When Mandy Mekhail joined ClickUp in November 2020, the company had fewer than 100 functional employees and exactly two open roles: customer support and marketing. She had no formal background in customer support. She’d spent her career in education. But she applied anyway, got the job, and over the next five years built and led teams across customer support, solutions, enablement, and eventually the people function itself.
Today, ClickUp has around 1,200 employees spread across San Diego, San Francisco, Dublin, Sydney, and Manila. Mekhail serves as Chief of Staff of People. And the principles she’s used to scale the organization are worth paying close attention to, whether you work in tech or not.
Her story is a good reminder that the best people leaders don’t always come from traditional HR pipelines. What they do have, though, is a deep instinct for what actually motivates people and how to build systems that channel that motivation into results.
Hire for Passion, Not Pedigree
From day one, CEO Zeb Evans made a deliberate choice to skip the degree requirements and the conventional credential checklist. He’d found early success hiring from ClickUp’s own power user base, and what he noticed was that those people didn’t share a background or a credential but rather a belief in what the product could do. “He found success in hiring from the power users of ClickUp, which is a pretty untraditional path,” Mekhail told me. “Let’s just double down on that.”
That philosophy extends to how ClickUp sources candidates. The team actively recruits from ClickUp’s own user communities, online forums, and solopreneur networks. The logic is that someone who already believes in the product deeply enough to build their work life around it will bring that same energy to their role inside the company. It’s a counterintuitive recruiting strategy, but it’s held up through a period of rapid growth.
The practical implication for hiring teams is worth sitting with. When you strip away degree requirements and lean into skills, drive, and alignment with mission, you often end up with a more motivated and more diverse candidate pool. The question to ask isn’t “does this person have the right credentials?” but “does this person care, and can they do the work?”
Onboarding Is a System, Not an Orientation
Mekhail spent a stretch of her ClickUp tenure building out the support training function, and the results were striking: roughly 500 employees onboarded with a 99% success rate on role KPIs within 90 days. That doesn’t happen by accident, and it doesn’t happen by throwing a handbook at someone during their first week.
Her approach was to work backwards from the outcome. She started by defining what fully productive looked like at the six-week mark, then mapped every training element to that goal. The most common customer use cases shaped the curriculum. Areas with lower customer satisfaction scores got more attention. And critically, every piece of training happened inside ClickUp itself, so new employees were simultaneously learning the product as users while preparing to support it professionally.
“The number one step is making sure that they are embedded in it, they understand it fully, both as a user, but also as a customer themselves,” she explained. A customer support employee who only knows the product as a set of features to explain is going to give a very different experience than one who’s actually tried to build a workflow in it, hit the same frustrations a customer might hit, and figured out how to get around them. Product fluency, in Mekhail’s view, is the foundation everything else is built on.
From there, the training built in layers. New hires would start with the basics of a feature, then practice explaining it in a group hot seat format, then move to diagnosing what a customer actually needed rather than just answering the surface-level question. That last step is the important one. The goal was to produce employees who could anticipate what the customer needed two weeks from now and head off the next ticket before it arrived.
The peer-based structure was intentional too. Learning in a group, in a safe environment, with the freedom to get things wrong before going live, is how people actually build confidence. Mekhail drew directly on her background in education to design it that way, and the methodology translates remarkably well to corporate onboarding. Most organizations treat the first 90 days as an information transfer problem. ClickUp treated it as a confidence-building problem, and the outcomes reflect that difference.
Culture Doesn’t Scale by Accident
Managing culture across 1,200 people in multiple countries and time zones is genuinely hard. Mekhail doesn’t pretend otherwise. But her framework for how ClickUp approaches it is useful precisely because it’s concrete rather than aspirational.
The key, she says, is having a unifying factor strong enough to hold together whatever subcultures naturally develop in different offices and regions. For ClickUp, that’s the mission, the vision, and a set of 10 core values that the company actually recruits for, not just posts on a wall somewhere. Because those values were screened for at the hiring stage, employees across Manila, Dublin, and San Diego are operating from the same baseline assumptions about how to treat colleagues and customers, even when they’ve never met in person.
“No matter what’s going on, even if you’re eight hours in the future or eight hours in the past, you’re leading with the good intent that your colleague wants what’s best for you, wants what’s best for the customer,” she said. “You’re in it together to solve the problem.”
