CS Leadership Shouldn’t Require a Magic Wand

By Whitney Littlewood

You did it. You landed the promotion. You’re officially a CS leader—steering a team, driving strategy, and making an impact.

Customer Success leadership is often positioned as the next logical step for high-performing CSMs. You’ve built strong relationships, driven retention, and proven your ability to make customers successful. Leadership should be the natural evolution, right?

But here’s the catch: Your boss wants mountains moved… and you’ve got a spoon.

No budget. No tech. No data. No real authority to make the changes your customers (and your team) desperately need. Sound familiar?

If so, you’re not alone. Many new CS leaders step into roles that look great on paper but come with unrealistic expectations and minimal support.

But, you don’t just want the title, you want to actually be successful - for your career, your customers, your company and especially your brand new team! Managers actually still matter - a lot! But, are you being set up for success or are you being expected to make miracles happen in a broken, misunderstood, or underfunded function? 

Are customers jumping ship left, right, and center? Is Sales selling a dream versus a reality? Is the engineering team putting out new products on a mountain of bugs and technical debt? 

You’re going to have a hard time hitting the ground running in an environment with systemic flaws. Or, if the issues exist, do you have the buy-in, resources, and support to fix them? Driving retention and growth while building a world-class team in this type of environment is challenging, even for the most experienced of leaders. 

And that’s where things get messy.

You may find yourself burning out, frustrated, and questioning your decision and your value! But luckily, we’ve seen this so many times we’re here to help you navigate it with ease and grace.

Before you step into leadership, you need to set yourself up for success—not survival. That’s why leadership begins before you even get the job. 

These are the three areas you need to understand and make sure you are aligned with before you sign!

1. What are their expectations?

Before you accept a leadership role, dig deeper around what exactly is expected of you (by who and when). Ask the hard questions!

• What’s the most important outcome I can drive for the company?

• What are the KPIs that my performance will be judged on and what are they now?  

• Will I be managing my team’s performance and compensation decisions?

• What resources (budget, tools, headcount) are available to me?

• How does CS currently collaborate with Sales, Product, and Marketing? 

• What should the CORE ROLE of the CSM be according to the CEO/CFO/CRO?

If leadership expects transformation but isn’t willing to invest in it, that’s a red flag. The right job will come with support and clarity—not just high expectations.

2. Do you have cross-functional support? 

CS doesn’t operate in a vacuum. Your success depends on Sales, Product, Marketing, and even Finance.

Without their alignment, you’ll be stuck making promises to customers and your team that your company can’t (or won’t) fulfill. Start building relationships during the interview process. 

• Ask to meet and interview with your key counterparts from Sales, Product and Marketing. 

• Ask them what they would like to see from your team - what’s working and what’s not.

• Decide if their view of Customer Success aligns with your own - will this be a collaborative or combative relationship?

• Make them aware of the collaboration you’ll need from them.

Being a CS leader isn’t just about managing teams—it’s about navigating internal politics to ensure your function is taken seriously and has what it needs to truly drive customer satisfaction and value.

3. Do you have the right data and tools to hit the ground running?

One of the biggest shifts from CSM to CS leader is embracing the power of scale - scale isn’t about working harder—it’s about working smarter.

In order to drive solutions at scale you need access to the right data or else you’re flying blind. And if leadership isn’t willing to invest in the tools you need, be ready to walk away. Or, recognize that you’re up for a challenge and your first order of business will be getting your data in place. Set realistic time frames for this and ask up front for the support you will need. 

A tech-enabled, data-driven CS team isn’t a luxury—it’s a necessity. Without it, you’re not leading; you’re just surviving. 

Some questions to ask:

• Can I easily access the data I need, or is it buried in spreadsheets and multiple platforms?

• Do we have real-time visibility into customer health, usage, and sentiment? 

• What tasks are my team still doing manually that could be automated?

• Are our CS tools integrated with Sales, Product, and Support? 

• Are we using a Customer Success platform? 

Great CS leaders don’t just fight fires—they build systems that prevent them. But you can’t do that without support, clarity, and resources.

Before you say yes to leadership, make sure you’re set up to actually lead—not just scrape by. CS leadership shouldn’t require a magic wand or feel like an impossible balancing act—it requires the right tools, strategic backing, and a seat at the executive table.

The best leaders know this: you don’t just take what’s given—you ask for what’s needed. Step in with clear eyes, a strong voice, and the confidence to shape the role on your terms. That’s how real leadership happens and your new company will be grateful to have you!

If you’d like to go deeper please join Whitney’s LIVE interactive workshop, Unlock Your Leadership Potential, on April 9th at 11am EST / 4pm GMT. Space is limited, so sign up today!

Whitney Littlewood - Whitney is a passionate customer success leader that believes a healthy mix of data and empathy drive exceptional customer outcomes. She most recently led customer success teams at high-growth startups including UserTesting and Optimizely. Before that, she held roles in consulting, product development and marketing at companies including Adobe and Travelocity. She loves teaching and helping people grow both professionally and personally.