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Podcast Recap: Career Development in Customer Success

Updated: Jan 31

If career development has been on your mind, you’re not alone! 

Regardless of your title, individual contributor or manager, focusing on creating a path for yourself or your team is one way to get in front of the short tenure we’re seeing, especially in tech companies. 

Mark Freeman, The Senior Director of Customer Success at Pendo sat down with Strikedeck to talk about how he works with his team on career development, the skills needed in the field, and what to do if you’re not getting the support you need from your lead. 

The details

In this post, I am recapping episode 57 from Strikedeck called “Mark Freeman, Career Development in Customer Success”.

Mark started his career in talent acquisition, he led a team of recruiters and quickly found himself working at LinkedIn. His role there was essentially what a Customer Success Manager (CSM) does today. He continued to build on his knowledge as a CSM and then was given the opportunity to lead teams and run departments at a few other startups. Now he’s over at Pendo heading up their Success department. 

Strikedeck is a Customer Success Platform that helps you reduce churn, drive customer trust and loyalty, and maximize your revenue. 

Let’s dive into the three takeaways:

  1. How a leader can focus on career development 

  2. What skills should a Customer Success professional have & develop  

  3. What if there’s no career development program at your company  

How a leader can focus on career development 

If you’re thinking to yourself why it’s so important to work with Customer Success Managers and their career development, here’s the #1 reason:


There are plenty of reasons why CSMs move on from places and one of those things is purely the nature of the work. It’s stressful and creates burn out quickly. There’s the chance that a customer ghosts you on renewal or a situation escalates. All of these events slowly push a CSM to burnout and once that happens we see CSMs becoming reactive in their work, disengaged or they end up changing roles altogether. 

Talent is everything and is a good indication of what a company is capable of. For Success leaders, it’s especially important to be intentional about this since it is a new field and there’s not a lot of information around career paths. As a CSM or CSM leader, we need to be mindful of how we walk the walk, the skills that are needed, and the fulfillment needed in the customer journey. 

Leaders have to make talent a priority. There’s a lot of discussions about churn, health scores, and scaling. But what’s needed is more conversations around talent and development. Leaders need to talk more about quantifying development and how they look at operating frameworks and trends. 

Having the career development talk with your team 

Mark encourages us to have a regular interval where we have a CSM in a room and we plot out their development. This conversation can help you uncover the strides they’ve made and the gaps that need to be filled. It’s an opportunity to lead your teammate towards their development path.  

But some leaders argue that “if we start talking about career development, they’re going to want a promotion like… right away” and this is just not true. If you’re talking about career development, you can actually delay how quickly they feel like they have to be promoted. Because you’re talking about it and they feel like they’re moving down a path. Kristen, the host, adds that it’s when you’re not talking about it that people feel the real need for a tangible promotion. 

Mark calls this pacing. You are now talking about the skill mastery or S curve and if you avoid it, you leave them searching. This is an important way to build trust with your team. It’s not just your teammates having an impatient need to go title searching, it’s about developing skills and accepting challenges. The titles and opportunities will follow. 

The final thing is trickier especially for new managers, Radical Candor. Being able to break down walls, give meaningful feedback, and be willing to have tough conversations, builds trust. It’s really hard because new managers struggle with the new likability piece. But doing it in a constructive way is really key. 

What opportunities has Mark created for his team

Throughout his journey, Mark has created various opportunities to put career development into practice. 

Cross-training gives the team the opportunity to learn from each other. Empowering folks that are good at a certain thing and asking them to take the lead on training. For example: “you’re really good at QBRs, why don’t you show what you did with that customer”. 

Mentorship at different stages. There’s a mentor when someone is onboarded but we need to keep this up over time. This may mean access to senior leadership or different folks from different teams. 

Player-coach roles, Mark has talked to other leaders that aren’t sold on this idea, they think “If I create a team lead, it’s going to be too ambiguous, they don’t have all the details on what that means” that’s the point, Mark says. If you have a team lead role, you have someone that cares a little bit more about the people around them. That’s the first sign of leadership! 

