How to Hire a Customer Support Team for Your Startup

Charles Sustaita
Charles Sustaita

Whether you’re B2B, SaaS, B2C, or any other type of company, you may have reached the point where you’ve determined that you need to hire another person to build out your support team.

If you’re looking for information on “When you should hire another person,” check out The Customer Support Handbook.

Similar to many growing startups, your resources may be limited. Here are some efficient ways to help reduce the impact of hiring and to increase the number of qualified applicants:

Round 1: Make people fill out an application

Make them fill out an application! “But, Charles, wait, applications can be boring and we don’t want to discourage people from working at our company.” Make the application exciting! Also, you DO want to discourage the lazy from applying. Do you want to hire people who are not excited to work for your company?

What really makes them want to work for your company? They could be on a spree applying for jobs at every company within 15 miles. Sending a cover letter and résumé to jobs@yourcompany.com is an easy way for the applicants to pile up.

You can use a custom HTML form or something simple, like Wufoo, to create an application you can host on your website.

What are the benefits?

  1. An application will immediately weed out serial applicants.
  2. An application allows you to showcase the personality of the company so the applicant gets a feel for who you are and what you’re about (aside from your About page).
  3. If you include thoughtful, personality-filled questions, it allows the hiring team to get a better idea of who the applicant is and what type of personality they have.

What questions should you ask on the application?

Include the basics (if applicable):

  1. Name
  2. Phone number
  3. Email address
  4. Where do you live?
  5. Social media, personal website, and portfolio URLs
  6. Are you legally authorized to work in [your country]?

Spice it up:

  1. “What are your Jedi skills?”
  2. “Tell us something impressive that you accomplished.”
  3. “If you had a lightsaber, what color would it be?” (to which the ONLY correct answer is “blue”)
  4. “Tell us a joke that will make us laugh (if you can).”
  5. “What gets you out of bed in the morning?”
  6. “Why [your company name]? Use 140 characters or less.”

Round 2: YouTube challenge!

Once the applications begin to pile up, choose the people who meet your requirements, who display individual personality, and who could possibly complement the personality of your company.

A YouTube challenge may further establish the personality of your company, but it could also weed out a portion of those who don’t want to go above and beyond to work for you. It also allows the applicant to showcase their creativity.

Customer support folks need to be able to display their personality, should be able to communicate effectively, and should be somewhat savvy with technology.

Ready for the challenge? Create a 90-second video: 45 seconds about what [your company] does and 45 seconds about why you should hire them.

Round 3: Sample questions

Send them a short list of hypothetical scenarios to respond to. Frame it as though they have the job and they’re responding to a customer via a phone call, a chat, or an email.

Don’t hold back. Make them as technical as you want or as simple as you want. The goal is to determine:

  1. How well can they think on their feet.
  2. How well they can rely on existing, internal resources or outside resources.
  3. How creative they can be.
  4. Their customer interaction style.

Round 4: Phone screen

Use their hypothetical scenario responses from Round 3 to probe them for more information about why they chose to respond the way they did and how they went about thinking about responding.

You can also use the phone screen to further determine personality and job fit.


  1. Be boring. You took so much time to put together probably the most exciting job application process they’ve ever experienced, so make sure you’re as cheerful and excited to talk to them as they are to talk to you.
  2. Ask boring questions. Make it a point to state your goal(s) for the phone screen to the applicant.
  3. Set the wrong tone. You want to be playful, funny, and welcoming, but remember to set the right tone so they know the phone screen isn’t a drink at the bar with an old friend; it’s still a job interview.

Round 5: In-person interview

The time has come! Take them for a tour of the office or the work space, offer them water/coffee/tea/etc., make them comfortable, then warn them that things are about to get serious.

Ask them awesome questions:

  • “If I give you a million dollars to start your own business, what would you do?”
  • “What’s your favorite app right now?”
  • “Tell me about a time you really messed up something and what you did to fix it.”
  • “Explain how the Internet works to your grandmother.”

Round 6: Invite them to breakfast, to lunch, or to a happy hour

You’re interviewing them as much as they’re interviewing your company, so it’s important for the applicants to interact with people in other teams or other departments so they’re comfortable with your team. Position fit is one thing, culture fit is another.

At this point, they could turn you down as much as you could turn them down.

Round 7: Tie breaker (optional)

If you’re torn between more than one candidate, put it to a larger vote with everyone who interviewed the applicants. If the entire company interviewed the applicant, even better.

Gather everyone for a thumbs up/thumbs down voting session. Establish a safe, open environment for those involved, openly chat about the applicant(s), and begin voting.

Be objective:

  • Are they a good position fit?
  • Are they a good culture fit?
  • Would you trust that person alone in a room with your most valued customer?

Be real:

  • Does it "feel right"?
  • Are you hiring them because they’re the best out of the group of applicants but not the BEST person you want? If so, reassess or start over.
  • Do they bring something to the table that no one else has?


Negative votes carry more weight than positive votes. One thumb up equals +1 point. Two thumbs up equals +2 points. Two thumbs down equals –4 points. Remember, if someone votes negatively, this is indicative of a problem.

What else does voting do? It introduces different points of view from different team members in a safe space. The conversation you had with an applicant may have been amazing, but there could have been a red flag in the conversation your colleague had with an applicant because of a question that you never thought to ask.

The person with the most positive votes wins. If the vote is teetering on positive/negative, consider it a negative vote. If you have to convince yourself to hire someone, it’s not a good choice. It’s better to start over now than it is to start over in 6 months.