So here you are, building the next up-and-coming SaaS tool with the ever-so-common recurring revenue model. Things are going well. Your customers seem to love you, and why wouldn’t they? Your product is incredible! You and your growing customer base seem to be linked arm in arm, skipping into the sunset.

More and more users sign up. Your Product Team is innovating and designing the next up-and-coming releases. Your Support Team is answering tickets and solving problems at warp speed. The Sales team is killing it and closing deals. All seems well.

Then it happens.

The first break up.

It hurts.

You do not understand what happened. You thought that everything was okay. They paid you last month. And now, and now, this!

You ask yourself, how can I get ahead of this? How could I have known? How could I have been more proactive and maybe saved this relationship? And then it occurs to you. You need Customer Success!

But where to start? How do you hire the right first CSM to help with building that important proactive model?

It can be challenging to hire for a role in a department that doesn’t yet exist at your company. As someone who has built out Customer Success from the ground up many times now, this is a model that has proven successful for me and various others that I have mentored.

Step 1: Determine the Price of Admission 

Resume review and phone screen

When you first post the job, you will receive a lot of resumes. A lot of resumes. Sifting through resumes is hard, but you have to filter out applicants that don’t meet your basic requirements (like online dating!). “Must like sushi, long walks on the beach, and Netflix binging.”

But seriously, filtering out candidates will be crucial in finding your perfect candidate. Beyond my commonly used filters, looking for continuous growth, outcomes achieved, success on key metrics and type of CSM they have been (B2B, B2C, high-touch, and so on), here are a few other things I look for as my price of admission.

  • The first person in any role in your department should ideally have experience in that role. I aim for a minimum of 2-4 years with proven success. This level of experience ensures that the candidate has been in the trenches of customer success and understands what works well and what doesn’t.
  • While someone who has had success at their role is great, I also look for folks who talk about failures or what didn’t work and what they learned. It’s okay to not always succeed as long as you learn from that and can clearly articulate the why’s and how those scenarios will be avoided going forward.
  • Require a writing sample before you bring anyone in for face-to-face. The majority of your Customer Success Team’s day-to-day is written communication. This is key. I generally request:

A brief introduction of themselves to their new customer and how they will add value during their relationship, and a short synopsis of a couple of advanced features (on your product) that may help their new customers’ workflow and provide an improved ROI.

Step 2: 1st round face-to-face! They’ve arrived. Now what?

Once they’ve passed the “Price of Admission,” let’s see how they are in action! Sticking with the dating theme, once they’ve checked off all of your initial filters, they have now moved into first date territory. We will call this the “coffee date.” There will be certain things that you will screen for in your first coffee date to determine if you will make a longer commitment, like a dinner date. The same theory applies to your first Customer Success Managers interview. Here are some very specific things I do that have proven to be successful.

  • Construct a well-balanced interview team that will provide different perspectives. I generally like to pull in someone from Sales, Support, and, if possible, Product. These will be key internal partners that the Customer Success Manager has to work closely with.
  • We conduct four exercises with all CSM candidates to get a true understanding of how they think. You (the hiring manager) are looking for proactive thinkers. This is a huge differentiator that will help with the success of your overall customer base.

Exercise 1 

On the whiteboard, please map out your current customer lifecycle (at your current employer or previous) and the various phases of a customer’s journey through your product. How have you guided them through these phases successfully?

Hiring Manager: You are looking for their understanding of the customer lifecycle and the phases a customer goes through and specific examples of how they’ve ushered this growth. (Onboard, first value, growth, renewal, start the cycle again)

Exercise 2 

Now that you’ve done some research on our product, who we are, and how customers use our product, what are some key data points that you would use to define customer health?

Hiring Manager: You are looking for their understanding of your product and how they view health. The typical answer would be log-in data, usage data, MRR/ARR, previous upsell/expansion data. Look for answers that are specific to your product. 

