Latest / Pre-Sales Pathways / Brian Mazzaferri, Global Head of Solutions Consulting at Rippling

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Brian Mazzaferri, Global Head of Solutions Consulting at Rippling · Pre-Sales Pathways

• Chris: Hello and welcome to Presales Pathways, the podcast that showcases highly successful pre-sales professionals and the different career paths they've taken. I'm your host Chris Clark, and on today's episode I'm joined by Brian Mazaferi, Global Head of Solutions Consulting at Rippling. Now, whilst many SaaS companies have been struggling, Rippling has been on an absolute tear, recently passing the 1 billion ARR mark, which represents a staggering 78% year-on-year growth. And Brian's own career has been on a similar trajectory, going from senior manager to VP of Solutions Consulting in a little over two years. For anyone that's thinking about moving into management or potentially going from first line to second line leadership, Brian has some amazing advice to share in this episode. So let's get into it. Hey Brian, good to see you. Thanks for coming on Brian Mazzaferri: Hey Chris. Chris: the show. Brian Mazzaferri: Good to see you too. Happy to be here. Chris: Yeah, this is the inaugural episode of someone covering a leadership role as well, rather than an I C role. So really excited to get into it. Brian Mazzaferri: I'm honored, honored to be here. Chris: And if I understand correctly, this isn't the first time you've done a podcast like this, right? Brian Mazzaferri: I don't know, like this. This is you know, special. But no, I mean but once or twice I've done pre sales podcasts. like one actually one I think we were talking about very, very early in my career. I think because I was hungry for what is this whole sales engineer thing, and I went on a a podcast. At the time they were a little more like this niche thing podcasts that people were doing. and then yes, I've also I was on in the very early days of the pre sales collective podcast, when James sort of was hurting for guests. I had known him and I think I was episode like number two or something like that. So this Chris: Amazing. Well, Brian Mazzaferri: is lucky number three. Chris: let's hope so. So l love to know a bit about how your career started, specifically how you got into pre sales, Brian. Brian Mazzaferri: sure. well I kind of accidentally stumbled. I think is maybe not an uncommon pathway, but I accidentally stumbled my way in. I had been a Salesforce, what they called an accidental admin. So I kind of worked at a company where I just we had Salesforce and I realized that it could help my function do a lot of stuff. Then I kind of became an accidental developer where I was like just on the forums and eventually trailhead became a thing and I taught myself a little bit of development. and then eventually someone was like, you you Salesforce could be a a career. And so I stumbled my way into a Salesforce implementation partner where I was for kind of like a year. And then I really wanted to work at Salesforce because I loved the tech. I was just falling in love with it. And I live in Chicago and I kept looking on the Salesforce website. And the only jobs in Chicago at Salesforce at the time were salespeople and what they called solution engineers. And I had no clue what that was, but I thought I looked at the kind of job description. It was like demoing the product and I was like, I love I just nerd out on this product all the time. I I love demos. Why not? And so I applied and got it and it wasn't until I started doing the role that I actually even really knew what it was. But I loved it. Chris: And w w w were you doing aspects of it when you were at the implementation partner and like sometimes you get pulled in for like RFPs and bids and that sort of thing? Were you were you doing Eddie pre sales or was it totally new? Brian Mazzaferri: yeah. Absolutely. I loved it. But I didn't actually know kind of what it was, right? I just thought it was like a fun thing. Yeah, I would I sold my own projects a couple times. Actually I I sold a marketing cloud project. I decided I was like I'd never used marketing cloud before, but I like was on the bench. it wasn't on a project. And so I like got my marketing cloud certification, trained myself up on it, and helped the company sell a marketing cloud project. Cause I was like, well, this this sounds fun. Why not? Chris: Okay, cool. And so so you make this transition to Salesforce and you start there as a as an S E. Like t what what what was that like and where did you go from there? Brian Mazzaferri: Yeah, it was it was a blast. Like it was the first time I felt like in my, you know, working career that I was like, this role is awesome because it was creative, you could kind of tell a story, but you it was still techie, you were very hands-on with the product all the time. It was also really fast, which I loved. Like you got to talk to all these different customers. I started in the mid market central region segment in Chicago, which was just like a really great balance to me of like speed, but also large-ish. I mean, at the time that at Salesforce that was like I don't know, a hundred to a thousand employees. So it was like Chris: Mm-hmm. Brian Mazzaferri: a a really interesting set of customers. We sometimes call it the Salesforce MBA, where you like it was not verticalized at the time. So it was just like all one day you could be talking to a you know restaurant and then a packaging company and then a tech company, and then it was really fun. It was a very kind of like high velocity. You'd do it, you'd always get a discovery, but like, you know, mostly, and then you get a discovery, and then you often like customize, you do the demo, and then hopefully that's it. Like one discovery, one demo was sort of the ideal. not that it happened every time. But it was it was a really cool way to learn business. It was an in office team, which was was great at the time. Like both the sellers and the SEs were office. So I kinda like to learn the ropes from a bunch of awesome people in Chicago. Chris: Yeah, yeah. I think particularly early in the career it's so important, isn't