Or don't ask, what do I know about what you're thinking.

Well, many reading this blog may be curious about my professional career. Perhaps it can provide context to my thoughts and opinions. If that interests you, read on! Otherwise feel free to find something more to your liking.


So I have worked at Rain since January of 2019, but this has been my second time there. I also spent a year there from 2016-2017. First I'll talk a bit about Rain itself, then about my various roles there.

Rain Retail is a company that provides a Point of Sale and E-Commerce solution for small businesses. We're modern, web based, and expanding rapidly. We typically focus on a few niche industries, but have customers all over the spectrum. You can learn a bit more from Greg:

Rain Retail Software Intro Video

Thanks Greg, always a pleasure.

My Start

So I joined Rain for the first time in May of 2016 as an account manager. I took on accounts after they signed up to help them get trained and live on their new website and point of sale. When I joined, we had about 40 employees, so it felt really small and scrappy, which was awesome.

I really enjoyed doing this work, and miss it often. Working with customers while they were most excited about the product was a lot of fun. I also feel that I learned more about the small business retail space during this time than any other.

After working as an account manager for about 6 months, I was asked to take on a new initiative starting a customer success department. We were growing, and our customers needed someone to make sure their experience with our company from sales through to support was positive.

Working in customer success gave me unique insight into the customer journey. I feel that combining my time doing Account Management and Customer Success, it helped solidify my empathy with the customer which has probably benefited me as a product manager more than anything.

I am sure this will be expounded into another post very soon, but I feel that product management should be as much of a customer facing role as customer support. A product manager that is disconnected from the customer is one who will make very poor decisions on the customer's behalf.

The Prodigal Son

In May of 2017, I was offered a job in sales by my dad's business partner. Sales had always intrigued me, so I decided to give it a shot. I spent the next 6 months doing outside sales. It was....rough.

So I made it my goal to move away from sales as quickly as possible. I worked over into a project management role, which then turned into a product role. I learned a lot at this time, making sure I never ended up in sales again.

The Return

At the beginning of 2019, my old contacts at Rain learned I had moved into a product role and reached out. They were growing their product team and asked me to join it.

There have been a lot of lessons learned since then, and lots of exciting things worked on. I am sure I will have much more to share!