Navigating career growth is essential for achieving goals on both the individual and managerial levels. Yet, many CS leaders lose valuable direct reports simply because they aren’t aware of how to help them develop a satisfying career path.

In August 2024, Vitally held our second “CSM Confidential” event (watch the recording here), where we and our guest experts discussed actionable ways to support healthy collaboration and pave the way forward for up-and-coming CS leaders. Here's a summary of the most important insights shared by our expert panel.

Related: "CSM Confidential" Part 1: How Work Impacts Life for CSMs — 10 Key Takeaways

Event Overview

The “CSM Confidential” virtual event series was inspired by our "Secret Lives of CSMs" report, which surveyed 679 B2B CSMs about their work experiences. During the second event, Vitally’s Director of Content Marketing Ben Goldstein summarized the report’s findings about career advancement for CSMs and introduced our expert speakers:

• Maranda Dziekonski, Vice President of Customer Success at ID.me
• Sarah Steingraber, Global Manager, Customer Success at Vitally
• Mia Kang, Scale Customer Success at Vitally

How to Help Direct Reports Navigate Career Growth — 9 Key Takeaways

1. Create leadership opportunities through project work

According to “The Secret Lives of CSMs” report, employees who have opportunities to learn and grow are 3.6x more likely to be happy at work. As a manager, even if there isn’t an immediate business need for new roles, you can still help your team members grow by assigning them leadership opportunities through project work. 

Encourage them to take on cross-functional projects where they can demonstrate their abilities, gain visibility, and build leadership skills. This approach is especially useful for team members who may be unsure about their next steps but are eager to grow and take on new responsibilities.

By strategically assigning meaningful projects, you allow your direct reports to prove their capabilities in a low-risk environment. When leadership roles eventually open up, they’ll already have a track record of success. This not only helps with retention but also positions your team members for advancement by showcasing their readiness for greater responsibilities.

2. Understand and communicate cross-functional career paths

It’s common for employees to feel limited to career growth within their own department, but as a manager, you can open up new pathways for them. 

Mia: “It's important to have a variety of career paths and options for your ICs. Not every team member wants to be or should be a people manager. This shows the team members that there is a path to make as much if not more money than a people manager."

To achieve this, make sure you have a broad understanding of career trajectories across the organization and communicate these opportunities to your direct reports. This can include roles in marketing, product, or finance, which may align with their skill sets but were previously unexplored.

You should also highlight the possibilities for financial advancement within these opportunities. Our report found that 35% of our respondents told us they felt underpaid and 44% reported that they did not receive a raise or a promotion within the previous 12 months. 

Helping your employees see beyond their current role in Customer Success encourages them to explore career possibilities they might not have considered. By understanding the broader organizational structure and knowing where employees can transition to, you support both their professional development and long-term retention in the company.

3. Help them track and showcase their contributions

It’s critical that managers ensure their team members feel valued and recognized. A significant number of our respondents said they have one eye on their next opportunity. In fact, 48%  say they're passively open to new job opportunities while 23% reported that they are actively looking for their next job.

One key way you can support your team’s career growth is by encouraging them to track their contributions regularly. 

Miranda: "I think that it's really important as a CSM to keep that running list for your biannual review of how you [and your direct reports] made an impact and really being able to speak to that in terms of metrics is really important."

Direct reports often struggle to articulate their own impact during performance reviews. As their manager, you can help by emphasizing the importance of documenting achievements and how they align with broader company goals. Encourage them to track metrics that demonstrate their value, such as customer retention rates or upsell success.

By helping them quantify their success and tell a compelling story around their contributions, you prepare your direct reports to effectively advocate for themselves during reviews or when new roles become available. This also strengthens their confidence in communicating their value to the organization.

4. Facilitate a broad understanding of the business

Sarah: “CS is like this hub in an organization. Even if you want to grow in CS, it is so important for you to understand just how businesses work. Why does sales care about what sales cares about? Or marketing, product, finance."

To help your team advance, encourage them to gain a deeper understanding of how other departments function. As Miranda shared, “"It’s important to focus outside of the CS [team] and just build your overall business knowledge. That point A to C will be so much easier to navigate."

By educating them on the business metrics that matter to teams outside Customer Success — like sales, marketing, or product — your direct reports will be better equipped to contribute strategically. For instance, knowing how Customer Success impacts net retention or revenue growth gives them a broader perspective and a greater sense of ownership over their work.

Equipping your team with this broader business knowledge not only makes them stronger candidates for leadership roles within Customer Success but also opens doors for them to transition into other areas of the company if that aligns with their interests.