it, having that i in office and face to face time. Brian Mazzaferri: It's a blessing. I think it's a it's a really a challenge, you know, today. And also there's also the mix between sometimes you can be in office, but you're working with a distributed team, at which point you're like, Well, I'm in office, but I'm spending a lot of time in the conference room. you know, it Chris: Yeah, yeah. Brian Mazzaferri: was really cool. It was like actually an old school, you know, five days a week unless you were traveling to the customer or client, that it was everyone was in office. So you like saw them every day, had lunch together. Chris: Nice. So you did the the Salesforce MBA. I've never heard that one, but I like it. And you said that it wasn't verticalized at the time. Salesforce is very famous for doing the verticalization. So did that did that change? Brian Mazzaferri: It did I even in my time there, we were already kind of like on the path. So during my I suppose about three years there. And after my first year of kind of core mid market, they were starting up a new commercial manufacturing protocol, which is this idea of we're gonna take to in in the same segments like mid market and the one right above it. They were like, We're gonna take all our manufacturing customers and prospects and put them together. Who wants in? And I was like, yeah, sure, 'cause that's that sounds awesome. Like I get to be start up a new team and a new motion. And you know, my father in law had owned a a metals business. That was his like first that was his basically his whole career was you know, decades of owning a small metal finishing business. So I like had learned a bit about it from him and and it sounded fun. So yeah, I was kind of like living through the some of the early to middle stages of that transition. And then yes, by by the past few years it's been fully, fully verticalized. Chris: Okay, cool. And so you do this verticalized role for a little while and then what came what came next at Salesforce? Brian Mazzaferri: so it's pretty much that. Like I spent the my later two years in this commercial manufacturing vertical, which was a lot of fun. I mean, we built it. I was one of the first six people. It was like six people and a manager. And then even just two years later, it was like three teams, twenty-some people across it was still US, like just the the country, but it was really fun to scale. And then after that I ended up getting lured away to Slack with where I got to meet such wonderful personages as yourself. and it was there was still a lot of growth and fun at Salesforce, but it was just like after about six months of conversations, it like took me a while, but I got I got lured away to Slack and there was just too much fun and exciting stuff happening there. And I got to be the first enterprise SC in in the central region in our Chicago office, which was also supposed to be an office, but then again I started in February of twenty twenty, so that didn't last very Chris: Okay. Brian Mazzaferri: long. Chris: Yeah. And you mentioned six months so you were thinking about it for a while, but what was there a particular tipping point or was there a particular motivation that led you from the role at Salesforce, which which sounds great, to to Slack? Brian Mazzaferri: Actually, here's the funny thing. it was not I I didn't get a manager role, which was actually in hindsight the best thing for my career. Like it was one of those things I was I had gone to lead one of the or like put in my hat in the ring and interviewed to lead one of the new manufacturing teams in the vertical. And I only ended up not getting a role, which is great. I actually tell so many people, if you're thinking about leadership, just interview. Interview before you think you're ready. You're gonna learn so much from the process. but it was one of those things where I had been talking to Slack and then it was like, okay, I didn't get this role. you know, thinking it was just a moment to like kind of step back and think about what I was actually looking for in the next phase or next set of my career. I'd been at Salesforce for three-ish years. I was happy, I wasn't unhappy, but at the same time, like I the the hiring manager at the time, again, MZT, was also just like great. I kept in touch with him. We had sort of like gotten a coffee at one point, and just like slack, the allure of slack of the company and the technology eventually just the siren song, I made the leap. Chris: Amazing. So you start at Slack and what what do your roles look like there? Brian Mazzaferri: Yeah, so senior SC role. I actually took a step back. It's it's one of those things that I think I was a lead SC at Salesforce and I I went back to be a senior at Slack. I've done that Chris: Mm-hmm. Brian Mazzaferri: a couple times in my career. Actually, when I became an implementation partner, I had been a manager at my old company and then I became like a senior consultant at the implementation partner. I don't think sometimes people are afraid of that, but I've actually always relished it. I'm like, no, okay, give me a like give me a title cut or whatever. not necessarily saying you know, take go look for compensation cuts. But it's one of those things where it's like if the opportunity is there, I've always been like, I don't really particularly care about titles. and so yeah, I was a senior SC, the first enterprise specific, like the enterprise segment at Slack, in the central region. And that was like part of what was so appealing to me was helping to get to build a totally new region and segment that have been covered by the by the coasts before. and so that was a really fun time too. Obviously then within a year we were reacquired the news came that we were going to be acquired by Salesforce. So That was a whole journey too. And then I was like, okay, well, I got to be there through that transition. Obviously I felt like I had a lot of insight in how Salesforce works, having been there for a few years. And that was also when I started leading teams too, because that came with lot of growth as we went from standalone Slack to part of Salesforce. That was also