venn diagram, I suppose, isn't it? There is some overlap between but, but interim tends to have an end state in mind, whereas fractional doesn't necessarily, I guess yeah uh, I do like the interim roles.

Brian Levine:

Uh, I think a little bit more. Uh, because of that end state, you have like some specific things you're trying to achieve. You know it's going to be. You know it's usually like six months, right.

Brian Levine:

Because, the, the, the end state of that is they, they do fill that role with a permanent person or they do promote someone internally. So getting like everything set up, getting the tools set up, getting the process set up, often hiring, uh, when you're doing the, the interim role, uh, as like full-time for six months, you work with hr or the talent acquisition team and you, you try to build a team around, uh, you know the work that needs to be done and around the person who they're bringing in and me and again, like maybe fill that like vp or head of seat and help like that recruiting.

Brian Levine:

That's super fun.

Charlotte Ward:

Uh, I've really enjoyed doing that yeah, yeah, but team building like the act of building a team is is really quite good fun, isn't it? Yeah, yeah, it is uh, yeah, and it's.

Brian Levine:

And there's something like oddly sad about doing that and then walking away. Right like you, you spent like six months like getting this team set up and bringing in the leader, and then you maybe have like a month transition time with the new head of support, where you're just there to like back them up and they're in charge. You hand everything off and then you say goodbye to this team that you've just spent six months like training up and and you work with, like the leadership team to like get everything organized across the company and then you're peace.

Brian Levine:

Like that was fun. I'm out, uh that's.

Charlotte Ward:

That's been rough. I mean that, uh, that sounds like those people who foster puppies who are then going to go on and be like. It's exactly like that right, and you know they're going on to better and greater things.

Charlotte Ward:

Yeah.

Charlotte Ward:

But you've helped them.

Charlotte Ward:

You can't be part of it.

Charlotte Ward:

You can't be part of it. Yeah, yeah, that's so funny, yeah, no, I can see that, I can understand that.

Brian Levine:

And a couple of times this has happened twice now where, like I'm halfway months in or I'm four months in and the CEO or whoever it is that I'm working with will say why don't, why don't you just come in and fill that role? Uh, and sometimes it's really tempting right like you're doing this because, like you, you like working with the team, you like building that team. But also part of the fun of doing this, like as a sort of profession uh, is the bouncing around and solving different problems over and over, instead of getting caught up like working with one company. You know, I was at GitHub for like five years and going through like the phases of that and all the different issues that come up over time, like that's super fun, uh, but in a different way Uh.

Brian Levine:

So when I was in this like sort of uh, interim fract, fractional, like consultant mode, I didn't want to get caught up in like a single company for years on end, uh. So, yeah, like a little bittersweet to like turn that down yeah, yeah, no, I can understand why.

Charlotte Ward:

But yeah, I mean, every role eventually comes to a point where you think i've've got everything I can out of this and this is a well-oiled machine and it needs a new person to take it on to the next stage. Or, you know, grow from the, you know the system that you've put in place, or you know and adjust it going forward. But yeah, yeah, you need to. We need, we need problems to solve. We support people, for goodness sake.

Brian Levine:

I yeah, I originally got into doing this kind of work because the problems weren't bad enough at the company is I kept getting jobs at Like I needed like a really ugly mess to sort through and that I like that is so much fun. Like the messier it is is the more fun it is to fix I couldn't agree more.

Charlotte Ward:

I couldn't agree more. Uh, yeah, yeah, yeah, uh. Brian, thank you so much for joining me today. It's been an absolute pleasure to learn a bit more about this profession it's sort of a job.

Brian Levine:

It's sort of a profession.

Charlotte Ward:

I mean, I didn't say job, at least I'm a professional, it is a job. It is a job, it is a sort of sort of profession.

Brian Levine:

It's a sort of career and for anyone listening to this who's thinking about getting into this, like I highly recommend it, like if, if getting into that, like deep problem solving uh thing seems appealing like this, this is it, this is this is super fun yeah, yeah, you certainly made it sound it and uh, and thank you so much for uh an entertaining and informative conversation.

Charlotte Ward:

So, uh, will you come back and talk a bit more about uh being a founder in the support space another time?

Brian Levine:

yeah, I would love to awesome.

Charlotte Ward:

thank you, so I'll talk to you soon.

Charlotte Ward:

That's it for today. Go to customersupportleaderscom forward, slash 275 for the show notes and I'll see you next time.