The Remote Work Revolution: Melanie Oberman Of Contentsquare On Building Strong Cultures in a Digital World
An Interview With Chad Silverstein
Define a working culture: Establish clear working principles and responsibilities across teams and time zones. If you’re vague about expectations, misalignment will creep in fast.
The remote work revolution has transformed how we think about work, but it has also raised important questions about maintaining culture and connection in a virtual world. To explore this important topic, we are interviewing Melanie Oberman, Chief People Officer at Contentsquare.
Melanie Oberman is Chief People Officer at Contentsquare, where she leads global people strategy and talent development. She previously served as CPO at Heap, helping build a high-performance culture ahead of its acquisition by Contentsquare in 2023. Earlier in her career, she held senior roles at Jetblack, Greenhouse Software, Booz Allen Hamilton, and Deloitte, with a focus on scaling teams and driving organizational growth.
Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
I didn’t start my career in HR, it was a role I evolved into with intention. My first professional endeavor was in consulting, working at Booz Allen Hamilton and Deloitte on organizational transformation and change management. That work laid a strong foundation for understanding how businesses tick, how people adapt to change, and how culture drives outcomes. Over time, I realized that the heart of any company is its people, and I wanted to be closer to that.
From there, I transitioned into people leadership roles at high-growth companies like Greenhouse, where we earned a top spot on Glassdoor’s Best Places to Work, and Jetblack, a Walmart company, where I helped scale the team from 20 to 350 in under two years. I later became Chief People Officer at Heap, which was acquired by Contentsquare in 2023. Now at Contentsquare, I’m responsible for leading our global people strategy, creating environments where high-performing, engaged teams can thrive.
Can you share the most interesting story that happened to you since you began working with remote or hybrid teams?
Rather than highlight a single story, I want to share an overarching theme: remote work unlocked access to talent we hadn’t tapped into before. Expanding our talent pool globally has significantly increased our ability to drive impact, bringing in fresh perspectives, deeper expertise, and capabilities that simply weren’t available to us in a more location-bound model.
A colleague of mine was from North Macedonia, and their unique background and approach added fresh insight to problem-solving. It underscored a bigger truth: that global hybrid teams aren’t just about distributed headcount, they’re about distributed thinking. The acquisition of Hotjar, a fully remote company with employees in over 50 countries, deepened this learning. It opened the door to more perspectives, more voices, and richer problem-solving.
Rather than just focus on collaboration, we’ve leaned into the diversity of thought that naturally emerges from this kind of global structure. It’s not just about different time zones anymore; it’s about different ways of thinking, working, and relating to customers. That’s been an incredibly rewarding and interesting part of leading in a remote world.
Let’s now dive into the focus of our interview. When the shift to remote work became widespread, what was the biggest challenge you faced in maintaining a strong workplace culture? How did you address it?
Contentsquare naturally had a strong in-office culture, so transitioning to a fully remote setup required thoughtful planning. Through this, the biggest challenges were engagement and collaboration. We didn’t want to lose the sense of connection just because we were no longer physically together. That meant rethinking how we engage and collaborate, both asynchronously and synchronously.
We introduced structured “Ways of Work” toolkits with templates for meetings, business cases, and workshop facilitation. We encourage informal connections too, like using Slack as a virtual office where people can share morning greetings, just like you would walking into a real office. Leaders set the tone by modeling this behavior; that’s why I always start the week off by sharing a few photos and a download of my weekend with my team, and I encourage them to do the same.
We also allocated team-level budgets for virtual fun. Everything from online happy hours to group walks while on a call. And crucially, we made space for in-person time with regular meetups. It’s about mixing intention with spontaneity, so the culture doesn’t feel forced, but also doesn’t drift.
What role does leadership play in building and sustaining a strong company culture in a remote or hybrid work environment?
Leadership sets the tone, plain and simple. In a remote world, where people don’t pick up on casual cues from hallway chats, leaders have to be even more deliberate. Every message, meeting, and decision becomes a cultural signal. That’s why I emphasize intentionality — be thoughtful about how you show up and how you engage. Whether that’s signaling an in-office day to your team or setting the tone through everyday Slack interactions.
One impactful program we have at Contentsquare is our Leadership Q&A Fireside Chats, where executives answer employee questions live. It creates transparency, but more importantly, it humanizes leaders and makes them more accessible. These informal forums are well received because they break down hierarchy and foster trust, two things that are harder to build remotely but are absolutely essential.
Based on your experience, can you share “5 Strategies to Build a Strong Workplace Culture in a Remote Work Environment”?
Absolutely. Here are five strategies that have worked for us:
1. Define a working culture: Establish clear working principles and responsibilities across teams and time zones. If you’re vague about expectations, misalignment will creep in fast.
2. Be intentional with communication: Don’t just send out messages; think about how they’re received. Cascading change effectively in a remote world requires applying solid change management principles. That includes clarity, repetition, and multiple formats: written, visual, and live.
3. Enablement: Take advantage of company resources and technology to enable your team and ensure you’re upskilling managers.
4. Invest in the right tools: We rely heavily on Slack, Google Docs, and other collaboration and communication tools. What matters most is that the tools empower self-service and transparency, while also offering readily available resources.
5. Create equitable office and remote experiences: Recognize different employee personas. What a remote employee needs may differ from what an in-office team member needs. Equity doesn’t mean identical; it means fair. That could mean remote stipends, hybrid flexibility, or different types of engagement budgets
Can you share an example of a remote work initiative, policy, or program that you implemented which had a significant positive impact on your team?
One standout initiative was our recent week-long, off-site gathering in Berlin, “CSQuest”. This brought together employees from Heap, Hotjar, and Contentsquare to align teams on the CEO’s vision, company strategy, and product roadmap. A big part of what made CSQuest successful was that everyone across the leadership team understood the magnitude of the rekindled human connection. We were equally focused on discussing the business as well as empowering connections between employees (our ‘CSquad!). Just spending time together in person gave everyone a jolt of energy. It wasn’t just productive, it was inspirational. People left recharged, reconnected, and reinvested in our mission.
That one week did more than dozens of Zoom meetings ever could. It reminded us that while remote work is powerful, human connection still matters, and creating space for it pays dividends in motivation and performance.
In your opinion, how does building a strong culture in a remote work environment impact not just employees, but also customers, clients, and the company’s overall performance?
There’s a direct line between employee experience and customer experience. If your people are motivated, connected, and valued, that radiates outward. We aim for our employee engagement score to be just as strong as our customer satisfaction score, because they’re intrinsically linked.
When leaders show up authentically and employees feel empowered to do their best work, it creates a ripple effect. High-performing teams deliver better products. They support clients more effectively. And they build a brand that people trust, not just because of what you do, but because of how you do it.
How can our readers further follow you online?
Readers can connect with me through LinkedIn: https://www.linkedin.com/in/melanie-oberman-4b612b9/
This was great. Thank you so much for the time you spent sharing with us.
About the Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.
The Remote Work Revolution: Melanie Oberman Of Contentsquare On Building Strong Cultures in a… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.