Customer Success and How I Got Here


When I was little and when people asked what I wanted to be, the answer was President (or rather Prisident, I was a horrible speller).  As I got older, I shifted towards wanting to do something related to science.  I wasn’t particularly gifted in science, but I thought it was more interesting than the other subjects.  My senior year of high school I took AP Environmental Science and was hooked.  It was such a tangible science.  I was learning about things I interacted with daily and I loved it.

I ended up switching my major and diving into Environmental Science (I got accepted as a biological sciences major).  It turned out there were 2 paths in Environmental Sciences…Social or Sciences.  My advisor suggested I take Sciences because it’s what everyone does.  So that’s what  I did.

While I enjoyed what I was learning, I never really connected.  My classes were interesting, but I struggled sometimes.  I worked in an entomology lab, did a great job of taking care of my colony, but ended up getting fired (because of transportation issues, but I wasn’t too disappointed).

I realized that the path I was on, just wasn’t for me.  My classes and job were more about science and less about the interactions, the thing that really excited me about Environmental Science.

Unfortunately, this realization came when I was a little over 3/4 of the way through college. I went to my advisor and her suggestion was to just stick it out.  So I did and I got my BS in Environmental Sciences.

During that stick it out period, I needed a job.  My ex-boyfriend’s mom had opened a clothing boutique and I began helping out.  Helping out turned into part-time work.  Part-time work turned into full-time work.  Full-time work turned into the opportunity to own a store.

The boutique was in a small town and without a great reputation we wouldn’t survive.  We treated every interaction as the opportunity to create a genuine and memorable experience.  My job was to interact with people, all the while being friendly and helpful.  I truly enjoyed it.

It turned out working in retail was so much more fulfilling than getting a college degree.

After helping run the store for a few years, I wanted to move to LA and open a store near UCLA.  The plan was for me to co-own and run the store while my ex-boyfriend’s mom would finance it.

We looked at a few locations, but after running the numbers my plans for opening a store in LA were over.  Rent was way more expensive and the financial gamble was too much.

That left me with a tough decision to make.

Open a store somewhere besides LA or leave the store completely.

I decided to leave the store completely.  I wanted to grow in my career and while owning a small business is a great goal, there wasn’t much difference between what I was already doing and what I’d be doing as an owner.

I wasn’t exactly sure what I wanted to do.  I knew that it wasn’t environmental science and that I loved interacting with people.

I started searching for a customer service or admin job.

I got hired as a Payroll Specialist at Paychex.

I learned a lot, but it was a little too corporate for me.  The conversations I had were transactional and I didn’t really get to connect with the customers that I was helping.

Since I wasn’t entirely happy in my job and I was still living at home, not in LA where I wanted to be, I decided to apply to 1 job in LA.  If I got it I’d move.

Surprise, surprise…I got it.

I was officially a Customer Service Rep. (and eventually a Customer Success Rep)

I was constantly interacting with people. I was helping customers solve their problems.  I was interacting with my team, collaborating, learning, and teaching.

I found a job that satisfied my need for meaningful interactions and has plenty of career growth.  I’m happy and can’t imagine doing anything else.









Mentor Everywhere

I’m officially a mentee for the first time.

I found out about the mentor everywhere program on the support driven slack (an amazing network/resource for anyone in a customer support/success/service role).

I submitted an application to be in the first cohort and crossed my fingers.  I’m pretty confident in my CS skills (and have support driven for help), but I really didn’t have any resources for helping grow in other areas.

I got an email notification that I was selected to be in the first cohort and was so excited!

I’ve never had a mentor, so I wasn’t sure what to expect, but I knew it’d be good stuff.

First, Chris reached out and we did a quick e-meeting/introduction.

I did a bit of poking around and found this on his company’s website:


His previous experience was great, but really the last sentence is what convinced me the automattic team did a great job in matching me with a mentor.

Tacos.  Enough said.

In all seriousness though, support, operations, and leadership are things I want in my career and Chris’ experience falls directly in line with that.

In our intro emails we also set up today to be our first official meeting.

We used zoom and of course my camera decided that it really wanted to be a camera from 2002 and I was super fuzzy during the conversation.  We worked through it though and my tacos conclusion turned out to be true…our conversation flowed pretty easily.

We talked about our history and what we hope will happen during the mentorship.

Here’s a quick summary:

My overall goal for the 6-month program

To be on a path that leads directly to management/leadership.

In order to achieve that goal we’re going to focus on

Learning and nurturing management and leadership skills.

To make sure we stay on track

We’re meeting every other week and I’m blogging about the experience here 🙂

Chris had some great advice on leadership.  My favorite was:

You’re going to make mistakes as a manager, but as long as you learn from them, you’re good.

I’m pretty sure I’m paraphrasing, but that was the sentiment.

Other great tips were:

  • When giving feedback, it’s good to remember that you respect your employees.  Part of respecting them means giving honest feedback.
  • Make sure you’re serving your team.  As a leader, it’s your job to make sure they feel supported.
  • Leadership books are great, but there’s no substitute for life experience.
  • Step up and do the things that need to be done – this was an answer about the transition from support to CEO.  Helping out and staying interested, it counts.


So, as you can tell, we’ve already got some great plans.  I’m looking forward to developing this relationship as time goes on and seeing the impact it has.

I’ll post more as it happens 🙂





Hi, I’m Diane!


This is the full version of the photo I use for profile pictures.  Cropping our the sunglasses makes it so much more professional.

Today, I bit the bullet, paid for a domain, and decided to start a blog.

I’m a millennial, so of course, I’ve blogged on Myspace and blogger…this was many moons ago and usually fueled by a break up or some other emo thing.

I’d been thinking about blogging again, but I didn’t really have a purpose or clear goal in mind.  I still don’t really, but now I have a place to put my thoughts and ideas…which I guess is a purpose…kinda.

I want this blog to be a reflection of what’s going on with me…so here’s a little bit more about me:

I live in Santa Monica…with my awesome boyfriend.

I work in Customer Success…and start a new job on Monday.

I like hiking with my friends…but don’t get up early for it.

I like to stay active…by taking spin or lifting weights.

Obviously, there’s more…but that’s what other posts are for!