even more growth that came to the org there. Chris: Yeah, yeah. So you moved into your first SE management role at Slack. What what did that feel like as a transition? Brian Mazzaferri: I mean, that's I think the hardest transition of like the SC career for folks that want to be people leaders. Like and and people underestimate it because it is such a jarring switch. Like as an SC, you're out there, you are kind of the hero a little bit. You get to, you know, be the star, you get to be like solving, delivering these awesome demos, and you get pats on the back. You don't necessarily get the giant paycheck that the AE gets, but you also don't like have a quota, so you can kind of sleep at night. I always just love that role, but then as the leader, all of a sudden you're no longer. you know, in the stage or in the spotlight out there. It's actually your team that is the most important thing. and actually that this is a line that I use for everyone that is thinking about becoming a a first line leader. It's actually from ZT. and the line is as a leader, your job is no longer to kind of solve problems. Your job is to balance tensions. And it Chris: Mm-hmm. Brian Mazzaferri: it's stuck with me a lot where it can be really frustrating for people because so many of the problems you face as a leader are just not solvable. It's not like, you have this business problem. Here's a solution. I'm going to show you how amazing it's going to be It's like, no, we've got this tension between these parties and the business that wants more out of the SC team. And you have to manage the personalities and the people and help everybody, you know, get better at what they're doing. And they're just you're just constantly trying to balance these tensions to push the business forward. and it's great. It can actually be incredibly satisfying in a different way, but it's just so it's like a almost diametrically opposed role in terms of the rewarding aspects of it compared to being in an SE. Chris: Yeah, interesting. And definitely like a completely different set of skills required. Brian Mazzaferri: Yes, yes. You I mean, so you know, it helps, right? If you've been a great SE, you have a big leg up in in terms of your credibility, right? Cause I think one of the most important things, especially as a first-line leader, is like gaining the trust of your team. Like they need to know that you're gonna be there for them, that you're gonna be able to add value to them, that your job is to make them successful. and you immediately get a ton of that if you've done their job, right? If you know how to what it takes to be a great SE in their seat, you can often help them, especially as you're recruiting and onboarding new people. You have all the answers in terms of product and how that all works. So, like you do have a big advantage there. But the actual like nuts and bolts of the job, right? Recruiting is probably the biggest one that I think people don't realize, especially if you're working at a growth or a hypergrowth company, how much of your job as a leader is constantly like bringing great people onto the team, keeping your standards high, like you know, meeting like going out there and proactively finding great people that that should join the team too, convincing them that your team is the place they want to be to develop their career. and then obviously, you know, performance management is one of those things that people don't think about a lot, but as a leader, it's a big part of your job, right? How do you continuously give really good, transparent feedback that is gonna continually make people better? and when people are struggling, it it's your problem just as much as theirs, right? Like you need to help them improve. You need to really articulate to them in a clear way what's what's going on. And so that's emotionally very difficult. There's a whole lot of stuff especially if you're working in a growth or hypergrowth company where like It's not like you're just s the the world is standing still while you do that. Like things are usually just changing around you at a at a crazy pace. Chris: Yeah, yeah. And you mentioned around you know, some of the skills being transferable and it's helpful to know the product, you know, you gain that trust with your reports. You actually, if I understood correctly, you moved as a first line manager from Slack to Rippling. So you didn't do the IC role at Rippling, you moved straight in as a manager. Wha like how what was that like? What was your experience there? Brian Mazzaferri: But that's part of why I say that. Like 'cause you don't when you come in as an external first line manager, you just don't get that. And you don't think about that until you don't have it. Where you're like, Chris: Yeah. Brian Mazzaferri: all of a sudden I'm leading this team and I can operationally help. I've like seen what good looks like in terms of running a team well, in terms of all this stuff. But like I don't know how this company works yet. So I can't really get things done for people. I don't know how this product works yet. So I can't like help them solve problems with product, which I think is like one of the core things. it was it's it's just a steeper learning curve, right? But I think there's no other way around it. You got it. I think other people might disagree, but my approach is certainly like how do you just climb that learning curve as aggressively as possible? Like how how fast could I get to the point where I could help my team solve problems with product was always like my my bar there. And it's not like I'm gonna know everything about the product. I think that's still just just unrealistic. But at the same time, I found a lot of success learning the edges, like learning the places where my team often had problems. And I would have to like quickly gain enough context to be able to help them. And then not just myself, but also Know where I had to go in the org, whether that was working with product or working with implementation in some cases or even sales, where it's like, hey, you're you're asking for this thing. This is just not possible in this way, and here's why. so definitely more of a