An Accidental Leader’s Guide to CS Leadership

An Accidental Leader’s Guide to CS Leadership

I accidentally landed in CS eight years ago via an Enterprise Sales role in a fast-growing startup.

Soon after I helped them close one of their biggest enterprise customers, I put myself in the driver's seat of setting up a CS team. Stepping into a leadership role, especially in the fast-paced world of startups and scale-ups, presents challenges and opportunities.

This transition is more than a mere change in title or salary; it's a pivotal shift in responsibility and, more importantly - perspective. You're not just an employee anymore; you become responsible for people's careers and a key player in the business's future.

In this article, I'll explore the nuances of this transition, sharing practical strategies and insights with first-time or aspiring leaders who want to navigate these waters successfully.


🔄 Transforming Into Leadership

The journey from an individual contributor to a leader involves a pivotal shift in responsibility and perspective, especially in a startup environment.

🛠️ Leadership Identity Development

Building an authentic leadership style is crucial, focusing on strategic thinking, people management, and embracing transparency.

⏳ The First 90 Days' Impact

The initial period in a leadership role is critical for setting the tone, involving strategies like 'Listening Tours' and clear communication.

🌟 Leading by Example

Demonstrating core values, empathy, and support are essential in setting a standard and fostering a culture of trust and mutual respect.

📚 Continuous Learning and Adaptation

Leadership in customer success requires ongoing adaptation and growth, emphasizing the importance of mentorship and networking.

Understanding the Transition

The transition from an individual contributor to a leader was a profound moment for me. Think about imposter syndrome punching you in the face. So many thoughts ran through my mind. Can I do this? What if I daily? How will my team respond? One of the biggest realizations that made me uncomfortable was the realization that the careers of my team, their growth, and well well-being were my responsibility.

I went from being responsible for myself to being accountable for my whole team. The next realization was exciting yet scary at the same time. The responsibility of delivering the results our enterprise customers expected of your young, growing startup. I was responsible for setting up CS and the business's bottom line from scratch.

In many ways, these realizations were both daunting and humbling. The one thing I had to wrap my head around was that I simply couldn't focus on my accomplishments alone. I had to prioritize others over me. I had to prioritize business needs and the needs of my team.

Knowing very well that often, they might not be the same. In leadership, strategic thinking and people management are inseparable twins. It's about balancing the company's objectives with the well-being and growth of your team. These were to become one of my core operating leadership principles.

Embracing the Commercial Leadership Mindset

I believe leaders are not born. They are made. They are made on the beds of several mistakes, learning, and development. Leadership is not merely about the perks and recognition. It's a serious commitment to the growth and development of your team. Stepping into this role means you are now a key player in shaping the company's future and, by extension, the lives of your team members.

You have to shift from an employee to a business owner mentality. This is one of the most critical mindset shifts one needs to make, and I see many first-time leaders make. This perspective change is vital, like it or not. You are a business unit owner.

They may not tell you, but your team is a line on the Profit and Loss (P&L) statement. And you better own up to showcasing your value repeatedly. Remember, you're not just working in the business; you're working on the business, leaving a lasting impact.

Developing a Leadership Identity

I always say, be the leader you want others to be for you. Use this as a base to create and define what your ideal leadership style would look like. Out of all other company leaders, you, as a CS leader, have one of the most delicate jobs in defining your style. You have to be amicable, you have to be able to hold your ground, and you have to be inspiring, fair, and challenging.

There are so many expectations and responsibilities on you—but above all. You have to be authentically you. Discovering and honing your authentic leadership style is fundamental. This involves a journey of self-discovery, understanding your strengths, and acknowledging areas for growth.

Authenticity means being transparent about your capabilities and continuously striving for improvement. Trust me when I say people can see through a facade.

There is no faking leadership until you make it. People respect you more if you are forthcoming about your shortcomings. In one of my first meetings as the new team lead, I was open to admitting that I did not have the answers to all the questions and challenges on my plate but that I promised to work my hardest to find the answers they expected me to know and fix the problems they had.

I was lucky early on in my career to have access to mentors in the SaaS industry due to my experience working at one of Europe's leading startup incubators. I had first-row seats and access to some fantastic entrepreneurs and learned about their mistakes and what went into making their success. This helped me accelerate and develop my leadership style.

Seeking mentorship from experienced leaders can dramatically accelerate your learning curve. One of the first things a new leader should do is seek out a mentor. Don't be afraid to seek out and ask for help.

First 90 Days: Laying the Groundwork

You never get a second chance to make a first impression. This is so true when you've been promoted from an IC to a Leader, especially if you've made that move internally.

The first 90 days of any leadership role are critical. It sets the tone for your tenure and can significantly impact your leadership effectiveness. It's also when you can make the right impression on your team. So you must prepare for your first 90 days and have a thought-through plan as a new leader.

Here is my playbook which I've refined over the last eight years and is something I coach new ladders with to get a flying start in this role.

