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UpKeep Maintenance Management

Engaged employer

UpKeep Maintenance Management Reviews

3.9

76% would recommend to a friend

(69 total reviews)

Ryan Chan

78% approve of CEO

64% positive business outlook

UpKeep Maintenance Management has an employee rating of 3.9 out of 5 stars, based on 69 company reviews on Glassdoor which indicates that most employees have a good working experience there. The UpKeep Maintenance Management employee rating is in line with the average (within 1 standard deviation) for employers within the Information Technology industry (3.9 stars).

Reviews by job title

69 reviews
4.0
11 May 2026
Recommend
CEO approval
Business outlook

Pros

Growing company, opportunity to experiment with AI

Cons

Departments vary in maturity level and can make cross dept collaboration challenging at times

avatar
UpKeep Maintenance Management Response
2d
Thank you for your feedback and for being part of UpKeep for more than three years. We're glad to hear you've found opportunities to experiment with AI and contribute to a growing company. We also appreciate your perspective on cross-functional collaboration. As we continue to scale, we're focused on improving alignment, processes, and communication across teams to create a better experience for everyone. Thank you for your contributions and continued support.
2.0
8 Feb 2026

Started OK, then became miserable. Culture of fear.

Anonymous employee
Recommend
CEO approval
Business outlook

Pros

- Some great coworkers. The team is full of smart individuals doing their best despite the environment. - Effort by the People Team to build good culture. - Founder is passionate about his company. - Founder has an early adopter mindset. - Opportunity to experiment with AI. - Your experience may not be so bad if you do not have to interact with the founder, but that applies to fewer people than you would think because he is controlling and a micromanager. He constantly meddles in various departments at all levels.

Cons

- Unfortunately, the People Team's efforts to build good culture are undermined by the Founder/CEO. - At least 20 people have said he is difficult to work with, or a synonym, and that is just those who have outright said so directly to me or in a conversation I was a part of. Not everyone will say it out loud, and there are many people in the company I do not interact with regularly. 20 is a majority of the ones I do. - For someone who considers himself a big thinker, he is close-minded, out of touch, and intolerant. Whatever he says goes, even if it does not make sense. He does not even feel comfortable with you expressing disagreement. He calls it "resisting." He wants yes men, exploits the power dynamic to create that environment, and then he will turn around and ask "why is no one thinking for themselves?" - Sometimes it feels like you are talking to a child who could fire you if you do not comply. - I have seen him pull power moves, like stress tests and loyalty tests, across departments. He is disrespectful to people. He also disregards instead of trusts their expertise. He struggles with empathy and people skills, despite being an extrovert. - He either does not know how to be a good leader or takes pride in being a tyrant, and I am not sure which is worse. - The pay is below market and leadership keeps telling everyone we have so much cash and are keeping levels high as though we care if it is clearly not being invested in us. Stingy and tone-deaf. - Little career growth. People constantly disappear (fired) or leave for huge pay bumps at other companies. - Several people I know are actively looking for new roles. I am writing this for the jobseekers, not for any hope that he will change. You will see some themes echoed across other reviews, and he reads and responds to them. This is a company full of good people, but many have tried to make progress here and quietly moved on after realizing the core issue is not changing. Who do you report the CEO to? He thinks his way is getting him results, but look at how this company lost its first-mover advantage. Look at how he is trying to recover it by shoving his new strategy down customers' throats. Look at the turnover. People brave enough to disagree with him leave, get threatened, or get fired. The founder has asked why people are not thinking for themselves without recognizing how little room he leaves for that thinking to matter. I wonder if he just thinks they were all holding him back as opposed to going through the perhaps uncomfortable exercise of introspection. Or maybe he outsourced that critical thinking to ChatGPT, too.

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UpKeep Maintenance Management Response
2d
Thank you for taking the time to share your feedback and for recognizing the dedication of your colleagues and our People Team. We understand that employees can have different experiences, and we're sorry to hear yours was not a positive one. We take feedback seriously and continuously work to improve how we communicate, develop our people, and support a strong culture as we grow. We appreciate your contributions and wish you the best in your future endeavors.
4.0
12 Mar 2025
Recommend
CEO approval
Business outlook

Pros

Manager is wonderful and does everything to support his SDR's

Cons

Base pay is low Company leadership makes strange decisions

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UpKeep Maintenance Management Response
1y
Thank you for sharing your experience as an SDR at UpKeep. We're glad to hear your manager was a strong support and made a positive impact during your time with us. We also appreciate your honest feedback regarding compensation and leadership decisions — these are areas we take seriously, and we continue to evaluate both to ensure we're aligning with our team’s needs and company goals. Wishing you all the best in your next chapter, and thank you again for being part of the UpKeep team.
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Glassdoor has 75 UpKeep Maintenance Management reviews submitted anonymously by UpKeep Maintenance Management employees. Read employee reviews and ratings on Glassdoor to decide if UpKeep Maintenance Management is right for you.