That shared intent doesn’t eliminate miscommunication across cultures and time zones, but it does mean that when friction arises, people can get to the real issue faster. They’re not spending energy wondering whether the other person is acting in good faith. That’s a significant advantage in a distributed organization, and it’s one that has to be built at the recruiting stage, not patched in later with team-building exercises.
The operational side of inclusion is equally concrete. All-hands meetings rotate across time zones so the same people aren’t always attending live and others aren’t always watching recordings. A hundred percent of company communication flows through ClickUp’s own platform, in English, so that institutional knowledge stays accessible to everyone regardless of when they joined or where they’re located. That last point matters more than it might seem: it means a new hire two months from now can search a conversation from two years ago. It also means the company’s AI tools are continuously trained on a rich body of real context.
The communication discipline extends to individual boundaries too. On her phone, Mekhail keeps the ClickUp mobile app turned off after 5pm through a phone-level setting, so checking work after hours requires an active decision. It’s a small thing, but it’s the kind of behavioral norm that, when modeled from the top, shapes how an entire team thinks about recovery time.
AI as a Multiplier, Not a Replacement
This is probably where ClickUp’s approach diverges most sharply from current thinking at most organizations.
Since the summer of 2025, every ClickUp employee has had a dedicated hour per week to play with the company’s AI agent tools, specifically a proprietary interface called Super Agents that lets users program virtual coworkers to handle tasks automatically. There’s no rubric, no performance expectation, no “good or bad” attached to what people build. It’s designed to be a genuine playground.
“Because we give them the time to really play with it, people naturally let go of a lot of that fear and see AI not as a threat, but as an opportunity to boost their own skills,” Mekhail said.
The results have been significant. ClickUp currently has around 5,000 AI agents deployed across 1,200 employees. People share their wins in a dedicated chat channel, formatted with the help of another agent that keeps the posts consistent so anyone can skim through and spot useful ideas quickly. At all-hands meetings, there’s a standing segment called the “help wanted board” where employees can post agent ideas they haven’t had time to build, and others can pick them up, build them, verify them with the requester, and share the finished product with the full company.
The architecture matters here too. ClickUp built its AI agents to have the same data permissions and organizational structure as human employees. An agent can appear on an org chart, report to a manager, and operate within the same information boundaries as any team member. The practical effect is that when a person leaves, their agent doesn’t leave with them. The knowledge persists in the workspace.
Mekhail is thoughtful about where AI falls short in HR contexts, though. She sees a gap between what’s currently happening (automating operational tasks) and what’s next: using AI to do genuine sentiment analysis on how people experience those processes, and using that analysis to inform how you automate further. “There’s a world in which you really need to retain a lot of human interface,” she said, “but it’s taking the inputs from AI and then doing something really special with it.”
On the broader question of AI-driven layoffs, her view is clear. “What I firmly believe is the correct thing to do is to really use AI as a multiplicative tool, not a replacement. It’s not taking out people for the sake of AI. Instead, it’s recognizing what AI unlocks so that your humans can do even more.”
Lessons Worth Carrying Forward
Mekhail’s experience at ClickUp is specific to a high-growth tech company, but the underlying principles travel well.
Hiring on passion and integrity rather than credentials opens doors to talent that traditional filters miss. Onboarding built around clear outcomes, product immersion, and peer learning produces confident employees faster. Cultural cohesion at scale requires a genuine shared mission, not just strong branding, and it requires operational habits that back that mission up. And AI integration works best when employees have real time and real freedom to explore it, rather than being handed a tool and told to use it.
The thread running through all of it is something Mekhail kept coming back to throughout our conversation: the importance of giving people both high expectations and the genuine support to meet them. “If you have high expectations, but they’re communicated clearly,” she said, “that person is much less likely to burn out because they understand what’s expected of them, but there’s enough respect in the relationship that they’re going to feel safe communicating when they need more support.”
For HR leaders outside the tech world wondering how any of this applies to them, Mekhail’s advice is simple: start with yourself. Whatever you feel about AI, about skills-based hiring, about distributed culture, shows up in the decisions you make and the hesitations you project. The leaders who do the work of genuinely understanding these shifts, well enough to explain both their promise and their limits, are the ones who earn the credibility to bring the rest of the organization along with them.
Brandon Laws is a workplace culture and leadership enthusiast, host of the Transform Your Workplace podcast, and VP of Marketing and Product at Xenium HR.