How to Hire an Amazing Customer Onboarding Specialist

How to Hire an Amazing Customer Onboarding Specialist

Customer onboarding is one of your most important hires. Here’s how to get it right.

We’ve talked a lot about customer onboarding on this blog, and here’s why: it’s one of the most important elements⁠—if not the single most important element⁠—of customer success.

Great onboarding is the difference between a customer logging in once, and never coming back (as 40-60% of software users do), and that same customer sticking around and being a long-term, high-value loyal customer for life.

The role of the onboarding specialist is to take a customer from that very first moment of signup, to the moment of “first success” with your product or service.

A disproportionate amount of customer churn takes place between (1) and (2) above. That’s where customers abandon your product because they get lost, don’t understand something, don’t get value from the product, or simply lose interest.

And that’s where an effective onboarding specialist can make a real difference in your business.

Today, we’re looking at the five key skills to look for in a customer onboarding agent, and how to spot those skills in the application and interviewing process.

You might also find useful:

The Five Most Important Skills in Customer Onboarding

1) Empathy

Empathy gets thrown around a lot in support training, and for good reason: it might be the single most important customer service skill to develop.

To help your customers be happy and successful, it’s important to understand what happiness and success mean to them. And to do that, you have to step into their shoes.

I love the way that Derek Sivers leaned on empathy when building relationships with his customers at CD Baby, which he grew into the premier music website of its day.

If someone would call, saying, “I’d like to talk with someone about selling my music through you,” we’d say, “Sure. I can help. What’s your name? Cool. Got a website? Can I see it? Is that you on the home page there? Very cool. Is that a real Les Paul? Awesome. Here, let me listen to a bit of the music. Nice, I like what you’re doing. Very syncopated. Great groove. Anyway… so… what would you like to know?”

I can tell you from my own experience of being a self-promoting musician for 15 years that it’s SO hard to get anyone to listen to your music. So when someone takes even a couple minutes to listen to you, it’s so touching that you remember it for life.

Every customer service professional⁠—and every entrepreneur⁠—needs to read, re-read and internalize that perspective.

2) Positivity

This is not the kind of positivity you’ll find on inspirational posters of a sunset on the beach.


Eh, okay, probably not.

This kind of positivity doesn’t necessarily refer to your outlook, but to the language that you use.

To understand how powerful positive language is, let’s take a look at some negative language. What do these words really mean?

  • Unfortunately: I’m about to tell you something bad.
  • As you know: I’m putting you in your place, and confirming your worst suspicions.
  • I’m afraid that…: Just like As you know, this one invariably always comes before bad news.

3) Patience

Customer service is not an easy job.

Sometimes, your customers will be angry with you.

Sometimes, your customers will need extra attention to understand things.

Sometimes, things will simply be difficult.

The worst thing you can do in these situations is lose your cool.

Patience not only helps you deliver better service, but one study from the University of Toronto found that being impatient not only impedes our ability to enjoy life, but it makes us worse at doing hard things (like delivering great customer service).

4) Clarity in Communication

Clarity isn’t just important for making your customer feel good.

It can also make a big impact on your bottom line.

What if you could send one less email per support interaction because you didn’t have to clarify anything that your customer didn’t understand the first time?

If you field 300 requests a week (on the low side of an average Groove customer), that’s 15,600 fewer emails sent in a year.

While that example might be a bit extreme, even if you could send 0.25 less emails, on average⁠—a very reasonable expectation⁠—you’d still send 3,900 fewer emails in a year.

That’s not insignificant, and it’s a great argument for practicing crystal-clear communication.

5) Continuous Improvement

I can prove to you that these skills will help you deliver better support to your customers.

But in order to see the proof for yourself in your own business, you need to measure your performance.

Getting metrics-driven is not only an invaluable customer service skill, but it’s the only way to know for certain what kind of impact your efforts to develop better skills are having on your service.

How to Spot These Skills in the Application and Interviewing Process

Sure, it’s easy to write an onboarding specialist job description and list the skills you want.

But will that actually get you the best candidates?

