Cyril Boisard‘s career is a testament to the power of curiosity and adaptability. His journey began in the realm of electronic engineering and R&D, but a thirst for deeper knowledge led him to pursue a master’s degree in computer science. Boisard’s early career saw him thrive as a software engineer across diverse landscapes, from multinational corporations to nimble web agencies, spanning both North America and France. He honed his skills in consulting and agile coaching, developing a knack for understanding complex systems and fostering collaboration.
Seven years ago, Boisard’s path took an unexpected, yet transformative, turn. He joined Workleap, initially focusing on talent management and coaching, before ascending to his current role as People Director. This unique blend of technical prowess and people-centric leadership has proven invaluable in navigating the challenges of remote work and digital transformation—a landscape Workleap has mastered under his guidance. During his tenure, Workleap has expanded its portfolio to five products through strategic acquisitions, doubled its workforce, and successfully transitioned to a fully remote operating model.
The Turning Point: From Tech to HR
The catalyst for this shift? Boisard credits his experience mentoring and coaching technical teams, which naturally drew him toward the human side of leadership. However, it was a meeting with Workleap’s Chief People Officer that solidified his decision. “Through our conversations and her vision,” Boisard explains, “I saw how HR could be a strategic force in driving team performance, culture, and organizational growth.” He recognized that the skills he had cultivated in engineering—complex problem-solving, cross-functional collaboration, and data-driven decision-making—were highly transferable to the world of HR.
Leveraging Engineering in People Leadership
“I decided to take the leap into HR and have never looked back,” Boisard reflects. His technical background, far from being a detour, has become a significant asset, providing him with a deep understanding of systems and processes. Today, as Director of People at Workleap, Boisard leverages both his engineering expertise and his passion for people to cultivate high-performing teams across North America, proving that sometimes, the most innovative leaders come from the most unexpected backgrounds.
In our latest Faces, meet Cyril Boisard.
Who is/was your biggest influence in the industry?
Throughout my career, I’ve had the chance to work with many amazing leaders who’ve influenced how I approach people leadership, but one person really stands out — Kahina Ouerdane, the Chief People Officer at Workleap. Kahina has an incredible ability to bring people together, create a truly collaborative environment, and guide teams through all kinds of transitions — whether it’s scaling quickly or managing complex M&A projects. What really struck me was how she balanced deep empathy with a strong strategic vision. That combination made a lasting impact on me and continues to shape how I lead today. She also took a chance on me when I transitioned from a software role to HR, which I’m incredibly grateful for.
Another key influence was the person who gave me my first job. He taught me the importance of a strong work ethic, resilience, being reliable, and always following through on your promises. He also led by example, and those values are still at the core of my own leadership style. To me, it’s all about leading with integrity and being someone your team can trust.
What’s your best mistake and what did you learn from it?
My perspective on mistakes is shaped by my background in software and electronic engineering where iterations and trial and error are key. I don’t view mistakes as failures; rather, I see them as valuable learning experiences. Every challenge is an opportunity to improve, innovate, and push the boundaries of what’s possible.
For example, early on in my career, I took on a leadership role in a project that had some technical and team communication challenges. Initially, I thought I had all the answers, but the reality was much more complex. Rather than seeing it as a failure, I used it as an opportunity to reassess how we approached problem-solving, communication, and collaboration. I learned that leadership isn’t about having all the answers but about creating an environment where everyone can contribute, take risks, and grow from experience.
In HR, this philosophy translates well. I believe in fostering a culture where challenges are seen as opportunities to drive change, challenge the status quo, and find simpler solutions. If I had to name a ‘best mistake,’ it would be this experience because it reshaped my approach to leadership and team development, reinforcing that mistakes are just stepping stones to progress.
What’s your favorite part about working in the industry? What’s your least favorite part, and how would you change it?
What energizes me about this field is seeing organizations transform through smart integration of technology and people practices. Coming from both software engineering and HR, I get excited about building bridges between these two worlds, and Workleap recently moved IT support to report under HR, opening up new possibilities for improving how people experience work. I love seeing how our products work together to create insights we couldn’t previously see, like connecting engagement data with organizational structures to understand what’s happening in different parts of the company.
