Your Guide to Building a Career in Customer Success

So, you want to pursue a career in Customer Success? With more companies understanding the value of a retention-first approach, the field keeps on getting hotter and hotter by the day. Based on their extensive jobs landscape data, LinkedIn even identified Customer Success Manager as the third most promising job of 2018.

With so many well-paying jobs popping up in the hottest tech enterprises and startup across the globe, it’s easy to see the appeal of pursuing a career in the field. Yet, a lot more goes into building a successful career than being at the right place at the right time. Let’s look into what it takes.

Things to consider for your career in Customer Success:

  1. Is Customer Success For You?
  2. What Does The Career Actually Look Like?
  3. How to Nail Your CSM Interview
  4. What Compensation Should You Expect?
  5. Starting Your New Position (from CS vs. or from another field)
  6. How to Become a Top Performer
  7. Paths to Leadership

Is Customer Success For You?

First, can you easily answer the question “what is Customer Success?” Before you can understand if you’re a good fit for Customer Success, you need a deep understanding of what, exactly, makes it so indispensable in today’s economy. In short, Customer Success as a business unit is responsible for managing the customer after the initial sale. This is the never-ending mission of CSMs, managing accounts from onboarding, through adoption, to renewal or upselling/cross-selling, and repeat. There’s a lot that goes into effective Customer Success Management, but the end goal is always to guide the customer to achieve maximum ROI, in turn, preventing them from churning.

Now that you know what Customer Success is, what do you need to be successful in the role? Besides being a hard worker, there are specific personality traits that indicate whether or not you will be fulfilled in this role. First, do you consider yourself an emotionally intelligent person? Being a customer advocate comes naturally if you are highly empathetic and self-aware. Second, you’ll spend a lot of time communicating internally and externally. Are you a communications master who’s comfortable translating concepts, receiving feedback, and evaluating context? Finally, do you consider yourself to be curious by nature? A CSM has to invest time and energy into learning about people, their businesses, and their priorities. You’ll need to change your game plan without getting frustrated because Customer Success is never one and done.

Take it from someone who’s gone from first-time CSM to Director of CS in less than 3 years:

“Customer Success isn’t the right industry if connecting with people isn’t what makes you happy”

– Justine Burns, Director of Customer Success at Jobber

What Does The Career Actually Look Like?

We know you’re excited, but we need to break it to you… Customer Success career development is not easy. Being a successful Customer Success professional does not happen overnight, it takes hard work, vision, and focus. Not only that, but every new career step you take gets you further into the unknown. More traditional organizations like Sales and Marketing have been structured and scaled hundreds of times. Usually, a Sales Rep progression path and their KPIs translate from one company to another, but in Customer Success, it’s harder to find common ground.

With that being said, it’s hard, but it’s not impossible – far from that. There is a lot to gain by looking to your peer’s success stories. At the speed at which the industry is evolving, it’s unlikely you’ll be able to reproduce someone else’s career progression path for yourself, but it will give you insight into what skills are transferable and where you might want to look to develop them.

So, no, we can’t tell you what a career path in Customer Success actually looks like. The good news is that you are creating your own as opposed to following the beaten trail.

How to Nail Your Customer Success Interview

Still up for the challenge? Good, now let’s look into how to actually get the job in the first place.

During a Customer Success interview, the person you are meeting with is your customer. You need to give them a snapshot of what the customer experience will be like with you at the wheel. Hence, there are a few key things you should prepare for ahead of the interview. First, do your homework. Know and understand the product well enough to demonstrate how your approach will lead to greater customer adoption. Don’t just study the product, learn everything you can about the people interviewing you and the company. This will demonstrate your ability to build rapport efficiently. If you’re thinking that you can’t possibly learn that much from the outside, welcome to the world of Customer Success. This is what you’ll have to do with your customers if you get the job. And finally, be prepared to give concrete examples of success. Bring stats from your previous positions, and be prepared to explain your numbers if needed.

This should help you sell yourself, but don’t forget to evaluate the company and the position you’re interviewing with too. The goal is to identify a mutual fit between you and your potential future employer. Be sure to understand how Customer Success, Customer Support, and Account Management relate to one another in the company. There are some questions you can ask to find out about the company culture surrounding Customer Success:

  • Who does Customer Success report to?
  • How does Success and Support work together?
  • How is the success of the team measured?

Based on the responses you get, you should be able to evaluate where the company stands in regards to customer-centricity and alignment.

What Compensation Should You Expect?

Customer Success Managers’ compensation structures vary widely across organizations. Simply put, the main difference to be aware of is base salary vs. variable compensation. Within the second bucket, you’ll find different combinations of variable compensation plans, the main components being bonuses and commissions.

Base Salary

When signing your offer letter, your base salary will state how much you will get paid. Then, whether or not you meet or exceed your goals will not affect your income. Of course, overachieving might lead to a great promotion and raise, but overall, your KPIs won’t impact your paycheck. Base salary compensation alone gets some criticism because it does not position the Customer Success team as having a direct impact on revenue.