5. Encourage direct reports to take charge of their career

Sarah: "One of the things I've done over the years is advocate for myself. I am not sure why folks are terrified to let their managers know that they have a desire to be promoted or move into a certain direction."

CSMs can help with this too. Encourage your team to regularly assess their career goals and create a detailed plan for achieving them. This might involve seeking out external mentors, developing new skills, or pursuing stretch assignments that build their leadership capabilities.

While your guidance is invaluable, it’s also crucial to empower your team to be proactive in managing their own career paths so that they see a clear way forward within your organization. 

As Miranda told us, "Be the CEO of your own career. Don't put the onus on your company or management to pave the path for you. You have a lot of personal responsibility in this matter."

By fostering a culture of ownership around career growth, you help your direct reports stay motivated and focused. When opportunities for advancement arise, they’ll already be prepared. Your role as a manager is to support their ambitions, give feedback, and provide opportunities, but it's essential that they feel empowered to drive their own success.

6. Support mentorship opportunities, even outside the organization

Mia: "I would almost guarantee if you reach out to somebody who is maybe a director of CS or VP of CS and that's the next path you want to go, ask them if they could talk to you about their journey. They'll probably reply yes and get on a call with you."

While internal mentorship is ideal, it’s not always feasible within every organization. Even if you don’t have the bandwidth to take on mentees you can actively encourage your direct reports to seek out mentors outside the company if necessary. 

The Customer Success community is broad and external mentors can provide invaluable insights and guidance on navigating career growth. This outside perspective can help your team members identify skills or strategies they may need to advance.

As a manager, you can support this by helping them make connections or guiding them toward mentorship programs within the industry. Encouraging networking outside of your organization also helps build relationships that could be useful for both personal growth and potential future career opportunities. 

And make sure you help with introductions! 

Related: The Secrets of a Successful CS Mentorship Program

7. Ensure fair compensation by understanding industry benchmarks

As a manager, one of your responsibilities is to advocate for fair compensation for your direct reports. Understanding industry benchmarks for various Customer Success roles is key to ensuring your team is appropriately compensated. 

Miranda: “Stay on top of industry trends...understand what is going into the making of a base salary, and then if you are getting a bonus or some kind of commission on top of that, know what goes into the making of that as well.”

Be aware of how different roles, company sizes, and responsibilities (like handling renewals or upsell quotas) impact compensation. This knowledge will help you when negotiating pay raises or advocating for promotions for your team members.

Being proactive in understanding and addressing compensation concerns not only boosts morale but also reduces the risk of turnover. Ensure your direct reports know that you are invested in their financial well-being and that you understand their market value.

8. Promote continuous skill development

Even if a promotion isn’t on the immediate horizon, as a manager, you can still encourage your direct reports to focus on skill development. Identify the areas where they can improve, whether it’s technical skills, data analysis, or communication, and provide them with opportunities to grow in those areas. This could involve additional training, new responsibilities, or cross-functional projects that broaden their skill set.

Helping your team stay focused on continuous improvement ensures they remain valuable contributors, ready for the next challenge when it presents itself. Investing in their development also reinforces that you are committed to their long-term success, which is a powerful motivator for retention.

9. Be a champion of their career aspirations

Miranda: "I know when times get tough, we sometimes, as leaders, put career development growth on a back burner. I know I'm guilty of this. You know, you're busy. You're in meetings all day. It's hard sometimes to prioritize this for yourself, but also for your team."

One of the most impactful ways you can support your team is by being a vocal advocate for their career growth. Encourage them to speak openly about their career aspirations and ensure they feel heard. 

By understanding their goals, you can offer relevant opportunities that align with their ambitions. Whether it’s stretch assignments, cross-functional projects, or salary discussions, being proactive in supporting their career trajectory keeps your team motivated and engaged.

When you champion their goals, it not only builds trust but also makes them feel more confident in pursuing their career path within the organization. Helping them align their personal goals with business needs ensures that both the company and the individual benefit.

Wrapping up

“CSM Confidential” Part 2 offered essential strategies for helping direct reports navigate their career growth within Customer Success. By creating leadership opportunities, communicating cross-functional paths, and promoting skill development, CS leaders can empower their teams to thrive.

Additionally, advocating for fair compensation and facilitating mentorship opportunities are crucial for retaining talent and fostering a culture of growth.

For more detailed insights, watch the on-demand recording of the event. Additionally, you can visit the Vitally Success Network to check out our latest resources on supporting CSMs in your organization.