challenge, right? You've got to you can bring some things if you're an experienced first line leader. That's part of why think it's like so helpful. Often people become a first-line leader at a company where they've been an SE. And it's really a helpful route because you can still learn so much of the other stuff with the leg up that you know the product. The first time that you go to another company as a first line leader not knowing the product, whew, it's it's gonna be an Chris: Tough cake. Brian Mazzaferri: intense little while as you get on board. Chris: Yeah. Cool. And then talk to us about your journey at Ripley, 'cause you had sort of explosive growth there. We'd love to know what yeah, your your trajectory looked like. Brian Mazzaferri: It's been a fun few years here. Yeah. I'm just about to hit my three year mark. but yeah, so I came Chris: Congrats. Brian Mazzaferri: in to lead our enterprise and channel HR S C teams here. We we were pretty small at work at the time. We only really had three teams. Zach Larek, who's a mentor of mine from Slack, I think you know as well, was Chris: Yeah. Brian Mazzaferri: was part of the reason I I came over. I really wanted to work for him again. I trust his vision. And and he was very honest with me. He's look, this is a very intense place. He was it's now I find myself in the same shoes. Anytime someone wants to work at Rippling, I'm like, hey, this is not for everybody. Like, I'm almost like, let me try and give you just a real dose of of sort of the wonderful and challenging things about working at Rippling. but he gave me an exact like great portrait and it was exactly what I wanted. So I I signed up, I joined. and then it just so happened that about six months later he got the opportunity to go lead pre-sales at OpenAI. which is, you know, also Rippling is a great growth company and OpenAI is one of those companies that is in a different kind of crazy category, right? There's not that many of those. So he is has done great things there, but also it meant that at about six months in, there was an opening around the role here, around the org here. And I had done some things, had some impact on product and some other things that they decided to give me the chance first on an interim basis, like all right, you can lead your team and run the org for a few months, see how that goes. and I did. It's one of those places where yeah, I for there was a c a two year stretch where I never had less than ten direct reports, usually Chris: wow. Brian Mazzaferri: closer to fifteen at any given time. but it was great. It's been a great journey because I went from there to then after a couple months, they officially gave me the the job leading the org. and it's just been a ton of growth since then and working with amazing people, getting to build a team has been I've learned so much along the way. You know, I've I've only been leading the org for two years now. So it's not like I've got all the answers, but I've certainly learned a bunch in the past couple years. Chris: Yeah, amazing. So that that brings us to your current role. I think a lot of people listening to the podcast, they'd probably be familiar with what a first line manager does or like th they would be able to guess a lot of it. You know, if it Brian Mazzaferri: They often work with one. Chris: yeah, exactly. but the second line management to them might be a bit more hazy. So just h help us understand at a high level what is it that a VP of solutions consulting would do? Brian Mazzaferri: Sure, sure. So the way I think about it is this like as a for first line managers, I think your core job is kind of I sometimes call it the three R's. You've got to recruit, run, and retain a high performing team. Like that is there's Chris: Mm-hmm. Brian Mazzaferri: other things, right? You have projects, you have stuff to but like at the core of it, if you can recruit great people, if you can like run the team well to deliver value, to coach those people, to grow them, and then retain them, obviously if you're the ones leaving your team, that's a challenge too. But if you can do those three things, like that is the soul, in my opinion, of the first line leader job. is like just running a great team. The second line leader job is really interesting because of course you've still got the same thing, like you're running a team of leaders, but you also start to run into responsibilities like org design. So if you're thinking about Chris: Mm-hmm. Brian Mazzaferri: the business growing, you're like, okay, how are we going to need to in the future support that? How am I going to justify staffing different SCs? Are our ratios are we going based on a ratio? How are we funding? should we be doing that in the future? Like, what is the impact of the org? How am I reporting that out to My cross stakeholders. Of course, you're also an escalation point. So anything anytime something is a challenge in the rest of your business and it's like can't be solved, it comes to you. you know, crap rolls uphill as they say. That's probably more polite than what they usually say. But but there's all kinds of things there. And I've I'm actually roughly now, now that I've got actually multiple second line leaders in my org, I'm trying to like codify this. and so I've roughly called it the three L's. So Chris: Okay. Brian Mazzaferri: it's a little a bit it's a stretch. So it's leaders. alignment and up leveling. It's a bit like reading, writing, and arithmetic, where they're now actually Rs. But Chris: I'll give you that. Brian Mazzaferri: so the thank you. Leaders, so leaders, it's like very much leaders is almost like the the three R's for but for leaders. Like you need to make a really strong leader team that's actually and it's really challenging for all the reasons that we were talking about earlier. Like you're often hiring some sometimes you're promoting internally for leaders, but often you're hiring externally too. So how are you going to find the right talent for your business, for your needs, for your roles that's actually going to make your teams really successful. and then r like, you know, obviously run, coach them, and then retain them too. So