Getting Hired in a Tough Market: A Playbook for CS Leaders

In this episode, we’re breaking down how to position yourself for your next CS leadership role especially in today’s competitive market.

You’ll learn:
✔ How to clarify your unique leadership identity and value
✔ The positioning mistakes most CS leaders make (and how to fix them)
✔ What hiring managers are really looking for beyond the job description
✔ Why visibility, brand, and strategic storytelling make all the difference

Whether you’ve been job searching for months or are just starting to explore what’s next, this episode will help you show up with more clarity, confidence, and direction.

Ways I Can Help You Level Up Customer Success:

1. Value Realization Framework Online Course:  Install a repeatable system your team can run: deliver value, prove outcomes, and drive retention and expansion. Self-paced with ready-to-use templates. Learn more.
2. Newsletter: Practical, revenue-driven CS strategies in your inbox. No fluff. Subscribe here.
3. 1:1 Coaching: Hands-on guidance to roll out value realization in your org. Book a free consult call.

For more information, visit my website: Explore more resources and insights. CS RevSpeak

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. Follow Angeline on LinkedIn.

Until next time, keep driving success and speaking the language of revenue!

Transcript

Angeline Gavino 0:39

If you're a customer success leader exploring what's next in your career, this episode is for you. The market is tough right now. I've spoken to so many CS leaders that are smart, capable, experienced, who've been job hunting for months. They're not just looking for a role, they're looking for the right role, one that matches their experience, their leadership style, and the kind of impact they want to make. But in a competitive market, experience alone isn't enough. You need to know how to position yourself. What kind of CS leader are you? What strengths do you bring to the table? And how do you communicate those trends in a way that speaks directly to what hiring managers care about? Because companies aren't just hiring for a title, they're hiring to solve a specific set of problems. So if you want to stand out, you need more than a polished resume. You need a clear, compelling leadership narrative. So in this episode, we'll walk through the mindset shifts, positioning strategies, and tactical moves that will help you get noticed, get interviews, and get hired into a CS leadership role that actually fits. Let's get into it. Welcome to the CS RevSpeak podcast, where we talk about practical insights, strategies, and frameworks that will help customer success leaders who carry a revenue number, drive sustainable growth, maximize customer lifetime value, and crush their numbers. Before you update your resume, polish your LinkedIn, or start practicing interview questions, you need to get clear on something deeper: your leadership identity. Because here's the truth: titles like head of CS or VP don't really tell anyone what kind of leader you are. And when you're positioning yourself for your next role, vague statements like I'm strategic or I'm great with customers and strategy won't really cut it. You need to be able to answer three things with confidence. Number one, what kind of CS leader are you? Are you the builder who thrives in ambiguity? The operator who can scale systems and improve efficiency? The coach who level up teams? Or the strategist who partners closely with a CEO to drive revenue and retention. There's no one right answer here, but you need to know your angle because that shapes how you show up on paper, in conversations, and in interviews. Number two, what are your signature strengths? Not just your responsibilities, your strengths. What do you consistently do well that moves the needle? Maybe you've been the first CS leader higher, and you've built the entire function from scratch. You know how to navigate the ambiguity, define the charter, set up the systems, and get quick wins in an early stage environment. Or maybe your strength is scaling. You've led CS through high growth phases, matured operating models, introduced segmentation and playbooks, and built-out layered teams that deliver at scale. Or perhaps your edge lies in revenue ownership. You don't just influence outcomes, you own them. You've carried a number-led retention and expansion efforts and built CS motions that drive real commercial impact. Whatever your strengths are, you need to be able to name them clearly and speak to them with confidence. These are the things that will anchor your positioning and make your story compelling to the right hiring team. And number three, what kind of problems do you love solving? And this is a big one. Companies hire leaders to solve specific problems. If you know what types of challenges you're best at solving and actually enjoy tackling, it becomes so much easier to find roles that align with your zone of genius. It also makes your story sharper because instead of saying I want a leadership role, you can say I specialize in scaling early stage CS teams and building customer health systems that support expansion. That's memorable, that's clear, and that's what helps you stand out. So before you look outward, take the time to look inward. Define your leadership identity, because that's the foundation for everything else. So ask yourself, where do I do my best work? What kinds of problems do I solve best? What have I consistently been known for by peers, teams, or execs? Once you're clear on that, the rest becomes easier. You'll know which roles are the right fit. You'll know