Of course not.

To really attract the best talent, you have to go deeper than that.

Here’s how:

Write a great job posting

If you want commodity customer onboarding agents⁠—that is, warm bodies that will answer questions and not much more⁠—then write a commodity customer onboarding job posting.

But if you want to attract the best customer onboarding employees⁠—the kind who can help you reduce churn, increase retention and move the needle on other important business metrics⁠—you need to write great customer onboarding job descriptions.

3 Steps to an Effective Onboarding Job Posting

1) Choose Your Words Wisely

Notice how at Groove, we look for customer onboarding experts, rather than customer onboarding representatives?

And how we list the tasks that the right candidate will accomplish, rather than do?

The words you use to describe a customer service position are incredibly important. By making it clear that you’re looking for top performers, you stand out among the crowd of businesses looking to hire “reps.” To top performing employees who care about being challenged and successful, that differentiation matters.

Here are a few more examples from some of the top SaaS and eCommerce companies in customer service:

2) Make Your Culture Come Through Clearly

Your culture comes through in everything you do, from your product to your marketing to your customer support.

There’s a good chance, especially if you’re a smaller business, that your culture is a big reason that your customers are choosing to do business with you.

That’s why it’s so important to preserve and maintain that culture, and to make sure that it comes through clearly in your job postings.

We like to include links to our blogs — where we share a lot about our culture — to ensure that applicants have a great understanding of how we work and live.

Buffer requires you to check a box stating that you’ve read two (amazing) books that they live by:

Unbounce wraps some of their job requirements in funny prose to make it clear that they want people with a sense of humor:

Whatever your culture and values are, it’s important to make sure that they come across in your job posting.

3) Make Them Work for It

No, this strategy is not as nefarious as it might sound, and the goal is not to get “free work” from your applicants.

We always ask applicants to complete an assignment before we decide whether to interview them. Here’s the email that Alex, Groove’s CEO, sends:

There are two reasons we do this:

First, it weeds out the “résumé blasters” who apply to any and every job posting without concern for whether or not they (or the job) are the right fit.

Second, it gives us great insight into their customer service skills, more so than any resume or cover letter ever could.

The key here is to ask open-ended questions that show you how an applicant approaches the various challenges they might come up against in their role.

One example for an onboarding role would be: “We’d like to get an idea of how you can clearly explain concepts and processes to customers. Tell us, step-by-step, about something that you shop for online, and how you go about searching, choosing and purchasing it.”

Ask the right interview questions

“What are your three greatest strengths?”

Sound familiar?

Tired, cliche interview questions are dangerous for two reasons: they don’t give you much insight into how qualified a candidate is for the role, and they immediately tell the best candidates that you’re not a great interviewer, and likely not a great fit for them.

Instead, the best customer onboarding interviewers use role-play scenarios to separate the stars—those who have what it takes to deliver amazing customer experiences—from the rest of the pack.

Here’s why:

  1. It’s the only way to truly test for the essential customer service skills

    How can you learn if a candidate has skills like empathy, positivity and patience?

    Certainly not by asking them canned questions about their greatest weaknesses.

    The best way to see if these skills exist are to put the candidate in positions where they’ll need to practice them.

    Which leads to…

  2. It shows you how the candidate handles uncomfortable situations

    Customer onboarding is often uncomfortable.

    But it’s those uncomfortable situations—when customers are angry or upset, or when the agent doesn’t have the answer right away—are when customer loyalty is most on the line.

    Relationships can be won or lost in those interactions that start with uncomfortable circumstances, so you better be damn sure that your onboarding agents can deal with them.

  3. You’ll see exactly what your customers are getting

    You wouldn’t hire a developer or a marketer without looking at their work, would you?

    Then you shouldn’t hire an onboarding agent without seeing the work they can do, either.

    Role-playing in interviews gives you a great glimpse of what your customers will be in for when they send you an email or give you a call with a problem.

