Mastering the Art of Securing Your Next Leadership Role—With the Future in Mind

Krissy: Hello and welcome to the GTM podcast. I’m your host, Krissy Manzano.

Krissy: This is where we discuss a range of topics related to hiring. Team building and leadership across GTM organizations today. And I am so excited to welcome you all. and welcome our guest, Kenny Scannell. someone I’ve worked with, been a friend with for years and known for a long time. Kenny is the VP of sales for the Americas for Klaviyo with successful stints at zoom on 24 and service source.

Krissy: He has over two decades of sales experience leading some of the most successful high growth sales teams out there. He’s been a key contributor through three IPOs and has held key senior leadership roles across several hyper growth companies, including Klaviyo, Zoom, Citrix, On24, Concentrix, now, which was formerly ServiceSource.

Krissy: He’s passionate about developing top talent, running strategy with new product launches and scaling teams as they move up market. So. Kenny, welcome. I know this is going to be an episode that I am anticipating a lot of followers and new listeners tune into, given our topic

Krissy: today. So thanks for being here. 

Kenny: Thanks for inviting me. Yeah. Happy to jump in. 

Krissy: So what we’re going to be talking about today is, mastering the art of securing your next leadership role with the future in mind. And right now, if you are in a leadership position, or you were in a leadership position, executive, whatever that might be, it feels very depressing and Glass half empty for a lot of folks going.

Krissy: I just cannot find a job. I cannot find a leadership job I rose to the top i’ve done all these things I’ve proved my worth and it’s like that’s not enough and there’s no jobs out there in the market Even with the market coming back and a lot of ways for hiring. It’s not feeling like that For leadership, right?

Krissy: And so there’s no one that I can think of that has been more strategic and successful and always moving on to their next role in a really thoughtful way. and that can be hard when there’s a lot of uncertainty and fear, right? And so. I’m excited to get into this conversation today because, if you want to talk about gold nuggets on leadership search, I know you’re going to be, one of the best to go through that.

Krissy: So, I think this is going to be a great conversation and lots of insights to come. 

Kenny: Yeah. 

Krissy: so to just, kick us off here, can you kind of share your philosophy on how you find your next leadership role, whether You’re passive and still at a company or for like a lot of people that are probably listening, they’re not at, they were, pushed out or a riff, whatever it might be, they’re not there anymore.

Krissy: Right. What’s your kind of, move on how you go to next,

Krissy: play.

Kenny: Yeah. I think there’s a few considerations. We’ve all seen an influx of messages and LinkedIn that you’ve received over the last year or two years. It doesn’t hurt to even go back to something you haven’t even responded to in the last year and a half, just to make that connection and just say, Hey, sorry, I didn’t reply back then, but I’m now in the markets and happy to talk about opportunities.

Kenny: So I think that’s a really good starting point. the other thing is, you Anytime you’re looking for a new role, it’s important that people know that you’re in the market and you’re open to looking for a new role. And then the third is the same way you’re approaching sales, you should be thinking about taking this, taking a similar approach with looking for a job, and that means that you have people working on your behalf as well as yourself.

Kenny: So you, we have great companies like blueprint and others where, let’s, let’s see what, see what they’re working on. You guys are working on stuff, other companies are working on stuff. So important you have, a search form working with you, but it doesn’t stop there. It’s the same thing again with sales.

Kenny: If you’re just waiting on inbound pipeline to come your way, you’re going to put yourself in a tough spot. I think it’s also important that you’re doing your own work too. I think building a great network is super, super important. The network that you build throughout your other companies that you work with is usually a good source for potential roles down the line.

Krissy: I love the thing you said about LinkedIn. I’ve never actually thought about that. it’s not rocket science, but it’s brilliant at the same time, because that’s probably something that a lot of folks have not thought about. Question for you on the recruiter piece. I see a lot of people use recruiters, good intent, but in the wrong way when they’re looking for their next role.