how to tailor your story, and you'll show up to interviews with clarity, confidence, and direction. Remember, when you don't own your narrative, people will try to write one for you, and it may not be the story you want to tell. So once you've clarified your leadership identity, the next step is elevating how you show up, not just in your resume or interviews, but in how you describe your role and your value. Because here's what most CS leaders get wrong when they're positioning themselves for that next move. They talk about what they did. They say things like, I manage a team of X number of CSMs, or I own customer retention and expansion. But hiring managers aren't just looking for someone who can manage accounts or run team meetings. They're looking for leaders who can think strategically, influence change, and move the business forward. So ask yourself, am I operating into weeds or am I setting direction? The reality is many CS leaders are stretched thin. You're leading a team, running point with customers, solving internal fire drills, and that's real work. But when it comes to positioning, you need to show how your work ties to the bigger picture. What strategic initiatives have you led? Have you reworked your engagement model to align with news segments or growth goals? Did you drive retention improvements by partnering with sales or product? Have you influenced roadmap decisions based on customer data and usage trends? Those are the stories that set you apart. So instead of saying, I worked on revamping our QBR process, say I redesigned our QBR strategy to focus on value realization and pipeline expansion. And that helped increase expansion revenue by 18%. That's the shift. That's the difference between I did this task and here's how I moved the business forward. Now, if you're still doing a lot of executional work, don't worry. This doesn't mean you need to stop. It just means you need to start zooming out and connecting the dots. Start documenting the strategic decisions you've made. Start tracking business outcomes, not just activities, and start talking about your work in terms of impact, not output. Because when you step into your next role, that's what the executive team is going to care about. Now, let's talk about something that makes a lot of CS leaders uncomfortable. Visibility. For many of us, visibility can feel like bragging. You might think, I'm doing great work. That should speak for itself. But the hard truth is, especially when you're looking for your next leadership role, people can't advocate for you if they don't know what you bring to the table. Visibility isn't about ego, it's about clarity. And it starts internally. Even if you're actively job hunting or thinking about making a move, how you show up inside your current organization still matters a lot. And I can tell you how many times I've seen CS leaders land new roles through back channel referrals. A former exec gives them a call, a peer recommends them to another founder, a cross-functional leader hears about an opening and says, you know who would be perfect for this? That's the power of internal visibility. When you lead well and build a reputation for solving complex problems, driving alignments, and being a strategic operator, your name travels even after you've moved on. How you show up at work today becomes part of your long-term brand. So ask yourself: are you seen as someone who moves the business forward? Are your stakeholders clear on the value you drive? If your name came up in a hiring conversation tomorrow, would they know how to describe what you're great at? If not, now's the time to change that. And then on the other side, there's external visibility. No, I'm not saying you need to post on LinkedIn every day or speak on stage at conferences, but I'm saying this. The more you show up, the more you're seen. That could mean sharing a few reflections on CS strategy, participating in webinars, posting a thoughtful comment on someone else's post, or just reconnecting with people in your network. Visibility builds familiarity, and familiarity builds trust. When the hiring manager sees your name and remembers your post on segmentation or your talk on customer health or value realization, they're not seeing a code candidate. They're seeing a strategic peer, someone they already trust to have a point of view. So if you're in the market for your next leadership role, don't just update your resume. Build your leadership brand inside and out. It will do more than get you notice. It will help you land the kind of role that truly aligns with what you bring to the table. Before you chase a title or jump into next VP of CS opening, pause and ask yourself, what kind of role do I actually want? Because not all CS leadership roles are created equal. Some companies want a builder, someone who can create a CS function from scratch. Others are looking for someone to scale an existing team and tight end execution. And some roles are more about firefighting and stabilization than strategy and growth. So if you don't take time to figure this out, you risk landing a job that doesn't align with your strengths or where you want to grow. One way I like to frame it is through the three Ps product, people, priorities. Let's break it down. First, product. Do you believe in what they're building? Is there a strong product market fit? Because as a CS leader, you're going to be defending, supporting, and evangelizing this product every single day. If you don't believe in it, your job will be twice as hard. Second, people. Who will you be working with? Who's on the executive team? Who will you report to? What's