you've got kind of all of that in terms of your leader team. That's the first L. But then you've also got alignment. I kind of alluded to some of this where it's like you have to set the vision for your org so everybody actually knows where they're working. So they're all kind of like pulling in the same direction, not working at cross purposes or like duplicating efforts. and that often comes in different forms of you can do everything from you know visiting your team meeting, skip levels newsletters or videos on a regular basis. Like how are you, how is your org as a whole? Because it's not just a team anymore, it's an org. How do they know sort of like where everybody's supposed to be going and how it all fits together? and Chris: Mm-hmm. Brian Mazzaferri: then up leveling, which is funny, another real stretch for an L, but it's that's actually like it becomes a different thing even when you're at that second line level where it's not just, all right, I've got a team, I see their work. You're actually like responsible for the standards of work across your entire org now and across a group of folks that you're not going to be seeing every day. 'Cause as a second line leader, you could have, you know, some tens of people, you could have depending on, you know, Salesforce or other places where the ratios are like enforced at eight to one leaders, you could end up with fifty, sixty people in your org. And so you have to be able to kind of like up constantly think about what is this whole group of people need and how am I designing programs and projects that are actually gonna help push them forward as the business grows. Chris: Yeah, got it. And and which are some of the aspects of the role that you like and which are some of the bits that are I guess more challenging? Brian Mazzaferri: Yeah. I love I love getting in the weeds. This is funny. Like I I am still somebody who when there's a new product to help figure out, I'm still gonna jump in there and be like shoulder to shoulder with everybody, figuring out how we should demo it, petition it, how are we gonna roll out training, how we're gonna figure out this new team or this new product. I would say that's that's one of my favorite things. I've learned God, especially for the leadership. I've had so much to learn. I feel like I've I've learned so much on leaders and I'm building a great leader team. I've loved, I love the folks that are are on our team, but just like really some of the sharpest people I've ever worked with right now. there's the parts about alignment, I've had a lot of learnings to do and still Chris: Mm-hmm. Brian Mazzaferri: still learning there. I feel like it's anybody that can get 50 or 100 or 150 people moving in the same direction. I just have all the respect and I'm constantly trying to up level my game there. but then the last part about up leveling is also a a lot of fun too. I feel like there's been a ton of learnings for me there. And a bunch still to do where it's like, okay, how do we do that? I'll say up leveling is probably the least fun in s in some in some ways, because depending on how you like think about it and where you think about performance managing fitting in. Because the the reality is, especially when you start to lead and lead larger orgs, there's always gonna be people that are struggling. And so the question is like, how do you effectively let them know that they're struggling? how do you give them the opportunity to improve? And then if they can't, how do you, you know, ultimately manage them out of the business. And that's like it's just not fun. Like nobody particularly enjoys that, I think, at least not people I like to work with. sometimes we call it eating your manager broccoli internally, where it's like we know it's good. It's good for and it's good for everybody, by the way. It's not like you're trying to be mean to somebody. It's it's actually, I think, we talk about this a bunch, it's it's meaner in some ways or crueler if you're falling into that in radical candor, they call it ruinous empathy. Like you're not Chris: Mm-hmm. Brian Mazzaferri: actually telling somebody that they're not succeeding. But of course like they're gonna find out because they're not gonna get a promotion or they're not gonna like achieve things. And so like by withholding that feedback from them, you're actually not being nice. You just think you're being nice, but you're actually doing them a disservice. And so like we Chris: Yeah. Brian Mazzaferri: talk a lot about how you can give transparent and like you know good feedback to people that actually is lets them have a chance to address that, to get better, to and then often people surprise you and then can go from folks that are struggling to folks that are really sucel excelling and succeeding. Chris: Yeah, amazing. would love your thoughts on how AI is shifting things. I either your role personally or just the S E role or the sh solution consulting role at Rippling. Brian Mazzaferri: Man, all over the place. Like it's it's it's shifting it on on levels that I could not even have conceived of at the beginning of the year, if I'm being honest. Like I think I I was one of those people that was like, Yeah, I love AI, I've used it a bunch. I think for a long time I had a chat GPT subscription that I would flip on and off depending on the months. Like I like, I'm doing a bunch this month, I have stuff and then like, there's a while where I r didn't really use it. And then I went from that to somebody who has, you know, a at first a Claude Pro subscription or Cloud $200 a month and then switch to you know a Codex $200 a month subscription. And I've constantly got, you know, I a Mac Mini under my desk that is 24-7 developing software that is like some right now working on some various like demo automation software for the team. And so yes, I've very much flipped. That said, it the the ground has shifted so rapidly too, that it's like it's been a big learning experience this year. I don't feel like we've got it all on Rails and figured out. But at the same time, the other element is Rippling itself has been developing and now releasing a really solid A set of AI products that