The frustrating part of our industry is watching companies resist necessary changes, from giving remote work the attention it needs to investing in technology that streamlines and drives meaningful employee experiences. Too many organizations are falling back on return-to-office mandates because they’re unwilling to develop new capabilities and adopt innovative tech that could make HR a more connected, informed and powerful part of every organization. When HR isn’t tech-savvy enough, a ripple effect occurs: HR teams can’t effectively evaluate tools, struggle to create good digital experiences for employees and end up defaulting to old solutions that don’t work in today’s environment. As someone who’s spent time on both the technical and HR sides, I see how this gap holds back real progress in making work better for people.
I also find it frustrating that measuring performance and maintaining connections in remote environments is still such a challenge for many organizations. Some companies just want to recreate office practices in a virtual setting instead of developing new approaches that fit how people actually work today. We need to fundamentally rethink how we approach these challenges, rather than attempting to digitize old ways of working.
It sounds like through your experience you really care about people, and you want to help them feel safe and comfortable, which is important in the industry. Please elaborate here.
Here’s the thing about working with people — you need to understand what they’re experiencing daily to improve those experiences. In our company, we’re remote and hybrid, and one of our biggest challenges is creating meaningful connections. It’s not just about whether someone’s engaged, it’s about whether they feel connected to the organization and their colleagues and able to collaborate.
We’ve developed a flexible work policy that gives people autonomy in scheduling and location while maintaining core collaboration hours for effective teamwork. Our flexible vacation policy demonstrates our trust in our people and aim to reduce stress around time-off management.
One aspect of this that I’ve been thinking about lately is understanding people beyond their generational labels. Instead of focusing on whether someone is Gen X, millennial, Gen Z, etc., we need to understand where people are in their life journey. What current challenges or major life milestones are they facing? What do they need right now to be at their best? Two people of different ages might be going through similar life experiences and need similar support. By creating HR policies that respond to personal milestones and challenges, we can develop a more performing workplace that genuinely addresses the diverse circumstances of our workforce and the needs of the business.
How can HR most effectively demonstrate its value to the leadership team?
HR departments today need to show their value through real, measurable impact. Our research with The Starr Conspiracy revealed something significant: Organizations that invest more in employee experience see 1.5 times better outcomes in areas like manager feedback and workplace fulfillment. That’s the kind of concrete data that demonstrates HR’s strategic value.
The next frontier is the partnership between HR and IT. We’ve recently moved IT support under HR at Workleap. Instead of IT fixing tickets and HR doing HR tasks, we’re working together to improve how people experience work.
Tech is such a significant component of how we work — laptops, project management software, email and instant communication tools that keep us updated and help us collaborate, problem-solve and accomplish our goals. IT is the backbone of the employee experience. However, most HR teams aren’t tech-savvy enough for today’s digital world, and this disconnect inhibits employees’ everyday work — their experiences with their teams, managers and the organization as a whole. IT isn’t under HR’s jurisdiction at most organizations, but it should be because of the detriment these tech gaps can have on the employee experience. Too many companies fail to connect the dots between IT and HR, leaving teams with disjointed tools, processes and potential frustrations.
Where do you see the industry heading in five years? Or are you seeing any current trends?
Here are a few ways I see our industry shifting in the coming years:
The IT-HR Connection
I’m seeing a fascinating shift in how companies think about technology and people operations. Traditionally, IT has always been viewed as a cost center — it reports to the CFO because of the need to manage a big budget for laptops, software licenses and other equipment. But this mindset really needs to change. Technology isn’t just about managing costs anymore. It’s fundamental to how people experience their work, especially in remote and hybrid environments.
As I mentioned earlier, at Workleap, we’ve recently moved IT under HR. It’s still new, and we’re figuring things out. But this decision makes sense because of my background in both worlds. Most HR leaders at smaller companies, let’s say under 500 people, might have teams of three to five people focused on things like pay and performance. But they often struggle with the technology piece. When IT and HR work separately, you end up with solutions that might work technically but don’t really serve people well.
AI and Personalized Development
Something really exciting is happening with AI in employee development. Think about how we’ve traditionally done training with everyone receiving the same program, regardless of their role, experience or career goals. That’s changing dramatically. AI is making it possible to understand exactly what each person needs to grow in their career and deliver that learning right when they need it.
