AMA: Jellyfish Director of Customer Success, Roxana Fitzmaurice on Developing Your Customer Success Career

I believe that these are the must-have skills for every Customer Success Leader: Being business minded: As your scope grows, so does your responsibility to monitor performance at scale. You must have the ability to define the right success and risk signals for your business, partner closely with Operations or Analytics teams to uncover insights and then use the data to prioritize efforts and guide team execution.  People Leadership: At the end of the day, strong leaders get results through peopl ...Read More

A “typical” career path for a Customer Success Manager (CSM) often starts with building deep expertise in Customer Success and applying that knowledge through impactful customer engagements. As you grow your skills and experience, you can move up in level and scope — progressing through senior CSM roles and beyond. For those interested in leadership, there’s often a defined track that begins with a Team Lead (player/coach) or Manager role, depending on the organization’s structure and your exper ...Read More

I love asking candidates to share a time when they worked on a project or customer challenge that didn’t go as planned. People who take risks usually have a story or two about when things didn’t work out or when they faced obstacles they couldn’t overcome. In those moments, I’m looking for vulnerability, self-awareness, and the lessons learned for future projects. It can be humbling to admit to a hiring manager that you misjudged a risk or moved forward with an unrealistic timeline—but that hone ...Read More

I have to say that there is a big caveat here - you MUST be clear on your company’s strategy around rewarding talent. I’ve seen many differences in how companies approach this but also there are two things that have always held true. Frequency and percent of compensation increases (AGAIN, depending on the company’s compensation strategy) is highly dependent on the company’s financial performance. TO sustain long–term financial stability you have to be bringing in the revenue to be able to reward ...Read More

I would answer this the same way I answered the "what's your least favorite thing of being a CSM:" It’s been a number of years since I’ve been a CSM (which I still believe is one of the most difficult customer-facing roles!), but as a Leader, I think it’s wildly important to stay on top of how your CSMs are feeling about their work and their place in the organization. Two common themes I hear from CSMs regarding what frustrates them are: 1. The Internal Scavenger Hunt Chasing down internal peopl ...Read More

I don’t have a go-to framework for assessing a new opportunity but it is VERY important to get clear on what you value as a person and an employee when assessing a new company for fit. With regards to Customer Success - some of the things I inspect: Who does the CS team report up to? It can depend on the stage and size of the company but  you may find Customer Success organizations that report into a CRO or CEO, while others have a CCO. In either case, It’s important to understand how the organi ...Read More

I think Customer Success is just going to keep going down the road it's been on for years: splitting into a dual focus. On one side, we'll have the massive volume of long-tail, scaled customers. As AI rapidly improves, products and the self-serve structure around them should (and hopefully will!) get much easier to navigate. This means most customers can help themselves. BUT, the story changes entirely for large, strategic accounts. These customers run massive, complex operations, and they will ...Read More

It’s been a number of years since I’ve been a CSM (which I still believe is one of the most difficult customer-facing roles!), but as a Leader, I think it’s wildly important to stay on top of how your CSMs are feeling about their work and their place in the organization. Two common themes I hear from CSMs regarding what frustrates them are: 1. The Internal Scavenger Hunt Chasing down internal people and/or information just to address a customer's question or challenge. It's incredibly rewarding ...Read More

As a Senior CSM, you are likely regarded as a product expert—not necessarily from a technical perspective, but certainly when it comes to how your customers can successfully use and integrate your products into their workflow. Being a CSM is a fantastic way to understand the challenges they face, how they can win, and to advocate for them internally. To make the move to Management, there are several key skills you'll need to be ready to flex: The Data Miner You now have a much bigger book of bus ...Read More

I think about risk in a couple different categories. If we're talking about the beginning of the journey, I tend to lean more on monitoring stakeholder behavior for signs of trouble in the relationship. As the customer moves through implementation and launch, you can start to pull in data-driven signals that could point to potential risk.  Note: The complexity of your product will determine how soon you can start to leverage the data-driven signals! You also need to have a clear understanding of ...Read More