have evolved into a pretty general purpose AI toolkit. So while like a lot of the folks in the company were on Claude, there came a point a month or two ago where it was like, Hey, we're releasing skills and plugins and all this stuff. So like everybody move all your usage into Rippling AI. And that's been really cool too, because obviously for SCs who are selling this product, we're also using it ourselves and learning and growing. So actually, like we are in the midst of our own transformation. I think who knows when this will end. As long as the technology keeps changing, I think we'll keep transforming. but it's been really fun. I feel like there's I I don't know that I have specific answers. I feel like I've been on the same journey with a lot of people where I was like vibe coding and then, you know, I hit my what I've sometimes heard it described as productivity porn stage where people are you're like, automating your Slack digests and automating the crap out of every email and calendar. And then you you hit the point where you're like, all right, that was probably excessive. I didn't actually get that much value. But you learned a bunch trying it, right? and now we're in this realm where it's kind of like, okay, how are we scaling the tools for the SE org? because there's amazing things that individuals are doing. And so now I think like a lot of people are grappling with, the question becomes how are we then sharing that toolkit in a really productive way that everybody kind of gets that baseline together and all the rising tide kind of lifts all ships type of thing. Chris: Yeah, th that's definitely a recurring theme that that I've heard across episodes is there's a lot of individual experimentation going on and now it's about how do we standardize that across the team. Brian Mazzaferri: Yeah, without breaking the bank. Because that's the thing, is this as the models have gotten more expensive too for everybody that's on an enterprise plan, it's not like the tokens are unlimited anymore. Chris: Yeah, of course. Cool. So we've we've talked about your history so far and your role at Rippling. I would love to know, you know, you've had an amazing career, right? An amazing run at Rippling. What what's that down to? Is there sort of two to three habits that you would attribute your success to so far? Brian Mazzaferri: well, first of all, thank you. I'm flattered. I don't like to talk in those terms sometimes. I just I I I I feel like if for me, there's always two things that I prioritize when thinking about a role or if I'm in a role, what how I'm trying to do it, and it's learning an impact. Like where am I gonna learn the most? and then where do I feel like I could have the biggest impact? Like even going back to talking about Salesforce and leaving Salesforce, there I think You know, in hindsight, there was certainly a path that I could have had a a leadership role or a management role faster if I had stayed at Salesforce. But the allure of Slack and of like the learning, it was a you different I had spent at that point basically all of my tech career in the Salesforce ecosystem, which had been like, I don't know, seven, eight years. And I was like, okay, how I want to learn something different. I want to kind of like break outside of my safe space. and Slack was alluring in all those ways. And it was also even a an earlier stage growth company where there's just a lot more to figure out. And I and I was gonna be the first person in the central region in that segment. So I was like, you know, this felt like it just on balance felt to the like the place I was gonna have, I was gonna learn more of the things I wanted to learn and have a bigger impact. And that's kind of this is one example, but like I've kind of followed that thinking everywhere I've gone. And it's just usually like, what what can I do to learn the most, get better at what I can do. And then where am I where's my specific set of skills gonna be the most useful to to the business? And that's been I feel like if anything at Rippling, that's been the biggest thing is I've I sometimes describe it as a place where I've never worked somewhere with more important things lying around just waiting for somebody to pick up and run with them, which is great because it's it means you know there's Matt McGuinness our our chief product officer likes to say that we under deliberately understaff every project. And it's true, it's like a philosophy then because it means that everybody's job is like slightly bigger than a comparable job at another company. And I love that. But it's it's comes with its own challenges and downside. That's part of why I say like when people are considering working at Rippling, I'm like, all right, let's talk about what you're signing up for here. But for the right people who really value that sort of autonomy impact learning, like it's it's a really cool environment. Chris: Yeah. Well I I've experienced the opposite where there's too many people and not enough work to go around and that is not a motivating environment to to be operating in, right? So Brian Mazzaferri: No, I feel like it's also a recipe for politics, right? Like people start sort Chris: Yeah. Brian Mazzaferri: of making work and you no one likes to feel like they're not doing something important, so then you start doing other things that may be less important but become important and it can be weird. I b Chris: Yeah. Brian Mazzaferri: I've not my favorite environment. Chris: One piece of advice that people often get is to specialize. They might do that by industry. They might do that by the category of software that they're working with. But you've actually worked with quite different software, right? You you came, like you said, from the Salesforce ecosystem, moved over to Slack, so sort of collaboration side of things are now rippling with HR software. W would love to hear a bit more about that. Your thoughts on like specialization and and what you feel you've gained from working with actually different types of software. Brian Mazzaferri: Yeah, you know, I've done both and I feel like there's both in different realms. Like I when I think about that