The Best Career in Tech is Customer Success

Having done the job for so many years, I would never pretend that Customer Success is easy.

You are customer facing, and much of what they say about working with customers is true.

You are accountable to retaining accounts, which can be impacted by a lot of factors outside of your control.

Most companies are either sales-heavy, which can cause downstream Customer Success issues, or product-heavy, which can cause downstream Customer Success issues.

People outside of SaaS and Corporate think your job is unserious — because c’mon, who’s job is “Success?”

But here’s the thing: all jobs have problems. As an Account Executive or a Product Manager, your problems are different, but there are certain inescapable pains. Depending on your skillset, these problems can be a lot easier to handle. When you’re choosing a job, you’re choosing which problems you can most live with.

The problems you face working in Customer Success are pretty manageable and actually fun to solve if you are sociable, cool under pressure, and fast on your feet.

Success in Customer Success requires someone who is good at relationship building, approaching things like a consultant, demonstrating value, and just generally being a pleasant person to chat with on a call or in a meeting.

For most people I know working in Customer Success, these skills come naturally. It’s not a lot of effort to do well. And I have a hunch that’s true for you, too.

The money is really good

The best part is that most companies value those natural abilities. A lot.

They understand they are asking a lot from their Success Teams, and that Success Teams drive a lot of value for the company, so they pay like it. It’s harder to find a Success job that pays less than $100k than it is to find one that pays more.

There’s a clear path for career growth

Most jobs become dead-ends because the only way to make more money is to become a manager or leave.

Now of course there are Lead and Management paths for CSMs, but every customer success org also has multiple splinters for CSMs as individual contributors.

The most obvious is moving upmarket — take higher value customers, increase your bonuses. But you can also move into:

• Product - best at early stage companies, where you can be the best voice of customer;

• Enablement - teach other success managers process and procedure;

• program management - get success projects off the ground;

• CS Engineer or Analysts - these new roles are popping up in large Success Orgs — essentially be the go-to product expert for other CSMs to lean on when things get really technical;

• Sales — if you have the numbers and the relationships, there’s no reason you couldn’t move into a higher-paying, quota carrying closing role.

I’m not sure there’s a better org in a tech company that positions you with so much choice! So if being a CSM isn’t your calling, your experience can help you move down new roads.

AI isn’t much of a threat

No matter how hard that one bullish VP tries, AI can’t functionally replace every org in the company, especially Customer Success.

Why do I believe this? Because CSMs drive renewals, and renewals are won with one thing the machines can’t figure out: empathy.

If you don’t believe me, ask any CSM how they saved risky accounts. Somewhere in the story, likely more than once, the CSM got on a call and listened. They listened to understand, they made the customer feel heard. That’s the secret sauce right there — the thing the machine won’t ever be able to do.

And CS is field where most leaders have actually worked as a CSM — they understand the soft skills and they fight for them.

Plus — there are a lot of AI companies hiring for Customer Success roles. If the AI could do it, wouldn’t it be doing it?

There are a lot of remote roles

I never worked at a company that didn’t have some remote CSMs. It’s one of the most common remote roles, even in non-remote companies. Enteprise, Principal, and Named Account CSM roles generally require travel, enough that it makes sense to allow the CSMs to work remotely all of the time.

But even downmarket, there are new CSM roles every single day — that’s kind of the whole premise of this newsletter! If you are looking for the perfect combo of remote + well-paying + career growth, CS is for you.

So, what is Customer Success, anyway?

In case you’re reading all this and are too shy to ask, let me explain: Customer Success is the function of managing customers after they’ve purchased. Once Sales has closed the deal, Customer Success is everything that happens next.

My experience is with Success orgs of all sizes but primary startups, so I try to provide the most down-the-middle, applies-to-as-many-companies-as-possible definition, but please know I can’t factor in every scenario.

Responsibilities

In a company with a healthy Customer Success org, generally the Customer Success Team has a few functions: onboarding, training, product adoption, upselling and cross selling, value engineering, and renewals.

There are a lot of factors that influence whether or not these actions are split into different teams and roles, or are all the responsibility of a Customer Success Manager. In my opinion, there is no right way to do this and I’ve experienced it every kind of way.

I worked as a CSM where onboarding and renewals were specialized roles, and my job was to focus on product adoption.

I worked as a CSM where my job was everything — there was no other type of Success role.

I built a CS org that at one time had onboarding as a specialized role, and then we decided to put it back under the CSM’s responsibilities.

In every case, the decision was the right one for the company and the customers. So it really does depend. Luckily, this is very often spelled out in the job description.

The ultimate responsibility of the Customer Success Org is to retain customers. Everything we do, including onboarding, training and focus on product adoption, is designed to keep a customer around and renew their contract.

Function

Companies have different ways of achieving this goal, but it generally looks something like several teams of Customer Success Managers, each led by a Manager of Customer Success, broken up by contract value.

A basic structure would be something like SMB, Mid-Market, and Enterprise. All CSMs would have roughly the same book size, but different numbers of customers. An Enterprise CSM might have a book of business worth $1m with 5 customers total, where an SMB might have $1m with 50.

Because the goal is to obtain renewals, a CSM might be juggling all sorts of tasks day to day, from conducting a business review to hosting a team training, to helping set up best practices, to reviewing metrics, to building relationships with their point of contact.

There may also be a Program or Ops team running a Scaled team — something very hot right now in the Success world. Scaled Customer Success is essentially running Success playbooks and practices at as low touch as possible. Often Scaled CSMs aren’t assigned accounts at all, but work from a shared pool of accounts. Scaled CSMs likely aren’t running QBRs or negotiating renewal contracts very heavily. Instead they’re focusing on identifying and prioritizing high risk accounts and 1:many solutions to help several accounts at a time.

How to get started

If you have project or program management experience, find PM roles specifically in a Customer Success organization.

If you have sales experience, find Account Management or Renewal roles.

If you’re at a company with a CS org, build your internal network and figure out how to get promoted into a Success role. This can come from anywhere in the company — lateral moves are a great way to get into the role without experience.

If you have non-tech experience, look for companies creating software for your industry. I wrote about this in my article, How to Break Into Tech as a Customer Success Manager.