Krissy: How do you utilize a search firm in the right way? Because I think a lot of people get confused on what recruiters do, how they make their checks, right? So how do you go about that? 

Kenny: Yeah. I mean, first and foremost, I think it’s, it’s really important to understand their role and their working relationship that you’re going to have with this recruiter. So you don’t want to spread yourself across 10 different recruit recruiting firms and you’re wasting everyone’s time. And you’re talking to roles or companies that you may not be interested, just to have conversations.

Kenny: it’s important that you think about the time constraints from, from both sides, As I’ve approached in the past, I’ve selected a couple executive search firms that, usually work with very good companies. inform them on where, where my head’s at, where I’m at, where I’m at in the markets and, see if they have anything open at the time.

Kenny: It doesn’t always work out. I think there’s things that happen organically where somebody reaches out to you or the company reaches out to you directly or someone from your network. But again, it’s good to have other sources of pipeline, so to speak, again, going back to the sales analogy, you have a BDR working on your behalf, you’re working, you have CSMs sourcing pipeline. So it’s important that you’re building quality pipeline from all angles, especially in job search.

Krissy: What is your philosophy or advice for people who go, there’s nothing out there. It’s like, where do I start? So I can start with the LinkedIn, but like, if I reach out to these recruiters or these companies, I don’t have any job openings. what else do I do from there? Any thoughts of that process? 

Kenny: Yeah, there’s, that’s a tough one. I mean, there’s, you can always search LinkedIn or Indeed or some of the job forums to see which companies are hiring. and the one thing I would advise people not to do is just blindly submit your resume because especially with the good companies, they’re getting 200, 300 of these resumes and you’re just a needle in the haystack at that point.

Kenny: So if you are going to find a company that is, actively hiring on LinkedIn, Indeed, one of the job forums, make sure that you’re reaching out to the hiring manager, reach out to the, the recruiter who’s, sourcing for this role. You can usually find out, you can sometimes see the job description.

Kenny: Otherwise you could put two and two together and figure out which, which role, which title it generally would, would allow it to. and I’ve had tons of candidates do that with me. AEs have reached out to me, managers have reached out to me in the past And it’s resulted in multiple interviews, just by someone sending a thoughtful, personalized message.

Kenny: So it doesn’t just stop with a search form or waiting for LinkedIn messages to come through. Again, it’s also finding, doing your own work, personalizing your outreach and making it meaningful as you reach out to some of these companies that you know are hiring.

Krissy: Yeah, no, a hundred percent. I tell people all of the time, and I think just from our sales background, the personalization is so important and on sales execs, like, better than to just throw your story out there and talk about why you’re so great and not even understand if it aligns from that first LinkedIn message or that first email.

Krissy: So. And I don’t think a lot of people understand ATSs, which is where a lot of companies have, like Greenhouse has an ATS. It’s a really common one used in a lot of companies, right? and or lever, and if you apply for a job, it is like forever in there. So if you apply for another job, it’ll say, Hey, this person applied for this job, even if it was five years ago.

Krissy: Right. And so if you were, I’ll have people say, I just want to apply to this job because I want to work at that company. I don’t really care to stay in that position. I, I know for, for us, if I see multiple or, two or three applications for different jobs, I, unless it’s senior AE and AE, I’m like, This person doesn’t know what they want.

Krissy: They’re desperate. And I’ve got so many other people, I’m just nixing them off because I don’t have time for that. Right. Not to, to, to just like really kind of get down to, to, to business there. And so do not apply for something that you’re not genuinely interested in, but also to, if you’re not genuinely interested in that, you don’t know your, why, how in the world are you going to write an email that’s going to get their attention or a note that’s going to get their attention?

Krissy: So, I totally agree, which kind of goes to though, So the next question of how, do you, how are you selective with your leadership roles, especially in a market where many feel lucky to even land a job? How do you kind of figure that out? 