move we talked about at Salesforce, when I raised my hand for the commercial manufacturing vertical, that was a move to specialize and I liked it, but but again, I was chasing it because the answer was I got to like help build something new with other really smart, great people, and folks that have stayed mentors like throughout the years. I that's actually something that just to jump back to that because I think there's like a question that behind that question that I didn't say earlier where I think like Having mentors and people that you are, even if they're not like a formal mentor, but just people you look up to and like you've seen what they're doing and you think like they're doing something right. I feel like that and trying to work with those people is the key too. Like I think about part of the reason that I went this story is part of the reason I went in the commercial manufacturing vertical, is woman named Colleen Geiselhart was gonna lead that team and I really wanted to work with her and learn from her because I'd respect her work and I her career trajectory was just awesome. and she now is she's like the chief customer officer at Sprout. I think I might have butchered her title, but she leads all of like Chris: Mm-hmm. Brian Mazzaferri: pre- and post sales there at Sprout Social. and still somebody that I get coffee with regularly and and connect with. When I think about why I left Slack for Rippling, it to follow Zach because he was somebody that I'd loved working with and wanted learn from. Chris: Yeah. Brian Mazzaferri: you know, so I think there's like a a mentorship aspect and an impact aspect that I tend to put above specialization versus generalization. It's often like, What is the situation? Who are the people you're gonna work with? Are you gonna learn from them? Are you gonna be able are you the person they need on their team? And are do they think that too, by the way? Because that's like a big piece of it, right? Not even super high performing people are not always the best like working relationship with the with a different super high performing manager. It's like I I love to be in places where I can be somebody's right hand person or like, you know, some somebody's go to that like and and so it's funny because yes, in my career that's gone between specialization and manufacturing, but then Slack, I was generalist again. And actually there was a moment where at Slack, when we were acquired by Salesforce, and it was like, all right, everybody's verticalizing. I could have been put back into manufacturing because that we had a manufacturing SE team. And I I kind of said I wasn't like, no, I won't do that, but I was like, hey, I if the options out there, I would prefer not to. I'd like to try something else. And so I ended up leading Chris: Mm. Brian Mazzaferri: a team that was in our consumer business services vertical in that way. And that was fun too. We learned learned more about that. So I I feel like I I feel like specialization is great, but also I feel like specialization can lead to generalization in other ways where there's so many you can by doing different specializations, you can kind of get a really interesting frame across all the different areas of specialty. Chris: Yeah, yeah. I think there's also definitely a you don't know what you don't know aspect to it, right? I r I remember when I first joined, it's like I was supporting some crazy number, I think it was like one to twenty-five AEs. There was no other S E in the region. And so I was just getting like it was very, very transactional, but I just got so much exposure to all these different segments, all these different industries. And it was like a very nice way to quite quickly, you know, hone in on, if I were to specialise, say by industry, these are the ones that are exciting me. Brian Mazzaferri: Sure. Yeah, totally. It's it's I feel like starting general is always is always a good recommendation. Whether it's you I call it Salesforce MBA. I've heard it's referred to as the S E MBA too. Because if you are in a kind of a core or a generalist role, especially in a company or a segment where you're gonna get a lot of at bats, like you just learn so much by constantly having to learn about people's businesses. Chris: Yeah. Cool. I would love to hear a piece of advice you would have for someone in pre sales, maybe someone specifically aspiring to go into management, second line management. Yeah. What what's a piece of advice you would give? Brian Mazzaferri: it's hard to pick one. There's so many I feel like if thinking about people that want to go into management, I feel like the thing that I always say is like, first of all, apply before you're ready, right? If there is a role. You learn so much from going through process. Because then the other piece that I tell people that are in that process or or getting there is is exactly what we talked about, where it's like understand that it is a f like polar opposite role in terms of rewarding. So like really try that on for a second. Is it something where you Want to be developing people and have their success be your success, right? You're not gonna be the star anymore, you're gonna be a little more backstage. Like, really try that on mentally. And that's part of why I think that the interviewing process is so valuable, is because it forces you to kind of try that on. And often there's a presentation part of it where you're like talking about how you would approach these things. and it helps you just like try on that mindset because I think like that's the biggest thing for folks to realize. And then the other thing is just like Tay helping out. Like often managers and first line managers, even second line managers are super stretched. Like it's especially in the last few years. It's not like SE staffing has gotten thicker, you know, the ratios have gotten thinner, right? People are spread thinner. So like what can you just take off of your leader's plate? It's not gonna be everything, but like often there'll be project work or you can, you know, onboarding new people, helping them out, helping somebody that's struggling. there's all kinds of things that you can sort