Moving from Looking Back to Looking Forward
Many organizations today spend too much time analyzing what already happened instead of preparing for what’s next. We’re focused on building predictive analytics capabilities that help identify potential issues before they become problems. With AI and better data integration, we can start seeing patterns that weren’t visible before. Where are we likely to see retention problems? What skills will we need in six months? How might organizational changes impact employee satisfaction?
Remote Work Evolution
Remote work is here to stay, but we need to get much smarter about how we do it. Successful remote work requires a complete rethinking of how we collaborate. It’s not just about having Zoom calls all day. We need to get better at asynchronous communication, using technology to create meaningful connections and measuring productivity in ways that make sense for remote work. The companies getting this right are the ones investing in both the technology infrastructure and the cultural changes needed to support remote teams.
What are you most proud of?
I’m really proud of how I’ve managed to blend my technical mindset with a people-focused approach to drive real change. In my past roles, I was always solving problems on the technical side, but in HR, I’ve shifted that focus to empowering people to tackle challenges on a much larger scale. It’s about creating a more engaged and efficient workforce. I’ve taken the same problem-solving mindset I had in software development and applied it to talent management, employee development, and shaping organizational culture. It’s been a game-changer, allowing me to bring fresh perspectives and innovate how we do HR.
One achievement I am proud of is guiding the IT support team through the transition into HR. It wasn’t just about changing departments — it was about rethinking how IT can play a critical role in supporting people and culture. We focused on aligning technology with employee needs, engagement, and growth, which made a huge difference in both the tech side and the overall employee experience. The result? Smoother workflows, stronger team dynamics, and a much more integrated approach to supporting the entire organization.
I’m also proud of leading M&A integrations. Merging teams and cultures can be incredibly challenging, but I focused on building trust, creating clear communication channels, and ensuring that everyone felt supported during the transition. It was rewarding to see how those efforts helped us bring together diverse teams and build a unified culture, all while maintaining a focus on long-term growth and success.
Do you have any advice for people entering the profession?
Technology isn’t optional in HR, especially with remote and hybrid work. You must understand how digital tools shape how people connect and collaborate. If your workforce is distributed across different locations and time zones, figure out how to create meaningful connections through technology. It’s about making the digital workplace feel as natural as being in the office together.
Embrace predictive analytics for HR. Many HR departments are sitting on a goldmine of data and need to realize its full potential. Predictive analytics can transform this data into actionable insights, helping forecast turnover risks, identify high-potential employees and predict future skill gaps. By adopting a data-driven approach, HR can shift from reactive to proactive, strategically aligning people management with business objectives.
Get serious about onboarding: It’s your chance to set the tone for someone’s entire experience with your company. That first impression shapes people’s feelings about their role, team and organization. With remote work, you can’t rely on those casual office interactions to help people feel connected. Be more intentional and structured about creating those connections from Day 1.
Make HR processes as easy for employees as using their favorite apps. People shouldn’t have to jump through hoops to get basic HR information or manage their benefits. Give them good self-service tools, make things accessible, and make it simple. When employees can handle routine issues independently, HR can focus on more strategic work.
Don’t get so caught up in technology that you forget what HR is really about: people. Data and analytics are important, but they’re tools to help us better understand and support our people, not replace human connection. You still need those one-on-one conversations and check-ins where you listen to what people are saying. Technology should enhance those human relationships, not replace them.
Anything else you’d like to add? We can talk about anything you’d like to discuss here.
One thing I’d like to add is how much I value collaboration and the ability to navigate complexity. As organizations grow and evolve, the challenges become more multifaceted — whether it’s managing cross-functional teams, leading through M&A, or integrating new technologies into business processes. I’ve learned that the ability to collaborate across different functions and adapt to complexity is essential for driving success.
My journey from tech to HR leadership has really highlighted the importance of breaking down silos and fostering open communication. We don’t always have all the answers, but by bringing people together — whether it’s IT, HR, or leadership — we can tackle even the most complex challenges more effectively. It’s about aligning the bigger picture and building solutions that work for everyone.
I’m passionate about finding the roundabout solution to any problem, as Aaron Dignam explains in his book Brave New Work, challenging the status quo, experimenting and making the whole greater than the sum of its parts.