the relationship between CS and sales or product? The caliber and mindset of the people you'll be working with will directly impact your ability to succeed. And third, priorities. Is CS actually a strategic priority for the business? Or are they just hiring because a few customers churn and they're looking for a quick fix? Look for signs that the company values customer success, like a seat at the exact table, clearly defined success metrics, and support from cross-functional teams. You also want to ask yourself, do I want to build or scale? Do I thrive in fast-paced, high-growth environments, or more stable, mature ones? Am I energized by high-touch customer relationships or excited by automation and efficiency at scale? When you're clear on what kind of organization you want to lead and what conditions help you do your best work, it becomes a lot easier to filter through opportunities and focus your energy on the ones that actually fit. Finding the right role isn't about casting the widest net. It's about knowing what you're looking for and being ready when it shows up. Let's talk about storytelling next. Because having a strong track record isn't enough. You need to know how to talk about it. This is where a lot of CS leaders undersell themselves. They describe what they did, but not the impact. They talk about tasks, not transformation. Saying I led a team of five doesn't tell me anything. Saying I built a CS motion from scratch and improved gross retention by 15% in one year, that's leadership. That's impact. You need to frame your experience in terms of business outcomes and strategic initiatives. Ask yourself, what problems did I solve? What results did I drive? What influence did I have across teams? Hiring managers are listening for more than just what you did. They want to know how you think, how you approach complex situations, how you lead change, how you move the business forward. So don't just say we launched a new onboarding program. Say something like, I identified a drop-off in early stage engagement, redesign onboarding to close the gap, and improve day 30 adoption by 20%. That's specific, strategic, and tied to outcomes. And here's one more tip: prepare a few clear, compelling stories that highlight your leadership in action. Think about challenges you've faced, decisions you've made, and how you created results through people, process, or strategy. Because interviews aren't just Q ⁇ A questions. They're your chance to help the hiring manager see you in the role, solving real problems that matters to their business. Here's something I say often: the best time to position yourself isn't when you're actively applying. It's before that. Too many CS leaders wait until they've been laid off or they're unhappy or the company's outsizing to start thinking about their next move. And by then, you're already on the back foot. If you want to be seen as a leadership level candidate, you need to show up like one, consistently. And that means keeping your resume in LinkedIn up to date with your most recent wins. But more than that, it means showing up in the community, contributing to conversations, and staying connected to your network. Start reaching out to mentors, peers, and execs you've worked with before. Reconnect with old managers. Let people know what kinds of roles you're exploring. You'd be surprised how many opportunities come from those quiet behind-the-scenes conversations. And if you've taken a break or been searching for a while, I want you to hear this clearly. It doesn't mean you're not valuable. The market is tough right now. And I've talked to incredible CS leaders who've been looking for months is not a reflection of your ability. It's just a sign of the times, unfortunately. So instead of scrambling when the right opportunity appears, stay ready. Keep your story sharp. Keep your materials current, and keep believing in the value you bring to the table. The truth is, finding your next CS leadership role isn't just about having the right experience. It's about knowing how to position it. It's about being clear on your leadership identity, showing up as a strategic operator, not just a doer, telling the story of your impact in a way that aligns with what hiring teams actually care about, and doing all of that while navigating a tough job market that's more competitive than ever. So if this episode gave you a few aha moments or helped you see where you might be holding back, just know you don't have to figure all this out on your own. If you want support clarifying your positioning, refining your narrative, or building a strategy for landing your next CS leadership role, I'd love to help. My 101 coaching is designed for CS leaders like you. We'll work together to identify your leadership edge, articulate your impact, and show up with the clarity and confidence that gets you noticed. Check out my website at www.csrevspeak.com to learn more about my coaching programs or book a free consultation call. Let's talk through what you're building next. Okay, as always, thank you for tuning in and I'll see you in the next episode. If you enjoyed today's episode and you want to learn more about CS RevSpeak's coaching and training services, head on over to www.csrevspeak.com. I specialize in working with customer success leaders who carry your revenue number, and I look forward to helping you confidently run a revenue generating customer success team. Don't forget to connect with us on LinkedIn and join our Customer Success Leaders Hub for more discussions, resources, and networking opportunities. You can access the links on the show notes. See you next episode.