How to Upskill as a CSM: 6 Pro Tips for Surviving the Current Job Market

Jim Gonzales is the former Senior Customer Success Manager at LawVu and a member of Vitally's Success Network.


Customer Success Managers have a target on their back.

As B2B companies continue to cut costs, job security for Customer Success teams is less guaranteed than ever.

Unless your role is directly tied to a number — upsells or renewals, for example — you run the risk of being seen as redundant when company executives begin asking, "What's not bringing us revenue?"

That’s why it’s so important to understand the value you bring to your company.

With that in mind, here are my best tips for Customer Success Managers to build their skills, stand out among their peers, and advocate for themselves. Layoffs can happen without warning, so follow this advice and you’ll be a lot better prepared for the job market if you suddenly need to find a new gig.

6 Tips for Upskilling as a CSM

1. Understand Your Book of Business

The general view of CSMs is that they’re there to build relationships and provide value to the customer. But how does that tie back to the business objectives and mission of their company?

The first thing I always recommend to CSMs is that they truly understand their book of business. What’s the total value of your accounts? How are you segmenting your customers? How many big clients do you have, how many mid-market ones, how many SMBs? What were you in charge of?

Those are the types of questions that they'll be asking you in a job interview, and being able to respond with quantifiable metrics is a huge differentiator. 

By the way, “quantifiable” doesn’t have to mean “revenue impact.” Even figuring out how many projects you've worked on that contributed to the overall success of the CS team and broader company can be helpful in expressing how much value you brought to your organization. So always keep track of the major projects you spearheaded and the projects you completed.

2. Take a Deeper Interest in Your Tech Stack

When companies are looking for Customer Success Managers, they don't want to have to train them from scratch. Being able to get up to speed quickly is very important for new hires.

If you have expert knowledge of your company’s Customer Success Platform, it could make you an ideal candidate at companies that also use that platform — so build your skills while you can. 

The same goes for non-CS tools like Salesforce or HubSpot. Having experience with commonly used tech platforms will show that you won’t need much hand-holding during employee onboarding. You can even use your knowledge of CRMs and marketing automation tools to illustrate how you've been able to collaborate with other departments in your current or past roles.

3. Advise (and Challenge) Your Customers

The most important skill for a salesperson or a CSM to have is their ability to challenge the customer. That means providing customers with education or information that changes their current thinking. 

If I’m a Vitally CSM, I'm not going to spend an entire client conversation just talking about Vitally and all its capabilities and features. I want to talk to customers in a way that shows I understand the broader market of Customer Success Platforms. I want to say, “These are the trends I’m seeing out there, these are the metrics that I’m seeing." 

Then, I can draw those trends back to how they relate to my product. That way I'm not just providing information for my customer and their team to discuss, I’m also adding to the overall value that my company is bringing to the customer. 

Challenging customers and teaching them something new makes you a very viable asset to their business. You always want to be a trusted advisor that leaves your customers with more knowledge than they started with.

4. Learn How to Tell a Story

Most SaaS companies put sales on a pedestal. In every all-hands meeting, you hear about how much money the sales team is bringing in, and their stories of what it took for them to get a new customer over the finish line. 

We don’t always hear the Customer Success team share their success stories in the same way, even though we all know how important it is to retain customers. I think there's so much value for a CSM to be able to tell a story of a customer that was on the verge of churning, but because they were able to collaborate with the customer and provide value, they helped solve the customer’s pain points and the crisis was averted.

That's a story worth telling. And being able to share that to the broader company is important because it shows the value that Customer Success brings to the team. Getting in the habit of telling stories about how you've prevented churn or how you’ve helped customers grow will pay off when you’re asked to give examples of your impact in a job interview.

For more expert advice on storytelling in Customer Success, watch the debut episode of Success/ful:

5. Build Relationships Outside of the CS Department

Being a CSM is such a cross-functional role that you have plenty of opportunities to build your skills through interactions with other parts of the company. 

For example, if you dedicate some time throughout your week to seeing how your sales team does prospecting, you’ll get insights on what the customer journey looks like before a buyer signs the contract. And when a prospect does become a customer, you'll have a better understanding of the value that they were looking for initially.

Learning how marketing works at your company is equally valuable. What drew the customer to look at your brand in the first place? And of course, it’s always wise to stay close with your product managers and engineers. If you understand your solution on a deeper technical level, it'll save you from having to rely heavily on support or constantly loop in your engineering team.

Related: What Should the Relationship Between Customer Success and Product Look Like?

6. Show Up in Public

We’ve all gravitated to this remote world where we're constantly talking to each other via video, which is fine for the most part. But Customer Success is very, very personal, and having in-person interactions is very important. 

Regardless of what job I've been in, I've always made an effort to physically attend networking events or social events, and I truly believe it's elevated my career. Going to Customer Success conferences has helped me network and find opportunities, and I’ve been able to meet and hear from the CS leaders who are actually creating the trends and strategies that Customer Success professionals talk about all the time.

Plus, referrals go a long way in a job hunt, so the bigger your network the better. If you know someone at a hiring company, you get placed in a different bucket and you'll at least get one interview as opposed to getting lost among all the other candidates and possibly not hearing back from the company.

Bonus Tip: Invest in Yourself and Practice Self-Advocacy

Your company will only support you so much. Spend money to invest in yourself. Take the course/class you've been wanting to take. Buy the book you've been wanting to read. Take the trip you've been wanting to take to relax and rejuvenate. Your investment will return a hundred fold.

Practice self-advocacy by speaking up during meetings. During your 1:1s with your manager, share the impactful work you've been working on. Volunteer to speak during All-Hands or lead a discussion during Team Meetings. Speak up even if you're scared. This is how you can accelerate your growth and fast-track your career.

I encourage you to connect with me on LinkedIn as I continue to share tips and tricks on how to grow your career and upskill in this current market.

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