This type of variable compensation is directly linked to revenue, as it often comes in the form of a percentage of a hard dollar value. This type of commission often means that Customer Success Managers’ KPIs are linked to renewals, upsells, and cross-sells.


This is a sum of money that is allocated to employees upon the completion of goals. Bonuses can be associated with team goals such as improving CSAT or reducing churn. While bonuses are an effective incentive, they can be perceived as a capped commission.

More employers are recognizing the ways in which Customer Success directly impacts revenue, and it’s reasonable to expect a base salary and variable compensation combo for your CSM role.

Starting Your New Position

We interviewed a number of Customer Success leaders and asked them what a brand new hire needs to know upon starting their Customer Success gig. Overwhelmingly, the response is always to get to know the product in and out. When you’re in charge of coaching customers to achieve maximum ROI from a product, you better know your most obscure features, but also the best practices that come with using them most efficiently.

Stephen O’Keefe, Director of Customer Success, advises:

“Get technical. In my experience, our best CSMs have been the ones that know the product inside and out, and the ones that also have expertise outside of the product. At the end of the day, you need to deliver value in terms of helping your customer get set up on the product and using it in a way that helps their business.”

If you’re the first Customer Success hire at your company, you also need to think long-term for the business. It’s never too early to set yourself up for success at scale, and this often means setting up the analytics systems you’ll need early on and tracking trends so that a year from now you will have something to analyze.

Now, there are some specific tips you can use depending on whether you are transitioning from another Customer Success position, from Support, or from pre-sales.

From Success

To make this transition successful, unlearn what Customer Success Management means to you. Your direct supervisor should be able to tell you, from a broad conceptual approach, what your purpose is in the grand scheme of things. There’s no single way to practice Customer Success, use your prior learnings to make informed decisions, but don’t bring your baggage to your new organization.

From Support

These two overlap in a lot of the key skills they require, but they’re actually nothing alike. To make a successful transition, learn how to think about every little thing in a proactive light. Every touch point is an opportunity to deliver value into the future. Switching to a strategic mindset takes some time and practice, but it can be learned. Eventually, you will see an opportunity in every issue that comes up.

From Marketing/Sales

You have the advantage of knowing how a value proposition is designed and communicated to trigger the initial conversion. For this transition to be successful, you’ll need to check what tends to be a strong buy-in against the necessity side with the customers and advocate for them internally. Experience in Sales or Marketing often means you’ll have an easier time communicating value to the customer, but be cautious to balance communicating with actually achieving that value.

How to Become a Top Performer

It’s easy for Customer Success professionals to feel like their time keeps on getting away from them. In order to become a top performer, focus heavily on efficiency and productivity. Enable yourself by taking ownership of your schedule and book time to log off email and perform proactive tasks. Not only should you book time into your calendar to perform proactive, high-value actions, but you also need to build learning time into your schedule. If you don’t do this, all the improvements you make to drive productivity will be temporary. To make sure each week is spent working towards improving yourself and building your career, it’s essential that you continuously learn about your industry, your product, and Customer Success. Take time to attend webinars, read articles, or attend meetups so you’re always getting better at what you do.

Once you’ve enabled yourself to succeed, you need to gain visibility into whether or not your performance is exceeding expectations. Of course, you can’t improve what you don’t measure, so, what are you measured on, and how?

Common KPIs for Customer Success Managers include – but are, of course, not limited to – Gross and Net Customer Retention (or Churn), Net Promoter Score, and Renewals.

Gross Retention measures the annual revenue lost because of churn, against the total annual recurring revenue (ARR). Net retention measures the revenue lost because of churn while factoring in upsell and expansion revenue. Net Promoter Score is a good indicator of customer sentiment, but it can be difficult to diagnose. Renewals can be measured in terms of quotas, and if that quota is your primary KPIs, consider how that should impact your variable compensation plan.

Depending on how your company measures CSM success, be sure to understand what your KPIs are, and why. Once you deeply understand the KPIs your manager has chosen to measure you on, you should focus your attention on how to impact them to push your career forward.

Paths to Leadership

If you decide that leadership is the ultimate direction in which you want to take your career in Customer Success, know that there is more that goes into it than simply being a very good CSM. There are specific management skills one should develop to become a great leader. Customer Success thought leader Kristen Hayer once told us that the first skills to master to become a great leader are:

  • Management: learn how to keep motivation high and turnover low.
  • Analytics: it only takes a few months of solid customer data to figure out where your team needs focus.
  • Finance: understand financial reports, build a budget, and interpret business models.
  • Selling: advocate for your team to other executives and the board of directors and defend your initiatives as credible, critical, and profitable.
  • Escalation: learn what it takes to make sure the buck stops with you and issues don’t move beyond you.

So, ready for this?

Building a career in Customer Success is not only rewarding but immensely exciting. We can already see how much the field has to offer, and we’re only barely scratching the surface.

Customer Success jobs at all levels of experience are popping up everywhere in the tech ecosystem, making it the perfect time to make an (educated) jump into the unknown.

Hopefully, this gives you confidence into why and how to start, propel, and achieve a successful career in Customer Success Management.