I get asked 2 questions frequently and that makes me realize I should just write out answers to them so that I can better scale myself.

The two questions are:

  1. Why did you leave Shopify?
  2. Why did you leave Notion? Or, if they know I was fired, they ask, why did you get fired?

Why did you leave Shopify?

Losing my Friends.

I had a great group of close friends that I worked with at Shopify. I consider it a group of 5 of us and most of us were working 12+ days 5-7 days a week, depending on the week. I feel like I learned so much because we learned so much; it wasn't so much that I was a great sales rep... it was more that #1 we would put in the hours that no one else would put in and #2 not only were we iterating ourselves and learning fast, we were iterating with each other and learning extremely quickly.

Near the end of 2017, beginning of 2018, all of my friends had left (one did eventually return but that's not the point). I was by myself just chilling.

A) Before, when we (the sales team) had the cards stacked against us, I could look around at my buddies and we were ready to dig in and fight to the end. But, with them gone, I sort of lost a strong "why" I had organically developed during my time at Shopify.

It was really lonely and I felt like I didn't have as strong a reason to stay there anymore. B) From an ego point of view, my friends, who I all considered very smart, they all left Shopify. So there I was, someone who thinks he's smart but all his other smart friends had left.

So I do think there was some ego involved to. Why am I still here if they have all left? #MemeticTheory?

Burned Out

I was arguably not in the best mental state near the end of my time at Shopify, which I would consider from November 2017 - August 2018.

I personally thought the sales team had pretty much thrown in the towel for hitting our numbers in September of 2017, meanwhile we still had all of September AND Q4. So I felt like I had to be like Leonitis and put the team on my back so that we could hit our numbers.

Then my friends left.

And, since June 2016, I'd pretty much been working full days, nonstop up until that point. I remember sleeping at the office so that I could do calls with Singapore merchants at 12:30 am but then also be able to make a 6 am call with the UK. I was burning the candle at both ends of the stick.

Differences in opinions

I love Shopify and I am forever grateful for my time there. It was awesome and it will definitely be hard to top. I am a big fan of the people I worked with and work for. I especially really like Shopify's top management: Tobi, Harley.

But, near the end of my time at Shopify, I started to feel not so great about the direction I perceived Shopify Plus Sales was taking. This might have been a maturity thing. I know for certain I really liked the way Shopify Plus Sales had been and was holding onto that and not wanting things to change. But, also, some decisions were made that I didn't feel like I would want my name beside. #NewspaperTest

Further, things to me seemed to become more corporate and added more processes/systems. It makes sense — the company was growing and getting bigger — but I also didn't think they should add processes just to add processes. And I found people who were brought in seemed to be more looking out for themselves. I think it's just a function of getting bigger, becoming corporate, etc.

Put on team I asked to not to be apart of

In 2017, I was the top sales rep. I knew that in 2018 they were going to initiate segments; vs. before it was the wild west. Anyways, I specifically asked to be not on a particular team.

In 2018, they put me on that particular team. 🙃 In hindsight, I think they needed me on that team to sort of "subsidize" the team while every one else was going through transitions. However, in the mental state I was in, it made me very pissed.

In hindsight, I probably would not have left Shopify knowing what I know now.

With that being said, that's the funny thing about hindsight, you only know it after the fact! ;)

AND Shopify is a great company! I highly recommend it to people. I believe in what they are doing from a product offering standpoint. And, at least while I was there, I found they viewed employees as complete humans rather than just employees who happen to work there from 9-5.

I do recommend anyone considering them ponder why they want to work there to make sure they aren't getting into it for the wrong reasons — read here — but, generally speaking, they are an amazing company!

Why did you get fired from Notion?

Ah yes, Notion.

Not the right skill set (at the time) / not making tradeoffs / not doing proper expectation setting

Shopify was nice because when I arrived there was a decent sales playbook set up AND there were others in the same role as me who I could bounce ideas off of.

When I went to Notion, there was no formalized sales process. And I was n = 1.

Notion had been doing super well before I arrived. And I was basically tasked with setting up formalized sales process AND also closing deals.

So, I didn't really have the skill set to set up a formalized sales process AND, at the same time, I was also tasked with closing deals. And I think because of how well they (Notion) had done organically (they had contracts with some major corporate clients), they thought it would be an easy close for me.

Not enough time

To add onto the above thought, I only was working in sales at Notion for like 1.8 months before I was let go.

For the first month, at least, Notion really wanted me to learn more about the product and how to use it, so they got me working support for at least the first month.

Then, when we came back from our Offsite in Colorado and I was to begin selling, something ahppened so they asked if I could be put back onto Support now and again. I don't know about you but 1.8 months to close major deals — heck even give me 2 months — is not really a long time. I probably did not do a good job of expectation setting before I arrived.

My attitude

I have anxiety. I get worried about things. And I bring those things up. I bring those things up because I care. I want whoever I'm working for and with, I want us to survive and thrive. So it's definitely from a place of good intentions. With that being said, I could see how this might come across as complaining or annoying. If every time you talk to me I respond by saying, "I'm worried about this and this." I could definitely see how I wouldn't be a fun person to be around.

Not only that, I would say I was in a place of existential angst while there. I was asking myself and others big questions while I was there.

Pioneers get slaughtered, and the settlers prosper.

Written: November 12, 2020

PLZ Note: In both scenarios, these are just what I perceive to be the big reasons why it was "thank you, next". There were other reasons and life is not an exact science where I can say it was 43% this reason, 12% that reason, etc.