Try these three role-play scenarios that will give you a valuable understanding of how your candidate stacks up:

A rude customer


  • “I want a refund, and I want it right now.”
  • Get angry/raise your voice
  • Make unreasonable requests/demands

What you’re looking for: Staying cool is an important skill, especially when customers are angry. Look for empathetic responses (remember, you can be sorry for how a customer feels, even if it’s not your fault) and a calm, level demeanor. Bonus points for employing customer service recovery techniques.

Tip: You’re not trying to be a real jerk (the kind of customer you would fire). This is about recreating those more common situations where an otherwise good customer is simply having a bad day.

Making a customer’s day


Go through any totally routine customer support interaction, and then ask: “How would you make this customer’s day?”

What you’re looking for: You want people who understand the value of taking that extra step to surprise customers. Anything from small touches like handwritten notes or personal “thank you” emails to larger gestures for a bigger wow.

Empowering your customer support team to wow your customers is one thing; you need employees who are willing to take advantage of that.

Understanding a customer issue


“[Feature X] isn’t working for me. I’m not technically savvy enough to know how to take screenshots or record screencasts. I’m getting really frustrated, and I just want it to work. Fix it!”

What you’re looking for: Not every customer will be as technically adept as you are, and you can’t always rely on computer wizardry to help you understand an issue.

There are multiple ways that one could properly approach this issue (e.g., walking the customer very simply and clearly through taking a screenshot, scheduling a call, asking great questions), but what you’re looking for is empathy for a non-technical customer and clarity in conveying exactly how we can get the problem solved.

Learn more about writing great customer service job descriptions.

Keep Training Your Team on the Five Key Skills

It’s not enough to simply hire onboarding specialists with the right skills.

In order to keep your team performing well, your training has to be designed to keep those skills sharp, and improve them over time.

The good news is that this doesn’t have to take a long time.

There are customer service training exercises that take 10-20 minutes (and in some cases, even less) that will help you make big improvements in all five of the essential skills.

1) Show-and-tell

You have interests and hobbies outside of work, right?

So do the people you work with.

There’s a good chance that whatever your particular hobby is, you know a lot more about it than the people around you. They might even find it confusing or intimidating.

One of the most critical parts of being able to communicate clearly is the ability to distill complicated topics into simple, easy-to-understand terms.

Hosting a weekly show-and-tell at your office (or, if you’re a remote team like us, over Skype or a Google Hangout), is a great way for your team to get better at conveying complex ideas—whether they’re about crossword puzzles, travel hacking, knitting, Dungeons & Dragons or whatever else they enjoy doing—to those who might not be familiar with them.

It’s also fantastic for getting to know your co-workers better, and building stronger relationships throughout your entire team.

The exercise: Hold a weekly show-and-tell session.

Each week, a member of the team is assigned to share a 5-10 minute presentation sharing an interest or hobby with the rest of the team.

Skills Developed: Clarity in Communication, Empathy (for those listening)

2) Do the Stranger Challenge

One of the hardest things about doing support is customers being angry or upset with you.

And while the specific techniques for dealing with those situations are easy to learn and use (if you haven’t tried it yet, I highly recommend the HEARD technique used by Disney), the more challenging part of that is simply the fact that’s a highly uncomfortable situation.

Most people aren’t very good at being uncomfortable.

It’s hard to be at our best when we’re not comfortable, but those uncomfortable situations, for support pros, are where we need to be at our best.

So what do we do?

We work on getting comfortable with discomfort.

AppSumo runs a challenge on their site that they call the Stranger Challenge. It involves getting over your fear of failure and discomfort by asking a complete stranger to take a photo with you.

Yes, it seems a bit weird and uncomfortable.

And that’s exactly the point.

Completing the challenge will help you get better at being comfortable with discomfort.

The exercise: Do the Stranger Challenge

Print out a sign like Sumo’s and ask a stranger to take a photo with you.

Skills Developed: Empathy, Positivity, Patience, Continuous Improvement

3) Become More Mindful

If you’ve never tried mindfulness meditation before, it’s important to establish a couple of things:

Firstly, mindfulness meditation has nothing to do with religion or spirituality (unless you want it to). Absolutely nothing. This is probably the one misconception that I had that kept me from trying it for a long time, but I promise: nothing.