The 'Listening Tour'

My approach in the early days was to embark on a listening tour split into two tracks. The first track involved engaging with as many customers as possible. This wasn't about making immediate changes but rather understanding their perspectives and experiences. It's about reintroducing yourself to them. Explain your new role and how this conversation will help you drive better outcomes for them.

The second track focused on structured internal dialogues with team members and colleagues from various departments. You might be thinking, but I know my colleagues already; why speak to them again? It's the same principle as with customers. You are setting a new tone of engagement. You are sharing with them your plan, reiterating what is important for you, and understanding what is important for them. This way, you can create win-win strategies.

This comprehensive listening strategy helps gain a holistic understanding of the business and customer needs. My thesis is, that most problems in CS stem from other teams. We focus on fixing upstream problems downstream in CS. These conversations help you create your roadmap of improvements. If you consistently and incrementally address these gaps identified from your interviews. You are off to the races.

Setting Expectations

One critical aspect of leadership is communication. How you communicate can define your success as a leader, especially around topics of team performance.

A common challenge for new leaders is addressing performance or behavioral issues. I get it. It is difficult to (re)establish rules of engagement with your new team. I learned it’s crucial to tackle these issues early and head-on, with clarity and promptness. Delaying or softening the feedback can lead to confusion and a lack of respect for your leadership.

One of the things I often see leaders follow is the Hamburger feedback model. I genuinely think it dilutes the essence of the message you are trying to give. But this also does not give you the license to be a jerk. Be fair, open, and timely. Give a clear example, and share clear expectations.

Consistency in your communication style and content helps establish trust. Your team should know what to expect from you and feel confident they're receiving the whole picture.

Leading by Example

An important aspect of leadership is the ability to lead by example. Your actions and behaviors set the standard for your team. Your team and others are always looking up to you. You are perpetually in the spotlight.

Here are two ways to embody this principle:

1. Demonstrating Core Values

My core values - getting things done, integrity, and transparency - guide my leadership. It's important to talk about these values and live them. For example, I ensure open and transparent communication, regularly sharing successes and mistakes with my team.

This openness fosters a culture of trust and mutual respect. (e.g., I end all our 1-1 meetings by asking for feedback from my team about my leadership style and where I can improve). And trust me, my team hasn't held back.

Why is this important? If you can act on their feedback, it sets a subconscious tone and expectation of reciprocity. Several online tests can help you determine these values. Find them, live by them, and let them guide you.

2. Empathy and Support

Empathy and Support are powerful tools in a leader's arsenal. Understanding and supporting your team members how they want to be supported is essential. One thing I love to do is understand individual motivators. Recognizing what motivates each team member is crucial.

Whether through personality assessments (use a DISC/MBTI test for this) or regular discussions, getting to know your team on a deeper level allows you to tailor your approach to each team member, ensuring they feel uniquely valued and understood.

I am also heavily invested in the growth and development of my team members and in removing obstacles that hinder their success. Because if they grow and level up, by virtue of association, you can grow and level up too.

Avoiding Common Pitfalls for New Leaders

As a new leader in customer success, navigating the pitfalls of the role is crucial. Here are some common challenges and how to overcome them:

Falling into the Trap of Not Delegating

It's a common misconception that leaders should handle all strategic tasks themselves. In reality, one of the most important roles of a leader is to develop and groom others. Delegating is not just about offloading work; it’s about giving your team opportunities to grow and learn. This not only helps in their development but also strengthens the team's overall capabilities.

The Importance of Networking and Mentorship

New leaders often overlook the power of networking and finding mentors. Building relationships with experienced professionals and investing in your own development are key to navigating the complexities of leadership. Additionally, creating allies in other teams is essential.

Remember, in the eyes of the customer, it’s not about the individual teams but the brand as a whole. A united front across departments ensures a cohesive customer experience.

Overemphasis on Data

While data is important, obsessing over it can be counterproductive. It’s about finding the right balance – using data to inform decisions without getting lost in the minutiae.

Creating a Learning Culture

Embracing mistakes as learning opportunities is vital. Our team has a tradition in our monthly meetings where we share the "Biggest Screw-Up of the Month." This practice humanizes the leadership and encourages the team to learn from their mistakes and grow. Teams must see their leaders as humans who can make and learn from mistakes. This fosters a culture where mistakes are viewed as stepping stones rather than setbacks.


Remember that leadership in customer success is a rigorous journey of continuous growth and adaptation. CS is constantly evolving, perhaps faster and more than other GTM teams.

This requires CS leaders to want to lead people that drive outcomes for the customer and the company they work for. It is equally important to acknowledge that leadership is not for everyone, and that is ok. Authenticity, empathy, and a commitment to your team's success are key ingredients to a successful tenure.

Your role as a leader is to manage, inspire, guide, and support. Remember, the best leaders leave a positive, lasting impact on their team and the organization.

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