Advice: "I joined a promising startup expecting an IPO, but the job is miserable. What should I do?"

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Dear Quota Team,

I work for a tech startup as an AE. The company has been around for about four years or so. In 2021, the company raised a huge amount of funding to speed up growth. I don’t want to say how much or give any other details about the company because people might be able to figure out which company it is, and I’d like to keep this confidential. But the money raised was over nine figures. 

The company raised this money despite having revenue under three million dollars a year. The huge round of funding was one of the main reasons why I took this job. I was under the impression that if a company raises that much money, it means they’re extremely successful or about to be extremely successful. After all, why would smart investors put in over a hundred million dollars into a company that hasn’t proven itself, right?

Well, unfortunately, I am finding out the hard way. I’ve been here for over a year and a half, and in that time, the company has really struggled to close new business. The lead flow is pretty good because the company has a bunch of money to spend on marketing. But our sales cycle is insanely long, and we’re not closing anywhere near the number of deals we should be. Basically, the customers tend to say that our product is a “nice to have” not a “need to have.” 

I was very excited to get this job, because of the idea of joining a rocket ship that was going to eventually IPO and make me a millionaire. Seriously, I was convinced this was the opportunity of a lifetime. But in reality, it’s kind of a miserable place to work. I feel like management kind of knows the company is not going to ever become a unicorn and they’re not as excited about anything as they were when I first came on right after all the funding hype. If you were in my shoes, would you move on to a different company or stick it out here and hope things get better? I guess I’m mostly venting because I can’t have this conversation with anybody at work. Thanks! 


Dejected in Location withheld 


Dear Dejected,

This is a perfect example of things not always being what they appear to be. A job you expected to be amazing ended up being a bit of a dud. It happens, and definitely not just in tech. Sales reps are known for moving on to greener pastures, and quite often, the leads or the culture, or the pay, isn’t what it was cracked up to be. 

As far as whether you should stay or go, you might want to reread what you wrote. “It’s kind of a miserable place to work.” We spend forty hours or more at our jobs every week, and if many of those hours are miserable, it’s really not the best use of our time on this earth. 

There are plenty of great tech sales jobs out there. You might want to consider going to a later-stage company, or even an established player. Make sure to do your research beforehand. Check out RepVue and other transparency platforms before accepting an offer. And don’t worry, if you stick in sales long enough and commit yourself, you can definitely become a millionaire. It’s just usually not as quick or easy as it might seem. Good luck!   

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