Exercise 3 

This is your customer base. All things regarding these customers are equal. They have similar ARR and are from the same industry/market segmentation. They solve the same issues in the same region; the key is everything is pretty much the same. 125 customers in red (unhealthy), 50 in yellow (neutral), and 25 in green (healthy). Who do you contact first and why (draw the below diagram on a whiteboard if possible)?

No alt text provided for this image

Hiring Manager: You are looking for a proactive answer. Human nature will dictate that we contact the red (in danger) first because we are worried about churn. But, if we take the proactive stance, we have a lot to learn from the green (healthy) customers. Once we have learned what makes them successful, then and only then, we should contact the red. We will then have best practices and action items to share with them. 

Exercise 4 

You are now onboarded and ready to roll. You are starting your day and have these five things on your plate. How are you going to prioritize them:

  • You have an enterprise-level customer having a technical issue that is hurting their ability to use your product.
  • You have 10 unread Zendesk tickets.
  • You have an EBR that you need to deliver in 7 days.
  • You have a new customer that you need to onboard.
  • You have to get your OKRs updated for a meeting that is happening the next day.

What do you do first?

Hiring Manager: There are a few things that you are looking for. 

  • Can the candidate critically think their way through this, and will they ask clarifying questions? They mustn’t spend too much time on this. This should take around 3 minutes to talk through. 
  • There are many ways to answer this question correctly, and there is mostly no wrong or right way. Ideally, they’d address the technical issue first, skim through Zendesk to see if there’s anything else bubbling up that’s urgent, then move on to getting the onboarding started. 
  • Generally, candidates prioritize the EBR (executive business review) last because they have seven days. I always ask a follow-up question around what data would they include in their EBR to double-check that they know what it is. Yes, I have had candidates prioritize this without knowing what an EBR is and without asking what it is. 
  • The same for OKRs. Candidates will occasionally prioritize OKRs pretty high on the list but not know what OKRs are (objective key results). But, depending on what projects you are working on, you could possibly get an extension on your deadline. 

Step 3: 2nd and final rounds. Yep, they have to come back one more time. 

They’ve wowed you and your team, and now it’s onward to the final rounds. Some people aim to get everything done one day, but I believe that having exposure to your candidate on different days and different scenarios is important.

The dating analogy doesn’t work perfectly here because you most likely wouldn’t propose a serious relationship with someone on the 2nd date. Still, at this phase of interviews, you are both generally serious about each other and are looking to make a long-term commitment.

During this final round, I always ask for a presentation to be conducted (it’s only a small portion of the final interview, but very important and what I will focus on for this step).

What I am looking for is that this individual is able to prep a presentation, knows enough about our product, can command a room, think on the fly, is likable, and still has that initial wow factor that we all fell in love with on the first round.

How I typically go about this:

Set up a panel of about 5-7 individuals (small enough to not overwhelm the candidate too much, but big enough to see how they present under a tad bit of pressure). The presentation should be around 15 minutes and allow for an additional 15 minutes for questions. Each person that sits on the panel should ask questions as if they were the customer. Throw the candidate some curveballs and see how well they think on the fly. An example of a presentation scenario that I’ve historically used is:

Presentation Scenario 

  • We just signed a large and strategic customer. There is plenty of growth potential within this account, so building a strong relationship out of the gate will be necessary. Customer Success owns the relationship after the sale has closed. We are responsible for onboarding, implementation, and ongoing relationship health. Please provide a presentation as you would to our new customer with the following details:
  • What is your role in their onboarding process, and how will you add value?
  • What features of our product will be most beneficial giving their workflow?
  • How are you going to partner with them throughout the life of their relationship?
  • Anything else that would help the panel understand how you approach Customer Success and nurture the customer relationships?

It might feel like an impossible task to find the perfect fit for your first customer success role. But believe me, it’s all well worth your time and attention.

At the end of the day, your first Customer Success Manager will directly impact your customers and team’s health and happiness. They’ll also be the leaders for CSMs to come.