How to Make The Best First Hire for Customer Success

You’ve closed some deals. Cash is finally coming in. So, let’s keep the foot on the gas! Right?

Well, not exactly. There are a few things you need to get in order before accelerating your shiny new Sales engine. The first being figuring out how to learn from and grow with the clients who got you there: Enter Customer Success.

Now, the first order of business for starting your CS team is making the right first hire, which will be critical in the success of your overall organization beyond just the Sales team. Below are the steps you need to take to ensure you get it right the first time.

Step 1: The Ask

Think hard before starting your search. What is the true expectation of this hire? Specifically, what problem(s) are you bringing them in to solve?

Will they be doing only some of these? All of these?

  • Client management
  • Process development
  • Product training
  • Churn mitigation
  • Revenue expansion
  • Team hiring

The outcome of that analysis will set the tone for your search. Specifically, do we shoot more senior for a Head of Customer Success or junior with a Customer Success Manager? More often than not, you’ll want to bring in an individual who’s done it before that and can build it right, not just someone who can handle requests as they come. This hire will undoubtedly branch to additional team members over time, so process and experience will have a tremendous ripple effect on the team’s work ethic and culture.

Step 2: The Must Haves

As badly as you may need to make this hire, don’t let it make you sloppy. You’re bringing in someone to take a lot off of your plate, but valuing the wrong skills can create more work for you in the long run.

What does this candidate need to have because it’s essential to your business? Past experience in some (or all) of the following:

  • Customer Success
  • SaaS
  • Your industry
  • Management
  • A closing or contract management role
  • Working with clients ranging from SMB to Enterprise

Step 3: The Archetype

Which characteristics are you looking for when molding the perfect person for Customer Success? These are the four that myself and other Heads of CS have found to be the most successful:

Entrepreneurial Spirit

Entrepreneurs understand that great things come from humble beginnings. At this stage, your product almost certainly hasn’t earned the elusive title of “Enterprise-ready.” Your CS team will be keeping the product afloat as you iterate. They’re an ambassador for the product, the face of your company to the customer. An ability to sell their own self, the company, and the customer experience can make the difference between retention and churn.

Mental Agility

Can the candidate think on their feet? Are they able to manage different projects and timelines without getting overwhelmed or dropping the ball? How do they organize their tasks? How do they balance gut instincts and experience? Customer Success involves very little scripting, as the target is constantly moving. New clients, new product features and new processes will be challenging the customer experience you’re offering, both positively and negatively.

Consultative Mindset

Good luck telling a client “You are not special. You are not a beautiful or unique snowflake.” That only works in Fight Club or Full Metal Jacket.

Every client has different mix of needs, goals, personnel and use case. It’s the job of Customer Success to satisfy those with a tailor-made strategy that can be executed within the confines of your product’s capabilities. This isn’t a skill you’re born with; it’s learned from numerous client encounters. A Head of Customer Success who can’t draw upon past experience is bringing very little to the table.

A “Get Stuff Done” Attitude

Amazon’s Leadership Principles call this a “bias for action.” Look for someone who can get their hands dirty. No task is beneath them, especially when the job just needs to get done. This person understands the big picture and the effect they have on it.

Look at your own team and product through this lens. Bugs happen. Not every process is automated. Some don’t even exist yet! Starting a CS organization isn’t easy. Find the individual who is up for doing the dirty work because it’ll be better for the company long term.

Step 4: The Interview

Make inquiries that will help you evaluate the candidate based on the Ask, Must Haves and Archetype. Do they seem to be a good match in terms of experience, ability and culture fit? Press them — your clients will. Dive into how they’ve managed client expectations, handled product disasters and the occasional over-promise. Humility is important. We all mess up. Ask them about their mistakes and what they’re proactively doing to prevent them from happening again. CS is the glue that connects each department in your company. Get them to open up about cross-functional work and their ability to manage projects.

Great, now let’s see how they think on their feet.

Case Study (Evaluating Mental Agility and Consultative Mindset)

I run a case study in every Customer Success interview staging a client onboarding. The client needs to launch within a specific time box (e.g.: 2 months) and see value during their short term pilot contract (e.g.: 6 months). The candidate is given very little info on the client, basically what you’d find in a contract (e.g.: license count, contract length, products purchased, etc). Taking a bare bones approach allows you to focus on the candidate’s ability to tackle a problem without having all of the necessary info to succeed. Put their discovery chops under the microscope.

For consideration during this exercise:

  • What clarifying questions do they ask?
  • Do they account for key implementation variables like stakeholders, integrations, data preparation, product training and communications strategy?
  • How does the candidate lay out an implementation timeline that will allow for launch within the time box?

Follow up by asking how they would evaluate the program, especially when making a case for the client to renew.

For consideration during this exercise:

  • How analytical are they?
  • What data do they think would be most useful for the client to see and why?

This hire is the keystone of your retention strategy, which could make or break your company’s long term success. There’s no true silver bullet for hiring Customer Success when it comes to past experience. Focus on your core needs, but keep an open mind along the way. Make your Customer Success team a force to be reckoned with.

Cam Williams is the Head of Customer Success at Healthify. He and his team help organizations achieve more through a combination of technology and training. After getting his start at Amazon, he went on to lead an award-winning client services with Grovo.

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