Secondly, the benefits are massive, and they’re backed by science. Mindfulness meditation has been shown to do everything from lower stress to making you a more compassionate and empathetic person (both benefits that anyone doing support could get a lot from).

Mindfulness meditation is a great way to get better at reacting to stress and not being overwhelmed by the seemingly never-ending flow of support emails.

Personally, I love Headspace, a simple app that teaches you meditation in 10 minutes a day, and I think it’s a great place to start for just about anyone.

The exercise: Take 10

Sign up for a free Headspace account, and complete the Take 10 program: 10 days of guided meditation, in only 10 minutes each day.

Skills Developed: Empathy, Positivity, Patience

4) Give Genuine Appreciation

Dale Carnegie, in How to Win Friends and Influence People, praised appreciation as food for the soul.

In our interpersonal relations we should never forget that all our associates are human beings and hunger for appreciation. It is the legal tender that all souls enjoy.

Dale Carnegie, How to Win Friends and Influence People

It’s a haunting phrase that’s stuck with me since the first time I read it.

But the power of a real thank you goes way beyond making someone else feel good.

That power was tested in a 2010 study by researchers from the Universities of Pennsylvania and North Carolina, when behavioral scientists Francesca Gino and Adam Grant set out to see what the impact of receiving gratitude can be on someone’s behavior.

In the study, participants were asked to give feedback on a fictional student’s (“Eric”) cover letter.

After the feedback was received, the participants got a reply asking for feedback on a second cover letter.

This is where things get interesting.

Half of the participants got a straight, to-the-point email with the second request, and the other half got an email expressing gratitude for completing the first review.

Here are the actual emails that were used:

The results?

32% of the “No Gratitude” group provided feedback on the second cover letter, while 66% of the “Gratitude” group—more than double—sent more feedback.

That’s not a small difference.

But the researchers took it a step further.

The day after completing the study (or so they thought), participants got yet another request for help. This time, from a different fictional student (“Steven”).

What happened was fascinating: 25% of the original “No Gratitude” group offered to help Steven, while 55%—again, more than double—of the original “Gratitude” group offered to help.

Remember, they had never heard of Steven before: the effects of receiving gratitude carried over and still made them more likely to help the following day.

Receiving gratitude doesn’t just change the way we think and feel; it changes the way we behave for the better.

In business, appreciation can help you build deeper relationships with your customers, and make them more likely to do what you ask of them, whether that means staying with you, buying more or referring others.

Appreciation is a powerful tool in any interaction, as long as it’s genuine.

The exercise: Say Thank You

Pick 10 customers at random and send them a sincere, personal thank you that shows them why you’re grateful for their business.

Repeat once a week, forever.

Skills Developed: Empathy, Positivity

5) Take an Acting Class

If it seems like a lot of these exercises focus on empathy, that’s because it’s perhaps the single most important skill you can develop no matter what your job is.

Empathy is about standing in someone else’s shoes, feeling with his or her heart, seeing with his or her eyes. Not only is empathy hard to outsource and automate, but it makes the world a better place.

Daniel Pink

But if there’s any job where empathy is 100% mission critical, it’s customer success.

There’s nothing in the world that calls on you to step into someone else’s shoes more than acting. And the good news is that even if you don’t have aspirations to be the next Leonardo DiCaprio or Meryl Streep, you can still take classes to help you achieve their empathetic superpowers.

The exercise: Take an acting class

Search for acting classes in your area. Or, sign up for an online acting class (here’s one taught by Dustin Hoffman that includes practice with fellow students and getting feedback).

Skills Developed: Empathy

Make Your Next Onboarding Hire a Successful One

Hiring customer onboarding specialists is a big and exciting step for your business.

It means that you’ve delivered enough value to enough prospects that they’re signing up for your product.

And for that, you should be proud.

Use this guide to find and hire a customer onboarding expert that will help you delight your customers and grow your business.

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