How to Succeed in Your First 90 Days as a Customer Success Leader

In this episode, we’re breaking down what actually matters in your first 90 days as a CS leader and how to avoid the chaos that derails so many new leaders.

You’ll learn:
 ✔ Why diagnosing comes before fixing
 ✔ What to focus on in your 30-60-90 day plan
 ✔ How to align with stakeholders and drive early momentum
 ✔ And how to build credibility, clarity, and traction from day one

Whether you're the first CS hire or stepping in to lead an existing team, this episode gives you the structure and strategy to lead with intention.

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 0:40

If you just joined a new organization as their new CS leader, or you're about to, this episode is for you. Your first 90 days as a customer success leader will either set the foundation for clarity, strategy, and momentum, or they'll send you straight into firefighting, contact switching, and trying to fix everything all at once. And I've seen it go both ways. I've coached customer success leaders stepping into their first head of CS role. I've supported leaders inheriting teams mid reorg. I've worked with new VPs tasked with rebuilding the plane while flying it. And what I've learned is this you can't do everything in the first 90 days, but you can do the right things to set yourself and your team up for long-term success. That's exactly what we're diving into today. Whether you've just joined a startup as their first customer success hire, or you're coming in to lead a team at scale, this episode will give you the clarity and structure you need to move fast, but also strategically. We're going to break down what actually matters in your first 30, 60, and 90 days, how to avoid the biggest traps new CS leaders fall into, and the exact framework I use with clients to help them lead with intention from day one. 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. When you step into a customer success leadership role, it's easy to feel the pressure to start making changes immediately. You start spotting gaps, customer complaints, process issues, team dynamics that aren't quite working. And the instinct kicks in. You want to jump straight into fixing things. You want to prove yourself fast, but rushing in without stepping back leads to a common mistake: working on wrong problems. The first few months in any CS leadership role are about more than fixing. They're about understanding, understanding the business, the customers, the internal dynamics, the root causes, not just the symptoms. And this is why a 30, 60, 90 day plan matters. It gives you a structure for how to approach those first crucial months with purpose. When you have a clear plan, you send a very different message to your team and your leadership. You're not here to scramble. You're not here to plug random holes. You're here to learn, to assess, and to build something sustainable. The early days are when people are paying close attention, they're forming opinions quickly. If you come across as reactive or scattered, it sticks. If you lead with clarity and thoughtfulness, that sticks too. The best CS leaders don't just react to what's loudest. They take the time to zoom out and diagnose what's really happening. So when they act, their impact is meaningful. And that's what the next three months should be focused on: building credibility, building clarity, building momentum the right way. Throughout this episode, I'll walk you through a practical structure for your first 30, 60, and 90 days so you're not guessing at what matters most. We'll cover how to prioritize your time, where to focus your energy, and how to lay a foundation that sets you and your team up for long-term success. Let's get started by talking about your first 30 days. In your first 30 days, the goal isn't to change everything. You're stepping into a system that already exists, even if it's messy, even if it's incomplete. And before you can improve it, you have to understand why it operates the way it does. This is where you start thinking like a diagnostic detective. Your job in the first month is to gather context. It's about learning. And I'm not talking about just reading the onboarding deck or skimming last quarter's QBR slides. I mean real learning that is immersive, strategic, and intentional. You're here to figure out three things. Number one, how does the business view customer success? Number two, what's happening in the customer experience today? Good, bad, and messy. And number three, what are the real risks and opportunities hiding beneath the surface? And to do that, you need to go beyond surface level observation. And here's how I recommend you do it. First, start with internal discovery. Book one-on-one conversations with key leaders across the company. Sales, marketing, product, support, finance, if you can. When you meet with them, don't just ask, how do you think customer success is doing? Ask smarter questions. When you think about a customer today, what's working and what's not? Where do you see customer success having the biggest impact? What do you wish customer success should do more of or less of? Where do you think we're losing customers? What are customers telling you that maybe we're not hearing? The goal isn't to defend customer success. It's to understand how others perceive or experience customer success. You're building a 360-degree view, not just from the CS team's perspective, but from the business's perspective. Next, move into customer discovery. This part is non-negotiable. Pick a mix of customers, happy ones, struggling ones, newly onboarded ones, long-term loyal ones, and scheduled listening sessions. I'm not talking about, you know, EBRs, check-ins disguised as renewal conversations. I'm talking about real listening sessions. And ask, what's been the most valuable part of working with us? Where have we missed a mark? If you could wave a magic wand, what would you change about your experience? How do you define success with us internally? What would make it a no-brainer for you to renew, expand, or advocate for us? These are just some sample questions, right? You'll be amazed how quickly patterns will start to