ClickUp Customer Success Manager Interview Questions
& Process

I was really excited about this job because it matched my resume, especially my experience driving adoption. I thought I was there to contribute strategically, but it turned out to be a scam. I ended up doing over 50 hours of free work, thinking it was part of the hiring process. The role had been open for ages, and the process was super fast: one chat, a culture call, then a big assignment they gave me five days for. I worked myself sick trying to do an amazing job, all while juggling my full-time work, family, and missing my son's birthday. I basically delivered a full client strategy engagement for free, including a custom ClickUp workspace, onboarding frameworks, KPIs, stakeholder maps, gamified training, usage tracking, dashboards, a live walkthrough, and a presentation deck. The panel seemed impressed, with one admitting adoption was tough and another learning a new ClickUp feature. One panelist was super positive and said I'd hear back soon, but another was disengaged and rude, even walking out mid-presentation. This mixed reaction was weird, maybe deliberate. I told the recruiter about the positive feedback, and she said I was teaching them things and would update me. But then radio silence all week. On Friday afternoon, I reached out and got a rejection email almost instantly. When I called them out for essentially using me for free strategic work, the recruiter ghosted me. This kind of thing is happening a lot; companies are using 'evaluation' as a cover to get free labor. The whole process felt real, but it was just about extracting value, not finding the right candidate. Others have had similar experiences, being asked to 'help strategize' and then getting ghosted. ClickUp is exploiting candidates for unpaid labor instead of hiring people for strategy. If they learned from my demo, they got free consulting. Pay for insight and strategy. People are watching. Candidates, if a process moves too fast, the assignment is unpaid and strategic, or they seem more interested in your ideas than you, trust your gut. You're not being hired; you're being harvested.

The interview process had five rounds. The first two were with recruiters, then the hiring manager, followed by a peer who gave a presentation. The presentation prompt was very generic, which they admitted during the presentation. The last round was with the skip level. They didn't provide a demo license, suggesting a paid subscription might help with technical features for standing out. They mentioned needing someone to coach and mentor because the team lacked sales capabilities. Ultimately, they hired an internal candidate from the Philippines for a US-advertised role, who was chosen for presenting prior solutions for ClickUp clients. It felt like my time was wasted since it seemed like a formality.

The interview process was pretty standard, with four main steps. It started with a recruiter screen, then a hiring manager interview from team B, followed by a hiring manager interview from team A. The last step was a panel interview with the VP and a team member. This final panel interview also served as a technical assessment. They gave me a prompt a few days before, and then I did a mock client session with the panel to show what a typical day in the role would be like. The whole thing from start to finish took about 4 weeks, but ClickUp was good about giving updates a few days after each interview so I didn't have to wait too long to hear back.