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Here's when I ignored my golden handcuffs and left my job

Here's when I ignored my golden handcuffs and left my job

It’s hard to know when to leave stock options behind

You might assume that once you have gotten your offer, started at your company, started to exercise and sell your options then most of your decisions are already done. Unfortunately, the hardest decision is left to be made: when to leave. 

Since most companies continue to grant stock options to their employees every year or two, at some point you will have to make the decision to leave the stock option gravy train and move on to new pastures. When you are making an extra 25% on top of your salary (or more) from stock, that can be an incredibly difficult decision to make. 

I thought I would take some time today to dive into this concept and discuss the way I think about this.

The decision to leave for me is the exact opposite of the process of evaluating a company to join, which I do by looking at these three criteria: 

  • Are they good people?

  • Are the customers in love with the product?

  • Is the company a good investment?

When I am thinking about leaving, I ask those questions in reverse. Maybe the people are less good than they used to be. Maybe the product is less transformational, and the customers are less excited about it. Or, maybe the company and your stock just simply isn’t as good of an investment as it used to be. It might have appreciated to the point where you don’t think there is much potential gain left in the shares. 

When any of those conditions change, it might be the right time for me to leave. Although I can’t tell you when the right time might be to leave your company, I can tell you about the time when I chose to leave my golden handcuffs at Tableau behind and move on to greener pastures.  

Are they good people?

By 2017 when I had been at Tableau for 8 years, a lot had changed since I started. Although I loved many of my co-workers, we had also hired some Microsoft middle-managers that had begun to change the nature of the organization by introducing more bureaucracy and inter-departmental competition. It really killed the vibe, and introduced a negative competitive element to every discussion. There were Jabber (old-timey Slack…) channels just for bitching about other people, and the primary motivation of the rank and file was to see how early we could leave and still keep our jobs. There were a lot of people who were keeping a nice cushy 10-4 schedule (with no negative repercussions). In fact, there were no negative repurcussions for anything - it seemed like it was impossible to get fired. Now, this isn’t always a bad state of affairs as some companies fire way too quickly and ignore the possibility of developing lower performers, but Tableau took it way too far. Awful people kept their jobs for no reason, and it hurt the great people.

Are the customers in love with the product?

At the same time, Power BI (a Microsoft product) had been aggressively chasing after Tableau and was beginning to eat its market share. Tableau was still better, but it was much harder to explain why it was better. Compounding that was the slower pace of development caused by years of technical debt.

Less new stuff to talk about and more competition makes the day to day job a lot less fun as a marketer. Simultaneously, the company was trying to switch to a new subscription based model which was confusing to customers. Add it all up and Tableau as a product just didn’t look as good as it did before.

Is it a good investment?

Although Tableau was still a good investment when I left, it also wasn’t a “10x” investment. My shares weren’t going to be worth 10 times what they were within any reasonable time frame. As you can see from the image of Tableau’s share price below, I had been through quite an emotional journey over the course of the previous 4 years, and with the stock price at a new low my existing stock options were worth far less than they were before. Of course, over time they would go back up - something I felt fairly confident of even at the time I left - but it could take years. I knew it was better to focus on finding a new opportunity with more shares and better prospects than continuing to pour time and effort into Tableau.

over time.png

Any one of those changes would be fine on their own, but all three changes together made it clear that it was time for me to leave. 

When should you leave your startup if you have golden handcuffs?

There’s no way for me to tell you exactly when you should leave, but hopefully you will have developed enough intuition to know when the time is right for you by applying the evaluation criteria in reverse. You also have the tools you need to find someplace new, which is just as important as knowing when the right time is to leave. The two decisions are closely linked.

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