Kaylin Bailey

Kaylin Bailey

This week, I caught up with the brilliant Kaylin Bailey

Kaylin is Director of Customer Support over at Illuminate Education, which provides tools for K-12 educators with the mission to increase student achievement and ensure kids are graduating college-and-career ready. Kaylin has been with Illuminate for four years, and has been in leadership for almost two.

Hi Kaylin!  Thanks so much for spending time with me today.  First, how did you get in to Customer Support as a career?

I am so excited to chat with you!

I started my support career as a Customer Happiness Agent at GoFundMe.  I had been in the service industry (waiting tables) for 4 years previously while in college, and support seemed like a natural fit with this experience.

How did you make the move to leadership?

I was promoted into leadership internally at my second company where I was a support agent (Illuminate Education). My VP thought that I would be a great fit to fill in for a team lead’s maternity leave and I only agreed to do it on a temporary basis. Before I moved into support leadership I was really not sure that it was the path I wanted to go down (I was convinced that I wanted to work on the UX team). 

I completed my time in the temporary team lead role, and just as it was ending another team lead left on a temporary basis so I took over for that team. Somewhere through this time I fell in love with my role and decided that support leadership was a path that I wanted to take (shoutout to Matt Dale for believing in me!). When my second round as temporary team lead was completed I was moved into a permanent support leadership role as a Director.

I fell in love with my role

Not a straightforward step, then!  Were there any particular challenges in those early days?

Since my first two experiences in leadership were temporarily covering for team lead that was returning, I found it challenging to know when to change a process the team was working with and when to maintain things as they were. I ultimately found that as long as a change was for the better of the team it was worth doing even when I was in a temporary role.

Another big challenge for me in the beginning was navigating from being an equal to being a lead, particularly to many friends that I had worked with for 2+ years in the same role. This part got easier with time and with the discovery of Radical Candor by Kim Scott.  

A big challenge for me in the beginning was navigating from being an equal to being a lead

And have there been other hurdles since then?

My biggest challenge has been that our company has grown rapidly over the last 2 years through big mergers. Supporting the team through a ton of change has taken a very conscious rollout of new processes and structure.

Getting quality time with the whole team can also be really challenging – as I am sure many in customer support would agree. Our team’s number one priority is to cover support interactions, which are always coming in! Doing an all-hands meeting is not as easy or possible as it is for most other departments.

Getting quality time with the whole team can also be really challenging

What makes a good CS leader, do you think?

Listening to and truly caring about the people on your team is so important! If you have a base of communication and trust, teams can overcome most hurdles that are thrown at them. I also try to live Radical Candor with my team everyday – feedback is so vital for everyone on a team (including my team giving me feedback).

How do you use metrics and measures?

We have KPI’s for our support team that relate to phone calls and tickets (the current channels that the team uses). Some of these include number or solves, time to resolution, duration on the phone etc. 

A couple of specific metrics that I find most useful are first reply time (which helps to determine if we have enough agents) and number of agent touches in a ticket before resolution (the smaller this number the more confidence I have in both our help documentation and the individual agent’s knowledge of the product that they are supporting). Another way that we measure an agent’s level of knowledge of the product is their ability to do an internal training on a module. Once they can successfully do an internal training they would be considered an expert in that area.

While metrics are a very important piece of measuring success in support, it is always important to know who the metrics are going to and also to acknowledge that not all success can be measured in numbers. Knowing the end goal of what you are going to do with the metrics you’re pulling is essential as well.

Not all success can be measured in numbers

Is leadership different to how you thought it might be?

Leadership is totally different than I thought it would be! Going in, I thought it would be quite similar to a support agent role, but with some added responsibilities. My biggest concern (and the reason I initially did not want to be in leadership) was that I had heard from so many friends that were managers at other companies that they did not like their jobs and felt like they were constantly having to tell people what to do. The reality for me was that my team is amazing and I did not share the same experience that my friends had. I quickly learned how to make feedback a natural conversation rather than always having to be a hard topic. 

I was also really wrong thinking that my leadership role would look anything like a support agent. While I was always aware of the queue and jumping in to help as a backfill, I had to adapt to looking at the big picture (what is coming in the next year? How can I improve the process? How will this affect all the other teams at the company?) instead of the smaller picture (Are my numbers good? Is my team doing ok?).

I also did not realize how much of an adjustment it would be to measure my success without the metrics I was so used to looking at (I was the type of person that was always aware of the leaderboard and where I fell on it). 

I did not realize how much of an adjustment it would be to measure my success without the metrics I was so used to looking at

Do you have any favourite resources?

Support Driven! It is so amazing to have a community that I can learn from, add to and ask questions of when I need to. I also really love the help scout blog and ask a manager.

And the one I seem to have become known for… how do you sign off an email?


Thanks, Kaylin!  You’re right, getting the whole team together is a challenge, when everyone is so heads-down in the queue.  It’s a challenge worth figuring out, though, because face time is so important to building smooth working relationships.

More next week from another inspirational Customer Support Leader!