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As a global company, if there’s one thing we’ve learned over the past few years, it’s this: culture isn’t confined to four walls. It’s built in the everyday moments; how we set goals, how we listen, and how we show up for each other, whether we’re down the hall or a time zone away. Our hybrid work philosophy is simple: optimize for outcomes and belonging, then give people the flexibility to do their best work.
That’s why we’re thrilled to announce that we recently were awarded the 2025 Chicago Top Workplaces award by Chicago Tribune and recognized for our approach to work. This award highlights Flexera’s dedication to building an outstanding workplace culture that values finding top talent and giving them a place to thrive.
At Flexera, we “Keep Score.” Not to micromanage, but to measure what matters. Coming out of the pandemic, we studied productivity and found that people working from home were just as effective, if not more. That data validated what many of us were feeling: flexibility fuels focus.
Our approach
We operate with two primary employee profiles. Of our nearly 2,000 employees worldwide, currently the majority are considered “Cloudie” (fully remote) and less than half are office-tied (hybrid). For people based near an office, we encourage them to come in for Together Tuesdays; one day a week designed for collaboration and connection. The rest of the week, employees are encouraged to work wherever they do their best work and managers are empowered to make the right calls for their teams based on goals, roles and individual circumstances.
This rhythm reflects how we work as a global company. Even on office days, your closest collaborator might be on a different continent. So, we invest in habits that scale across distance: weekly O3s (one-on-ones) are a way of life here, rotating meeting times across time zones, asynchronous channels so people can contribute when they’re at their best, and design choices that keep remote colleagues fully included. A small but meaningful example: in our All Hands sessions, our CEO doesn’t sit at a big table in a large room at HQ. He joins the same way everyone else does, at his desk—so the experience feels equivalent, wherever you are.
Designing offices for “purpose, not presence”
We have offices around the world and part of our hybrid work strategy is honestly assessing space needs to ensure we are effectively using space and not requiring employees to come into an office to solve a real estate problem. Over the last several years, we’ve downsized and closed smaller sites where we didn’t feel office space was particularly useful.
We’ve also redesigned our spaces around the moments that benefit most from being together: team working sessions, social connection and larger events. Think collaboration zones, hot desks for flexibility and large meeting spaces so teams can come together and work comfortably. When people come in, it’s to do something they can’t do as well on video.
Rituals that build connection
Connection isn’t an accident, it’s a practice. And we’ve learned it has little to do with whether you’re in an office or working remotely. Here’s how we make culture real, wherever you are:
- Events and celebrations: Quarterly Days of Connection bring employees together virtually and locally, while monthly Cloudie gatherings celebrate milestones for our fully remote teammates.
- Engagement and belonging: Throughout the year, we offer hybrid programming, sponsored by Flexera and our Employee Resource Groups, to foster inclusion and community.
- Recognition: Our digital recognition platform makes it easy for colleagues and managers to spotlight everyday contributions across locations.
- Listening and feedback: From regular engagement “pulse” surveys, skip levels, listening sessions, All Hands Q&A and “Candor Corner” where employees can ask anonymous questions, we gather insights in real time so leaders can act quickly.
For managers, we double down on what matters in distributed environments: managing by outcomes, balancing flexibility with accountability, practicing meeting hygiene and giving and receiving feedback. These behaviors are reinforced through manager standups, clear leader expectations and ongoing training on leading distributed teams and cultures.
Proof it’s working
We care a lot about engagement because it’s a leading indicator of performance and retention. Our scores have been consistently strong, and we’re seeing voluntary attrition at or below benchmarks. Meanwhile, our business has continued to grow. We’ve completed two acquisitions in the last two years and earned industry recognition, including Gartner accolades and year over year “Great Place to Work” awards in all countries we survey. The Chicago Tribune’s 2025 Top Workplace award is yet another proof point of that hard work. As one of our values is “Keep Score,” this hybrid model doesn’t work if it’s not delivering results for our customers, and for our employees too.
A lot of companies are going in the other direction, asking for more days in the office. We’re not. We believe one intentional day beats three obligatory ones when the rest of the system is built for clarity, trust and delivery. This approach is right for us because it’s grounded in data, designed for a global team and aligned with how our customers need us to show up.
And our hybrid model—rooted in our “How we Roll” values—isn’t a compromise. It’s a choice to design work around people and performance. That’s how we build a workplace where everyone can do the best work of their careers, together.
Interested in joining the team? Check out our careers page and browse open roles.