Kenny: Well, of course it depends on your circumstances. If you have the, if you have the ability to be selective and patient for the right role, then you’re going to be very thoughtful about how, number one, how, how good of a fit is it for you? and how does that map to your, to your end goals? So if your end goal is to be a CRO at some point, as an example, and you’re trying to be a, a director of sales for a company, Is the director sales experience at this specific company going to eventually lead you to a CRO role 10, 15 years down the road?

Kenny: That’s one thing to think about.I, I think I’m in terms of, in terms of situation where there’s, there’s not a lot out there and, and you’re, you’re trying to figure out, do I settle for a role? Ultimately that’s what some people are up against. The one thing I will say is you can always find a role.

Kenny: There’s always something out there. but just really do your research on the metrics, the growth rates, and the company culture. I mean, just at the highest level, you’re going to find something that’s checking enough of those boxes and, people go through situations in their career where they’re going to have to go somewhere and ride it out a little bit, and they’re going to have to spend ideally a couple years and hopefully they get, gain good experience, make the money they need to make, to get the quality of life they need and, And yeah, and then they’re, they’re onto the next one.

Kenny: But again, hopefully you’re in the, former, not the latter. And you have the ability to be selective and be very thoughtful about how that next role is going to set you up for future roles down the road.

Krissy: Right? Do you feel like it’s harder to find leadership roles today than it’s ever been in the past? Or do you feel like it’s always been hard to find leadership roles? There’s not really a difference.

Kenny: It’s a really good question. I think it’s, I want, it really depends on the type of role. So the, the higher up you get, the more difficult it’s going to be. If you’re searching for a, SVP of sales or CRO role, there’s only a handful of these open it at one time across the country or across the state or wherever you’re looking.

Kenny: If you’re looking for a frontline leader role, you’re going to get a larger, a larger swath of opportunities. So again, it really depends on your role. But you know, if I go back 10 years ago or 15 years ago, when I first got my first a sales leadership role. I think it’s a little bit easier today.

Kenny: I think back then, 15 years ago, you’re really relying on the job forums. And again, that goes back to the problem where you’re submitting something and you’re trying to avoid being a needle in a haystack. There’s definitely a lot of search firms that were popping up back then. but now I think LinkedIn is so prevalent in terms of how people are getting their roles and the connections they’re making and.

Kenny: And sometimes you’re like you’re making these LinkedIn connections where you haven’t even met this person in real life, but they could be a resource and an asset for you down the line. So the constant networking and letting people know, know you’re looking for a job. I think that’s also very important.

Kenny: I think in today’s world, it’s easier, just naturally easier to connect with people.

Krissy: Yeah, for sure. So kind of pivoting into networking a little bit. How important is networking when it comes to finding your next leadership role and how do you do it? What are the ways that you kind of go about that?

Kenny: Extremely extremely important. I’ve been fortunate enough to work for some very good companies and. What I’ve found earlier in my career, early in your career, you think that your network is this mighty powerful thing. You’ve met a CRO, you met a president, you’ve met somebody, this company, and you shook their hand once and you think you’re off to the races and that’s your network.

Kenny: And that person goes to some other company, you think you’re going to land at that company. The larger the company you work with, the bigger your network’s going to be. And I think a good example for me is zoom. Like love, love working at zoom. Very tough to leave there. When I started there, I think there was eight or 9, 000 people.

Kenny: I did pretty all encompassing global role there. So I got to know a lot of people. In some big roles there and the people these people have since gone on to other big roles at other companies and eventually down the line, these friends of mine, they’re going to other companies that could potentially be a connection for me down the road.

Kenny: So whether it’s me working with them again, or it’s me getting feedback on a potential candidate or whatever, it’s really important to get that network. The other thing I’ll say. Relate to the network is there’s multiple ways to go about it, too It goes beyond just like the people, and the people you’ve worked with and your friends their neighbors It it’s also interacting on linkedin.

