I applied through an employee referral. The process took 3 weeks. I interviewed at Middesk (San Francisco, CA) in Aug 2022
Interview
Pretty seamless experience; nothing super special.
Great chat with the VP of Engineering to start off the process.
1st technical screen was really enjoyable, very kind and personable interviewer which was refreshing given how engineering interviews typically go. Wasn't a crazy algorithm, instead an interesting technical problem that allowed me to showcase my thought process.
For the final, folks interviewing were relatively nice, but it seemed like the engineers were purposefully trying to create a more tense / high-pressure interview which I felt was unnecessary. I struggled with the system design portion because I couldn't define a certain type of object, and the hints given after I showed signs of struggle came off a bit abrasive and condescending.
Otherwise a good experience. CTO conversation was really down to earth.
Interview questions [1]
Question 1
No algorithms, more just fun technical challenges without any real gotchas as well as a pretty vague system design question about how to improve an existing process.
I applied through a recruiter. The process took 1 week. I interviewed at Middesk (San Francisco, CA) in Dec 2025
Interview
Interview Process:
Round 1: Recruiter screen
Round 2: Technical pair programming on CoderPad
Technical Round Details:
The coding assessment was straightforward and backend-focused, involving business verification logic with REST API/TypeORM results. The problem was practical and relevant to Middesk's work—primarily JSON parsing without algorithmic complexity.
Feedback:
I completed approximately 90% of the assessment but was rejected for "insufficient technical performance." When I asked the interviewer about completion expectations and performance criteria, she spent the remaining time discussing her personal experiences at the company rather than evaluating my problem-solving approach.
Concerns:
Having a junior engineer (10 months experience) conduct technical interviews for mid/senior positions raises questions about assessment consistency. The interview seemed to miss its stated purpose of evaluating thinking process and problem-solving skills. The mismatch between the straightforward nature of the problem and the rejection reasoning was puzzling.
Ad hoc interview process. Flakey recruiting process. Weak seeming ICs misread printed out test results during coding interview / didn’t know about blob storage during system design interview. Does not seem like a promising company.
Interview questions [1]
Question 1
Implement some API endpoints that parse input data and save to a database
I applied online. The process took 4 weeks. I interviewed at Middesk in Nov 2025
Interview
1. Recruiter call - nice
2. Easy technical screening - nice
3. Four-hour panel interview:
HM Talk - questions were aggressive, got interrupted multiple times;
Web API / DB technical question - not focusing on coding, but you must know all steps from DB creation to endpoint development;
PM brainstorming - nice;
System Design - focus on collaboration - nice;
Result: rejected, refusing to give feedback.
Interview questions [1]
Question 1
What improvement were you supposed to make for a certain past project?
Software Engineer applicants have rated the interview process at Middesk with 2.9 out of 5 (where 5 is the highest level of difficulty) and assessed their interview experience as 38% positive. To compare, the company-average is 36.4% positive. This is according to Glassdoor user ratings.
Candidates applying for Software Engineer roles take an average of 19 days to get hired, when considering 8 user submitted interviews for this role. To compare, the hiring process at Middesk overall takes an average of 21 days.
Common stages of the interview process at Middesk as a Software Engineer according to 8 Glassdoor interviews include:
Phone interview: 33%
One on one interview: 33%
Skills test: 25%
Group panel interview: 8%
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