The hiring process at Windsor.ai takes an average of 14 days when considering 1 user submitted interviews across all job titles. Candidates applying for Account Manager had the quickest hiring process (on average 14 days), whereas Account Manager roles had the slowest hiring process (on average 14 days).
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I applied through other source. I interviewed at Windsor.ai in May 2026
Interview
I had an interview with CEO. While the role itself was interesting, the interview experience was disappointing. A significant portion of the discussion focused on concerns about contractor fraud, abuse, and trust issues rather than my experience, accomplishments, or plans for the role. The CEO frequently interrupted answers, appeared dismissive of alternative viewpoints, and created an adversarial atmosphere rather than a professional discussion. Instead of feeling evaluated on my qualifications, I left the process feeling distrusted and questioned. Overall, the experience felt unnecessarily confrontational and did not reflect the level of professionalism I would expect from a leadership interview.
Interview questions [1]
Question 1
Upwork is full of scammers. Did you experience that in your previous company, and what did you do about it?
Fairly straight to the point. I had a screening, Demo Test, CEO interview.
The screening with the COO is okay, getting to know more about you and your background and he also seemed nice.
The demo didn't go well as expected, the instructions were very generic and knowing that you might not have a background with their product makes it more difficult.
CEO interview is not good. I didn't want to push for the final interview as I saw a few redflags already with the demo test they've prepared but still went in so that I won't regret it afterwards. But it turns out my gut feeling was right.
Their CEO is not as friendly as you might think, he seemed to be difficult to work with and egoistic.
Glad it didn't go well. Looks like it's not a good company for me.
I applied through a recruiter. I interviewed at Windsor.ai
Interview
5 minutes interview with technical HR, friendly person. They are asking questions based on linux, git and python knowledge. Interviewer is taking notes with tl:dv, quick response before the interview.
Interview questions [1]
Question 1
What's the difference between git fetch and git pull,
How to log most cpu based via linux terminal( ps aux)
Pythonic code type question, tricky part is {"1"} is set, not a dict, and ("1") is not a tuple, its still only a string.