What skills should a Customer Success professional have & develop  

Here are the tangible skills Mark highlighted:

  1. Have they worked at a software company?

  2. Have they managed to a metric? Can they talk about that? 

  3. Have they done a full post lifecycle before? Have they onboarded, done QBR, outcome driving, and renewal? 

  4. Have they worked cross-functionally? Have they dealt with escalations or feature requests?

  5. And how many years have they done this for? 

But Mark admits that the competencies are the harder parts:

  1. Communication (definition varies from leader to leader)  

  2. executive presences and poise – a very important trait to have

  3. Curiosity – do they do their research and dive into the data to make sense of it? 

  4. Comfortable with ambiguity – are they flexibly (especially at startups)? 

  5. Likeability – this is something that was mentioned at a Saastr talk Mark attended and he hadn’t thought about this before. Are they likable? Can people relate to them? 

Kristen also shared a few other skills she looks for: 

  1. Leadership – even if you’re a frontline CSM, you’re still leading cross-functional teams, you’re still leading your customers through the change management process. 

  2. Persuasion – this feels like a Sales skill but you also need it in Success. You’re still having to talk people into adopting your solution effectively. 

  3. Business acumen – They don’t need an MBA but they should have an understanding of business strategy. They’ll need to have good conversations with their customers and understand the WHY behind the product they’re helping to implement. And what KPIs a company is using to measure its success is really important to know. 

  4. Asking the right questions – Being able to discover properly by asking customers the right questions which get them to open up and let them come to their own conclusions.

What if there’s no career development program at your company 

Let’s break down this answer into 2 parts: for the CSM leaders and individual contributors. 

CSM leaders

Not every company is willing to invest in career development so how do we encourage a company to create a budget for this? 

Mark says it’s not an easy answer; don’t wait for a business to embrace the change or even feel entitled to it. Exemplify it! 

Go put in the sweat equity, leaders need to go make the change. Mark tells his boss and people around him how much he cares about people and talent because he does. He tries to recognize his team and give them opportunities to grow and recognize these things early. 

Then again, Mark is at a startup which feels like a bootstrap environment. He’s used to not having a fully built out team and while Pendo is now building a career development team, it’s still new but he doesn’t rely solely on it. 

For the companies that are ultra scrappy––think early-stage startups––here are some tactics:

Start off with some readings like Throw your life a Curve and Radical Candor. 

Outside of theories and frameworks, the practical advice is to ask your teams! What would they like to see more in terms of discussing their development and how often would you like to have these discussions? You’ll find that some may want to really lean into this.

And as mentioned early in this post, you have to make an interval where you talk about performance, setbacks, skills, and development. And set expectations on career growth with your team. If you think promotability is a year or two worth of results and need certain traits, you have to say it. Meet with the team and lay it out instead of saying “when the next job comes up, through your name in the hat”, it’s a different tactic altogether. 

Individual Contributor

If a leader isn’t supporting your growth, Mark recommends a blunt approach: find a new leader. But if this isn’t an option, don’t suffer in silence and have “the awkward” conversation with your lead. When you bring it up, consider the skills that you demand, layout what you want to learn, and share with your manager. 

Outside of work, get out there and go to meetups. His team is constantly attending meetups to learn more from their peers. Development doesn’t just need to happen at work. 

Lastly, your book of business is like your very own startup. Try things, learn from it, and document it as you go along. 


  1. Talent should be a hot topic at the leadership table––it’s right up there with churn and customer health scores

  2. Are you curious, good at discovery, and comfortable with ambiguity? Those are some great skills to have in CS 

  3. Team leads, you don’t need your company to back you up to start developing your team

Shout outs

Thanks to Strikedeck Radio for hosting Mark on their podcast! You can go follow them on Twitter. And if you want to hear more from Mark, follow him on LinkedIn


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