emerge. You're not just listening for feature requests or product bugs. You're listening for friction points, missed expectations, opportunities for deeper engagement. And here's something most people forget: shadow your team. Sit in on onboarding calls, renewal discussions, expansion conversations. Don't lead, don't critique, just observe. Watch where conversations flow and where they stall. Notice how your customer success managers position value or how they don't. And notice what questions customers are asking and how your team are responding. Because you can learn a lot from artifacts like your decks and process documents and templates, but you learn even more from live conversations where theory meets reality. And finally, don't underestimate the power of data. It doesn't have to be fancy. Even simple data like renewal rates by cohort, average time to value, or churn trends can tell you where cracks are forming. Look for patterns. Are early stage customers churning more often? Are high ARR customers expanding or staying flat? Are specific segments or industry seeing faster success or more churns? Every insight is a breadcrumb. And in your first 30 days, your job is to collect as many breadcrumbs as possible without rushing to fix the forest before you've even walked a whole path. You're building your internal map. And when you have that map, when you deeply understand the systems, the gap, the human dynamics, you'll be able to lead the real change, not just surface tweaks. That's the real work of your first 30 days. Learn deeply, listen relentlessly, and hold yourself back from fixing, just for now. Because the leaders who diagnose first, they build better, faster, and with way more lasting impact than the ones who jump straight to action. Alright, now once you have that foundation, once you've gathered all this insight, what do you actually do with it? Let's move into your 60-day focus, building alignments and priorities. Once you've done the deep discovery work in your first 30 days, you'll start seeing the big picture more clearly. You'll see where CS is thriving and where it's slipping through the cracks. You'll see which challenges are just surface noise and which ones are systemic. Now it's time to shift gears. The next 30 days aren't about launching big initiatives yet. They're about building alignment, setting the right priorities, and rallying the business around what matters most. Because here's what you need to remember customer success doesn't operate in a vacuum. You can't fix adoption, retention, or expansion inside the customer success team alone. You need sales, product, support, marketing, and the broader leadership team rowing in the same direction. And that's where alignment becomes your superpower. So step one, synthesize your discovery into a clear story. You've gathered a ton of inputs, internal conversations, customer feedback, live call observations, early data signals. Now you need to distill it. Pull together a simple narrative. Doesn't have to be like a 40-slide strategy deck. You just need to put together a clear story. Here's what's working, here's where we're falling short, here's what's putting revenue and retention at risk, here's where we have real opportunity to grow. Keep it simple, keep it human, focus on impact, not just task. And when you tell the story in a way that resonates, people start to see why customer success needs to be a priority, not just for your team, but for the business. Let's get into step two. Define your big rocks. You can't fix everything at once, and trust me, you'll be tempted to. But real impact comes from picking the right few priorities and attacking them relentlessly. Think about it like this. If we only solve three things in the next six months, which one would drive the biggest impact for customer retention, growth, or success? Maybe it's rebuilding onboarding, maybe it's tightening success planning and value realization. Maybe it's cleaning up the renewal forecasting process. Maybe it's strengthening cross-functional ownership of adoption. Whatever it is, define the two to three big rocks. And more importantly, be ready to say no to everything else that tries to creep in and dilute your focus. Step three, socialize the plan with the key stakeholders. Here's the part most news CS leaders miss. Before you launch anything, you align. That means sitting down with sales leadership, product support, maybe even your CEO, and saying, here's what I'm seeing, here's what I recommend we focus on, here's how it helps not just CS but the business. And then listen. Because sometimes you'll find that what you think is a priority isn't a top priority from a broader business lens. Or you'll uncover cross-functional dependencies that need to be built into your plan. This isn't about asking for permission, it's about building ownership. When your peers and execs feel like they've helped shape the focused areas, they're a lot more likely to support you when it's time to execute. Let's get into step four. Lock in quick wins. You're not trying to overhaul everything in your second month, but you do want to land some early credibility boosters. Quick wins that show you're not just diagnosing problems, you're creating momentum towards solving them. Maybe it's rolling out a new success planning template. Maybe it's refining onboarding messaging to tie in time to value. Maybe it's launching a weekly renewal stand-up to improve forecasting visibility. Keep it simple, visible, and tied to real outcomes. Small wins create trust, and trust gives you the runway to tackle the bigger place in your 90-day plan and beyond. So your second month is all about setting the stage. You're moving from listening mode to framing the priorities to enrolling others in the path forward. Not by dictating, not by executing solo, but by creating clarity, building buy-in, and rallying your partners across the business to care about customer success, not just as a function, but as a revenue lever. That's the real work that sets you up to win. By the time you hit day 60, you should have a few crucial things in place. Number one, a clear understanding of where the CS function stands. Number two, alignment with your