Kenny: It’s also getting in the sales communities the the pavilions, bravados, etc of the world a lot of great connections in there there’s job forums and in some of those channels as well, so you know in this In this 2024 world where everyone’s online, it’s a digital world. You’re meeting people digitally, that you haven’t actually met in person.

Kenny: Sometimes leverage that whole world that goes beyond just the people you’ve worked with. So again, when you’re looking at, looking at potentially getting a new role, you have to use every angle and going beyond your, your network and the people, the people in your digital network also think about connections that you can be making.

Kenny: And if you’re thinking about a leadership role, let’s say you’re going to, you want to go to a series B, series C company, you want to be a VP of sales. Look at, look at all the VCs and PEs that are, that are hiring, that are connected to these portcos that are hiring. A really good opportunity to connect with people from the VCs or the PE firms.

Kenny: again, in any time you, anytime you go through interviews, make sure you connect with people on LinkedIn. Like I’ve interviewed, I’ve, there’s been times where I haven’t, haven’t gotten jobs before, but I’ve connected with the, the board member that came from VC XYZ and, and I’ve kept in contact with these people.

Kenny: And again, down the line, there could be a better fit for one of their other portfolio companies that could eventually get you in the door. So again, exhausting all angles. Very, very important.

Krissy: Yep. For sure. What about if you have been a leader at really small startups? So, they’re under 100 people, sometimes under, well, you really probably aren’t a CRO or in a certain outside of founder at a company that’s 50 and under, but 100 and under, how do you utilize your network? That might be smaller from that standpoint? 

Kenny: Yeah. Again, I think it goes back to your LinkedIn network, the sales communities that you can join. what I will say is like when you, when you start to, when you go from smaller company to smaller company, naturally your network’s going to be less to your point. so you should always think about that as you’re, as you’re going for your next roles and at some point it is very valuable to get the big company experience under your belt.

Kenny: It’s important to kind of check all those boxes. And I, again, I just think about checking all the boxes, throughout, throughout my career. Eventually you get to the point where. Hopefully you want to be a CRO and you’ve experienced this, you’ve done that, you’ve accomplished this and you’ve checked all those boxes.

Kenny: so again, if I think for the small company, small company, small company, VPs, directors, there’s always other PEs and VCs that are hiring for these roles. And, and a lot of times they’re looking for people that have scaled a company from 10 million to 30 million and 10 million to 50 million. They’re not always looking for somebody that scale the company from 500 to a billion.

Kenny: Sometimes that early experience is more valuable than somebody that’s, that’s been more tenured. So it kind of works both ways, but you can also find yourself working for small company, small company. Sometimes it’s tough to break into the big company when you’re coming from the smaller companies.

Krissy: having. Having a diverse background that allows you to be the right candidate for more roles is huge, right? Versus kind of pigeonholing yourself into only one type of role. which kind of leads me to a question of like, let’s say you’re a CRO or a CMO, whatever it might be. do you think that in your job search, you should look specifically for That title role, or do you think it’s strategic potentially to take something, maybe VP level.

Krissy: I’ll be even director level. Like, what are your thoughts on how to be strategic and when to kind of know when what’s the right play there? 

Kenny: Yeah, I love this question. I think people, people naturally have the tendency to look for that big title. they want to get to their end goal as quickly as possible. There’s a level of patience that we need as we’re going through a search. And sometimes it makes more sense to get a number two role with a larger company.

Kenny: Before you step into that big, big role. I can’t even say that myself. I spent eight years or so at on 24 and had a great run, took them through an IPO. got a VP of sales role there probably halfway through. So that kind of brought me to the point where I could eventually get in the door at Zoom.

Kenny: Zoom helped me get in the door at Klaviyo. It’s not the number one role, it’s a number two role. But Klaviyo is a, you can look at the, the public filings. It’s a, it’s a large company, in terms of revenue. And I believe that eventually whenever I go for a larger role, that experience will help me get there.

