TBH: Some days it sorta felt like this.

This year we raised prices for our oldest customers.

  • It was really hard (for tech, support, leadership)
  • We survived (as teams, as a product)
  • It was the right decision
  • It was really hard

Choosing to adjust pricing for legacy customers is a hard, and emotional decision. It is one that should never be taken lightly. These people were your original crew — your first allies — and the reason you’re here now. They deserve the upmost respect for this history. …


So, here’s the thing. I know a good bit about Customer Support — but I haven’t been here long. Just 4 years ago I was working my way up the ladder in corporate Healthcare. Customer Support excited me, and I knew I had some transferrable skills, but I wasn’t totally sure how to market myself.

When changing career paths, it’s often difficult to take the skills and experience you have, and apply them to a different industry, and different structure and a new ideal of a “perfect candidate.” Below are 4 tips to up-sell yourself into your new career.

Focus on the unteachable skills

When…


Building features like magic stuff.

For a long time we did feature releases like this:

  • We took an idea, or a customer suggestion
  • We got really excited about it
  • We went heads down for days, weeks, months building the perfect setup
  • We wrote perfect help articles
  • We created education and sent out update emails
  • And we waited, with baited breath

And sometimes people loved the changes. But a lot of times they didn’t. Or, it was okay but not exactly right.

There was nothing wrong with our team or the tools we were building, the problem was in our process.

The problem was our timing and when we solicited feedback. We spent months building out features, without asking the customers for direction.

We were…


This is not the cup of coffee I had at 5am this morning.

At 5am this morning I was standing at the counter, eyes half open, trying to figure out if the hotel staff had replaced the coffee for the in-room coffee maker. While rummaging in the 3 or 4 places I’ve seen them leave it before, it suddenly hit me —

Is this what our customers feel, when they log in and see tiny changes in our system?

I’m rounding out my 3rd week in the same hotel. …


3.5 years ago when I first started at Recruiterbox we had a problem to solve. Our Happiness and Engineering/Product team were 8,500 miles and 13.5 timezone hours apart. They worked in an office. We worked remotely. We weren’t really sure how to work together. We started with a simple daily call, to keep on track about what was happening.

I first wrote about this daily call in March of 2016. More than 2 years ago — but to say this transformed our relationship would be an enormous understatement. …


Not my car. Not my trees.

I’ve been working remotely for 3.5 years, and have moved a few times.

Moving while working remotely is incredibly different than moving while working from a “I leave my house every day and go to an office” job. It’s messier. And stressful-er. And difficult-er.

Last Summer I moved out of a rental, and into my parents house. Their house had been on the market, with zero offers, for 2.5 years. They needed to move out of town, and needed someone to be in the house. 5 hours after I finished moving into their house, they got a full price offer…


For real. But I like winter.

A while ago, I wrote about Why I changed how I apologize to Customers. At this time, I had just broken up with the phrase “We Apologize” for a more human “I am sorry.”

I love human apologies but I have recently started to wonder — what if I’m actually not sorry?

In a customer facing world it often feels like it is our job to apologize for everyone else and for our product.

  • I’m sorry the product doesn’t have that feature just yet…
  • I’m sorry this bug is preventing you from completing that task…
  • I’m sorry it’s taken us…


When people find out that I work remotely, the most common question they ask is:

“How do you stay motivated to do work, being at home?”

My typical answer is that if your butt being in your chair at your job in a building with your other coworkers is your main motivation to get work done, then you may need to rethink your career.

In all honesty, I don’t typically have a problem with motivation most days. My biggest problem is actually in stopping working.

  • In not letting work be my entire life.
  • In realizing that the problems today will still exist tomorrow.
  • In closing my computer at the end of…


Spoiler alert — communication and relationships are hard.

Last month I joined the Support Breakfast podcast to talk about building bridges — or how you bridge gaps between Support and the people on your team who fix the bugs in your product. (You can check out the full podcast here, and subscribe — they’re really awesome people!)

When I first picked to topic, I felt fairly confident in our team’s relationships — we communicate well, get things done, and are fairly efficiently bridging timezone, distance, knowledge and language barriers.

But…when I stopped and actually spent time thinking about it while…


Would we make better decisions if we knew it was okay to fail?

Last month, our team switched help desk systems. This decision would change our workflows, processes and day to day. The change was the most impactful for my team directly, but it also had a ripple effect to the whole company. In short: it was big.

I found myself in a decision paralysis. Once I had honed in on what we were after, all of the options were good, but I couldn’t get past that to decide which one was the best. Which one was THE answer.

My…

Chelsea Elyse

Fan of random pictures, sock knitting and delicious food. A chronic list maker, a writer and lover of remote work. @recruiterbox Customer Happiness & Success.

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