key stakeholders on the biggest priorities. And number three, a few quick wins already landed to build early credibility. Now, it's time to take everything you've discovered, everything you've aligned on, and start putting it into motion. Not with giant flashy overhauls, but with targeted, high-leverage execution that moves the needle where it matters most. This phase is about turning insight into action and action into trust. Let's talk about the key steps you need to take on your third month within the company. So at this point, you'll probably see a hundred things you could fix. You'll have a backlog of ideas. Stakeholders will be surfacing new requests. Your own team might be suggesting additional initiatives. You have to stay disciplined. Go back to the two to three big rocks you identified and deliver on those first. Because what builds leadership credibility isn't ideas, it's follow-through. If you said onboarding is the number one priority, launch a pilot, tweak the journey, fix the handoffs, and measure the impact. If you said forecasting visibility was a priority, stand up the renewal review cadences, build the forecast hygiene practices, start tracking outcomes. Execution, not ambition, is what earns you more influence and more resources down the line. Next, you want to prioritize cross-functional wins. Here's something a lot of customer success leaders underestimate. Your reputation in the business is built just as much on your cross-functional impact as it is on your customer success outcomes. If you make sales life easier, they'll advocate for you. If you drive better product adoption, product will pay attention. If you tighten escalation processes, support will see you as a partner, not a bottleneck. So don't just focus on wins inside your team. Find ways to create visible wins for your cross-functional partners too. Even small things like streamlining handoffs, improving customer feedback loops, or helping sales close or renewal faster, build massive goodwill. And that goodwill will make it 10 times easier to scale your initiatives when you're ready to grow. Next, build the right operating rhythms. If your first 90 days are about diagnosing, aligning, and delivering early wins, your next chapter is going to be about building systems. That starts with locking in strong operating rhythms. Think about your internal CS team cadences, stand-ups, forecasting meetings, strategy reviews, your cross-functional cadences like renewal syncs with sales, or product feedback loops or escalation reviews, and your customer-facing cadences like success planning, executive business reviews, value realization checkpoints. Operating rhythms create momentum and accountability. They ensure you're not just reacting, you're driving proactive, predictable motion across the customer lifecycle. And more importantly, rhythms make success repeatable. When you embed the right motions early, you scale more smoothly later. Up next, you want to set up early measurement. You can't improve what you're not measuring. So you need clear leading indicators to tell you whether the moves you're making are working. Start simple. Measure time to first value for onboarding, or percentage of accounts with active success plans, or early renewal forecast accuracy, or a number of accounts engaged in QBRs. Track trends, look for patterns, and more importantly, start teaching your team to think in outcomes, not just activities. Because that shift from checking the box to driving the result is what will differentiate your customer success function long term. Next step, communicate your progress relentlessly. In your first 90 days, execution is important. But so is storytelling. You need to be the loudest, clearest champion for the progress you're making. And that means sending regular updates to leadership about wins and insights, spotlighting team success stories, sharing customer impact visibly and consistently. You're not bragging, you're building the internal narrative. The customer success isn't just the nice team that answers questions or keeps customers happy. You're the engine that protects revenue, drives growth, and strengthens customer loyalty. The sooner you start telling that story, the sooner the rest of the company will start seeing it too. So the last phase of your 30, 16, 90 day plan isn't about perfection. It's about traction. You're showing that customer success isn't just a department, it's a revenue lever. You're showing that you can set a strategic focus, execute with discipline, drive outcomes, and rally the business around the customer. And you're laying the foundation for what comes next: scaling the team, deepening the impact, and turning early momentum into sustainable growth. Okay, let's bring this all together. If you're stepping into a new CS leadership role, whether you're building from scratch or trying to scale what's already there, your first 90 days are about a few critical things. Number one, getting a clear and filtered view of the current state. Number two, aligning with your executive team on what matters most. Number three, landing a few high impact wins to build early credibility. And number four, laying down the operating rhythms that will scale with you, not just for today, but for where you want to go. You don't have to fix everything at once. You don't have to be perfect, but you do have to be intentional. When you show up with clarity, discipline, and a focus on outcomes, you're not just stepping into leadership. You're starting to change what leadership looks like in customer success. And if you want support putting this into practice, whether you're a first-time CS leader, a first hire, or someone building your team as your customer base scales, I'd love to help. I work with customer success leaders and SaaS founders through coaching and consulting, helping you build a revenue-focused customer success strategy, scale sustainably, and lead with clarity. Head to csrevspeak.com to learn more or book a free consultation call. Let's explore whether I'm the right partner for what you're building. All right, thank you so much for tuning in. Go out there, lead with focus, 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.