Dropbox

Really strong engineering team. Teammates are curious and competent. I enjoy knowing that any random person I meet on a cross-functional project will generally be a pleasure to work with.

Plenty of big challenges to sink your teeth into. If you're up for the task, career growth has a stellar trajectory.

Work-life balance is excellent both on a weekly basis and regarding vacation. Unlimited vacation lives up to its claims here.

Managers frequently come from engineering, which leads to uneven quality. This is both a cause and symptom of high churn at the lower levels of management—bad if you subscribe to the idea that people work for good managers, not jobs. Let's just say that you should really like the job.

Lots of competitors in the space. Unfortunately, the heavy hitters are closer to existential threats rather than healthy rivals.

While the core systems are robust, duplicated efforts, wildly changing technical strategy, and poor knowledge-sharing abound. The same kind of self-defeating chaos that politics would generate at a larger company arises here naturally due to... dare I reuse that startup cliché... growing pains.

Poor retirement matching.

Control the quality of lower management more carefully.

Outline a stronger technical and product strategy with a time horizon of greater than a year. While it's nice that so many of our recent innovations have come out of random engineers hacking around, it does diminish confidence in leadership's ability to, you know, lead.

The recent rebranding, which appears to have been driven from the top down, makes my eyes bleed.

The core business has been and is doing well, so good job so far.