I have been out of school and working for 4 years, the last 2 as UX Engineer at a small VC-funded Canadian internet startup (Company A). It's a delightful place to work, conveniently close to where I live, with a good salary and a great CEO who understands and appreciates the design process and generously provides any resources I need.
At the same time, I have been freelancing on the side on non-competing projects (aside: we had a mutual understanding with Company A about this). One of those freelance gigs has been ongoing UX design for an even smaller US startup (Company B). This has been mostly a labour of love. I loved the idea behind it, and also knew the founder, so I did all the work for them remotely and at a discounted rate (in exchange for options in the co.).
At this point in time, both of the products [which I did the design for] have been built and deployed. While they both enjoy good adoption rates, Company B's product has been by all accounts the more successful of the two, and they have just raised additional funding. By contrast, there has been a more subdued atmosphere around the office at company A for the past 2 months, and a lack of clear direction about what we should work on next, now that the original product isn't performing as we expected. There has been endless talks with major companies going on for months, about possible collaborations or selling the product to them, but seemingly to no avail. There has also been a lot of talks about potential products we can build next, but we haven't committed to any of them yet.
Company B, just having received additional funding, made me an offer to become full-time. The new position would be Director, UX, with stock options and a 30% increase in salary. I initially rejected the offer because I was not ready to move to the US, but they still wanted me, and they agreed to me working remotely from my home in Canada. (aside: I only get the benefits if I decide to move there).
It seemed like a logical decision to move; I had freelanced for them for 1.5 years and enjoyed working with the CEO. I let Company A of my decision last week (and told Company B I have accepted their offer).
Now, Company A has come back to me with another offer: promotion to Director, UX with additional stock options, a slightly higher salary than what Company B is offering me. Plus some other perks and I get to keep my health benefits. The CEO shared my concern for the lack of direction and promised that there will be a change of direction, with an amazing new idea that we are going to be working on (no specifics). He also reminded me of the options I have already vested, and how much I would lose if the product we have built would get acquired.
As you can see, I am faced with a big dilemma:
Should I switch and start [almost] fresh with Company B, working remotely from home, but on a product that I enjoy working on that has enjoyed modest success?
Or Should I continue with the company I have been with for 2 years, accept the slightly-better financial offer, and the promise of exciting things we are going to be working on?
I am having an extremely hard time deciding. I was hoping some of the board members who have switched more careers than me could share their insights. Hopefully this can help other designers who are in a similar situation as well.