Kenny: You enter these crossroads in your career. And the one thing, one example, I’ll give you Krissy, earlier in my career, back at on 24, I had the opportunity to be a SVP of sales for a series B, series B, series C company. They’re probably 15 million ARR, growing decent. so I could have had that top, top seat if I wanted back then, but I decided to wait it out, got more experience, got through the IPO.

Kenny: I went to Zoom, got more great experience, went to Klaviyo. So again, I look back at that decision, that fork in the road. And I think if I took that, we probably would have been successful, but you know, I also probably would have found myself going to another small company and nothing wrong with that at all.

Kenny: But for me personally, I want to work for a little bit more mature and larger companies, and eventually get to that tough spot.

Krissy: Yeah, no, it’s really hard to untether yourself from the expectations that others have. Of you whether you are a people pleaser or you are confident as can be when you start moving up or you’re hitting the top if you do anything that deviates from that people will Absolutely judge you or look at you sideways and it’s Even if there’s nothing bad going on, right?

Krissy: Why would they not take that? Or like, why would they go and take this? There must be something wrong. And it can, I think a lot of people struggle with that more than they will admit. And, and to be able to untether yourself from that and say, I’m going to be strategic here because it has a short term, but also a long term play for me is just key.

Krissy: And I think that example is, is absolutely perfect. Not just for folks moving up the leadership. path right now of how to be strategic, but also the ones that have hit the quote unquote top, right? And removing, themselves from having to stay there versus how can I go somewhere where I can just crush it and like, and still be a leader and get a background that’s different than, this company and this size has given me.

Krissy: So. I think that’s fantastic advice, and it opens up a lot more job opportunities when you, when you untether yourself from that. So, kind of reflecting on your journey, what advice would you give, not that you haven’t given great advice already, to emerging leaders who are trying to strategically plan their career trajectory? And maybe you’ve already answered this, but, 

Kenny: Yeah. I’ll, I probably answered some of it, but to elaborate further, think about how’s your next role going to set you up for the role after that? And I think that’s something that people don’t really think about. And what I mean by that is if you want to, if you want to be a CRO at a, let’s say a 500 million company is, is the decision of me going to a 30 million AR company as a SVP of sales.

Kenny: Is that the, is that the role that’s going to get me to the 500 million company? Possibly. I mean, if, if, if I went from 30 million to 400 million and grew the company and had a great story, then yeah, I could probably do that, but that’s going to take a lot of time. so if I go to another company, that’s a more established company, put a, put a big numbers, have a lot of success, Come back with a great story.

Kenny: that’s ultimately what’s going to get you to the next level. it’s the experience, it’s the story, it’s a network. Those are the three things that really stand out.

Krissy: yes. I mean, if you just heard that, you should. Rewind the last 15 seconds and hear it about 10 more times, just so it sticks in your head, because it might be one of the best pieces of advice on this episode. if not the best piece, you got to think, you got to think ahead, because when you start doing that fear stops driving, being in the driver’s seat, which is hard.

Kenny: I’ve just seen this so often where people are very short sighted in the decisions that they’re making on their career. Again, they go after that big title, they go after a big OTE and make that short sighted decision and they kind of gloss past. A lot of the key elements and things that they’re looking to experience in their journey before they get to that top seat, if that’s a, if that’s what they want to do.

Kenny: So again, it’s really easy to do. But again, keep that longterm vision in mind. And is this really going to catapult you by making this decision? Possibly you may make a little bit more money going to this company. But you can also sacrifice a little bit more money and do better down the road. If you go to a larger company, as an example, So again, every situation is different, but definitely keep the long term in mind.

Krissy: A hundred percent. It looking back, is there anything you would have done differently in your career? Just given the job markets ups and downs today, 

Kenny: Not necessarily. Well, actually one thing. So, when I was leavingServiceSource, so you and I worked together at ServiceSource some years back. it 

Krissy: don’t say how many, 

Kenny: exactly. It was time for me to spread my wings and do something different. And, when I did, I was kind of going back and forth between a couple of companies and.