of do to just like get a taste of some of that work. And not not for your own glory, but just to like see, hey, if I'm, you know, helping this person out, is that rewarding to me? Is that like really get me going to have somebody else that is struggling get better? you know, those are those are the type of things I I think about. And for if it's funny, it's a little interesting from thinking about like first and second line leadership, it's often like the question is, how much do you like living in a world of ambiguity all the time? Because Chris: Mm-hmm. Brian Mazzaferri: like the the what I the what I've learned so far is like the more the larger an org you're leading and the more you continue to have to make these more senior decisions and report into you know senior leadership or e staff somewhere, your whole world is never going to be like easy black and white decisions. It's constantly gonna be operating in some level of gray and ambiguity and your whole job sort of becomes like, okay, given that, how do we move forward? How do I make some clarity for my people, my team? How do I make this build an environment that people can be effective despite the constant change and gray and ambiguity of it all? and then also accepting that probably the biggest advice piece of advice for folks that are in second line layers, like you're gonna get it wrong. You're gonna get it wrong repeatedly. Like they're just because these these decisions are are tough and there's not a right answer, like you're gonna have to make a decision, evaluate, sometimes course correct. and I think that that's also can be really hard for folks that often the best SEs are people that love getting it right. We love getting a hundred percent on the test, we love getting 110%. We want extra credit, you know, and getting getting the gold star. And it's been it's it's such a personal growth and learning experience where you're like, actually my one of my my current leader, Paul Barber, has used this metaphor with me where it's like it's like juggling glass and plastic balls, like you're juggling them all the time. and some of them are glass, some of them are plastic, and the only thing you know is that you're not gonna be able to keep them all in the air, right? Some of them are gonna drop. And so your job is to try and figure out which ones are are glass so that you're only dropping the plastic ones and you're gonna get it wrong. Like just just Chris: I like it. Brian Mazzaferri: having the emotional fortitude and the acceptance to understand that sometimes you're gonna drop a glass ball and then you're gonna have to sweep it up and figure out and move forward from there. Chris: I I'm glad that you clarified that the glass was balls 'cause in initially in my mind it was just like pieces of glass and the plastic balls and I thinking, this is I Brian Mazzaferri: no, cutting your hand out. Chris: definitely am not interested in going to second high management. Sounds nasty, but that makes a lot more sense. So Brian Mazzaferri: juggling shards of glass. No, no, no. It's it's fun. It looks good if you're doing it well, right? You got plastic and glass, you're juggling. Chris: Yeah. Brian, this has been a a a a really interesting conversation. Thank you so much for your for your time today and for your insights. A couple of takeaways from me. I love the idea of applying for the role even before you you necessarily feel you're ready and getting that that experience going through the process and actually that teaching you maybe whether or not it's a good fit. and also how things change going from first to second line management. I really like your three R's and your three L's. I know you're you're hard on yourself on the three L's, but I I I reckon I reckon they they're all good. So yeah, thank you so much. Brian Mazzaferri: Well, thanks, man. It's it's my pleasure. It's great to talk to you and catch up. it's great to be seeing you doing this. I love it's been fun to even just like see all the awesome stuff you're putting out and the folks that you're helping with this podcast. So thank you for doing it. And yeah, it's it's been a blast. Also wait, last thing I want to say on that, because you you just said it that in terms of also going to be a leader, I also know lots of people that have been a leader for a little bit and decided, you know what, I actually love being an IC. And they've made that transition back and it's awesome. Like there's no sort of like that's one of the things I love about this career is like if you if you do that for a couple of years and decide actually you want to be an individual contributor, that's a great path too. Like there's so many you know, it's it's it's more of a jungle gym than a ladder, right? You can be climbing in all sorts of different directions. Chris: Yeah, definitely. I mean, my my own personal experience, I rushed, if I'm honest, to to get into line management very early in my career just 'cause I saw that as what that, you know, that's what progression looked like. And it was only when I worked with a coach that it made me realize it wasn't necessarily lie management I was after. I was wanting to scale my impact. And there are ways to do that in IC roles. Like an AI now is is is turbocharging that, right? Brian Mazzaferri: my god. Chris: You got all this stuff around super IC. So yeah, I couldn't agree more. And you know, you can have you can have leadership without management. and yeah, I've seen Brian Mazzaferri: Totally. Chris: a lot of people make moves between the two. Brian Mazzaferri: Love that. Chris: Okay. Thanks again, Brian. All the best. Brian Mazzaferri: My pleasure. Thanks, Chris. Thanks for having me. Great to connect with you. Chris: you for listening to PreSales Pathways. If you found this episode helpful, please do follow or subscribe to the show on whichever platform you use to get your podcasts. If you can think of someone else that would find the show helpful, please share it with them. And last but not least, you can find even more resources, including a free pre-sales Pathfinder tool to explore different pre-sales career paths at chrisjamesclark.co.uk. Until next time, thank you.