5 minutes with Orly Lynn, Head of Global Inclusion and Diversity at Contentsquare


Katie Leask

September 13, 2021 | 5 min read

This month, we’re delighted to welcome Orly Lynn to the CSquad. Orly joins as Contentsquare’s Head of Global Inclusion and Diversity, bringing with her a ton of expertise and ideas to drive positive change within the industry and beyond.

Over a cup of coffee on a sunny Wednesday afternoon, we chatted to Orly about her career and biggest passions, plus her advice on launching your own DE&I agenda. Here’s what she had to say.

Tell us a little bit about you, your career, and your passions…

My career journey has been such a wonderful and fruitful one. I first came to diversity, equity, and inclusion at an introspective time in my career when I wanted to change how organizations thought about underrepresented minority groups across the globe.

When I first started out in financial services, I was part of these little grassroots groups called ERGs. These were super important because they taught me the importance of having a voice in an organization, of knowing and championing what was important to me as an employee. But they also taught me that employers really listened to the needs of their employees through employee resource groups, and that’s how I began to understand the power of the collective voice.

Though quite a few years ago now, that was the moment I decided that DE&I wasn’t going to be just a job for me. It was an entire movement; one that was changing and taking on a different life – one that was becoming very relevant in the workplace and beyond. It went beyond simply ‘doing the right thing’ and it was something I wanted to be involved with. So I decided to make an intentional pivot in my career to become a diversity, equity, and inclusion practitioner.

What is your most memorable career experience so far?

When I realized that I wasn’t working in a way that honored people or the work I do. So I decided to take a leap of faith and walk away from a safe role to start my own business. 

As a woman, as a professional, and as a person of color; that was the moment I looked inwards and said: “This is how I’m going to move forward and these are the things I will no longer stand for. This is what diversity, equity, and inclusion means to me and I’m going to do it on my own terms.”

That was the scariest moment in my career, but also the most memorable. I don’t think there’s ever a right moment to do something scary, so I remind myself to do something scary as often as I can because you don’t ever want to look back and say, could have, should have would have. 

And who better to help organizations understand and develop strategies and initiatives than someone who passionately believes in the work they do and who is also considered an underrepresented minority? That’s me!


Why is DE&I so important, and why now?

For me, it’s because we have to change what has historically been thought of as DE&I to what it truly means. Oftentimes when people hear the words diversity, equity and inclusion, most people will think, “oh gosh, this is about gender and ethnicity or race” – but it’s so much more than that.  

While the areas where we tend to find deeper-rooted challenges may come from gender, ethnic, and racial topics, true success is understanding there’s actually a spectrum. 

And in that spectrum, we’ve got people sitting on either end – true diversity and inclusion is understanding and respecting all the various points within the spectrum. 


So what brings you now to Contentsquare?

Because I felt there was something here that would spark the strategist and practitioner in me, like the very first time I decided I wanted to be a DE&I practitioner. 

Previously, I’d been leading DE&I for a global bank and felt I’d made it to where I wanted to be. But then I realized that the larger and more bureaucratic an organization is, the more complicated the work that I do would be. Not that I’m not up for a challenge, but I no longer wanted to be part of a DE&I agenda that simply ‘checked a box’. I wanted more than that! 

I wanted to join a company that was ready to stand up and say “We’re not doing this because it’s the right thing to do. We’re doing this because we want to create a space where we can innovate – and we want the top people innovating with us. It doesn’t matter what race, ethnicity, gender, visible or invisible differences, because we believe in something more than that.” 

Contentsquare showed me right away they were serious. They had the kind of startup mentality that would allow my work to become intrinsically woven into everything they do. The fact we’re growing at such a fast pace means we can bring diversity, equity, and inclusion along on the journey and let the world know who we are and what we believe in – not just from a business perspective but also from a people perspective.


What key initiatives are you looking to launch at Contentsquare?

I want to be thoughtful about our approach and initiatives, so I’m taking my time to design a strategy, with the help of our employees, that’s unique to Contentsquare. We have tonnes of really fun things coming, so stay tuned!

One thing I will say, though, is that I’ll be working on a global DE&I message that resonates in every geography. If we want to truly create an inclusive workforce, we have to take into account all of the people and different geographies in our organization and those we touch as a business, too. 


In your opinion, what companies are paving the way in terms of DE&I?

Outside of the big names like Google and Facebook, there are many smaller companies out there who are doing some amazing work – and I really believe in the power of the underdog! 

When organizations begin to understand and pinpoint the areas where they’re lacking, they often have a much better approach to defining their DE&I agenda and how they’ll evolve over time. And, importantly, it’s a journey the organization goes on together. 

I think the larger your organization is and the later on in the journey you start talking about DE&I, the harder it becomes. Although Contentsquare is by no means an underdog, I believe we’ve got the right mentality. We’re bringing DE&I along with us on this journey as we grow and we’re committed to becoming an inclusive workplace that truly honors diversity strands – not just in one geography, but in all of them.


What is your best advice for someone looking to promote DE&I within their own business?

Listen to your employees! They’re the people running your business and giving their heart to your organization. They’ll give you their true and unfettered opinion of what they’d like to see happen, plus what diversity, equity, and inclusion means to them. Then you can collectively begin to decide what DE&I looks like for your organization.