Kenny: I’ll just mention the company. It’s fine. So I went to Citrix, Citrix, great, great company. 

Krissy: The juicy scoop. 

Kenny: Great reputation. but Citrix just acquired a company, called Podio. So I had the opportunity to come on and be their first head of sales. so again, on the surface, really good opportunity. In the beginning days it was.

Kenny: But for what I’ve seen historically, and I think other people can vouch for this and not a knock on Citrix, but sometimes they, they don’t always know what to do with their acquisitions. And not every acquisition fits either. They made some great ones and then, you’re not going to, you’re not going to bat a thousand percent on every acquisition.

Kenny: So I think that was one of the ones where I think they had a tough time figuring out where things fit. So I Citrix because, big name company, opportunity to be the head of sales and you walk into a situation that’s more chaotic, chaotic than you realize. And eventually you’re not progressing that way you need to in your career too, and it can actually slow you down.

Kenny: So that’s one thing I’ll look back on is my Citric experience. Again, I met some good people there and everything. But yeah, yeah, I think you have your learnings along the way.

Krissy: I totally forgot about that. And also if you’re on this podcast, we’re going to make sure we get the scoop. So thanks for sharing. It’s one of those things where. It’s, it’s a great example of where, you can look at stuff and it can, it can, so things that can make you feel good aren’t always necessarily good or strategic for you.

Krissy: Right? And so we’ve got to get past the feeling and really unpeel those layers a little bit more like, is this really, I remove all the expectations. If I remove the fear and the what ifs, and I just say, if I didn’t have any of these things here, what would I choose? It actually makes it a little bit more simple and it kind of leads us down, I think, a more natural path. So 

Kenny: Yep. 

Krissy: before we wrap up, I know we’re getting to the end of time here. We could do this for, for hours, I feel like, but could you share one leadership lesson that has been particularly impactful for you which our listeners could apply to their own career?

Kenny: I would say, a couple of things. Number one, within a company, build your network, talk to people, build relationships, get to know people, these relationships will last a lifetime. And, assuming you have a long career, you’re going to run into these people at some point down the road, either they can help you.

Kenny: You can help them, that these relationships are long lasting. I think something that’s more tactical, which is probably fairly obvious is, As you move further up the leadership stack, guard your calendar. It doesn’t mean that you don’t take meetings, but oftentimes I found myself, or I find myself with my whole day just completely booked.

Kenny: I’m catching up on slacks and emails after hours. Kills your quality of life. You’re stressed. So the trickle down effect is real. So what I’d recommend is definitely take a couple of, hour and a half, hour, whatever it is each day, and also think about getting outside, going for walks. And it’s so easy to, in this new world, to just take every meeting on zoom.

Kenny: If you work remote and you’re just going zoom to zoom all day, go back old school, if you’re gonna have a one on one with one of your leaders or a rep, and you don’t need to share your screen, think about walking around the neighborhood and getting that, the mental sanity back in place and walking and talking. So very small things there, but hopefully helpful for somebody listening.

Krissy: Yeah, no, I think that’s great. So Kenny, thank you so much for being on the Talent GTM podcast today. I’m sure your advice has not only helped plenty of listeners, but probably has them thinking about more questions that they want to ask, and go through. So tell them where they can find you, best way to reach out if, if they do have questions. 

Kenny: Yeah. Always happy to help. you can find me on LinkedIn, Kenny Scannell. I think my, link is actually linkedin.com slash Kenny Scannell. So it should be easy to find there. Again, please reach out with any questions. Happy to help and happy to mentor people along the way.

Krissy: Awesome. Well, thanks for joining us on the talent GTM podcast. Don’t forget to subscribe to our series on Spotify, Apple podcasts, or at blueprint expansion.com. See you in the next episode. Bye guys.