HRTech Interview with Melanie Oberman, Chief People Officer at Contentsquare

We’re delighted to have you at HRTech Cube, Melanie! To start, could you share a bit about your professional journey and what led you to your role as Chief People Officer at Contentsquare?
Thank you for speaking with me! Early in my career, I was a consultant at Booz Allen Hamilton and Deloitte, where I specialized in organizational transformation and change management in both roles. These consulting experiences have shaped how I operate in the People space, contributed to my success in scaling companies, and they were integral building blocks to the next part of my career as a people leader. I’ve had leadership roles at leading tech companies including Greenhouse, Jetblack and of course, Heap. At Greenhouse, my work was instrumental in taking the company to the #1 spot on the Best Places to Work list on Glassdoor. I am proud to share that in my role at Jetblack, I grew the team from 20 to 350 in less than two years. Most recently at Heap, we were awarded Best Places to Work on Glassdoor. In December 2023, Heap was acquired by Contentsquare, and I’m thrilled to be leading the people function of such a dynamic, growing team!

With your experience in leading cultural integration across multiple acquisitions, what strategies have you found most effective in preserving a unified culture across global teams?
Cultural integration can be a misunderstood concept, often associated with compromise. However, it can be a unique opportunity to maximize the strengths of each organization. Rather than diluting or discarding individual cultures, focus on identifying common values, missions, and unique traits that can be woven together to create a stronger, more unified culture. Cultural integration is about leveraging the strengths of multiple organizations rather than diminishing single identities. It involves a harmonious blending of distinct characteristics, ensuring that the unique aspects of each company are preserved while creating something even more impactful together.

As Contentsquare scales rapidly, how do you ensure that core company values remain at the heart of growth and expansion efforts?
As Contentsquare continued to scale, we had to first ensure that our values reflected our new company, incorporating Contentsquare, Heap and Hotjar. We redefined our values as part of scaling our new brand, focusing on who we are and who we want to become.

Most companies tend to look for culture fits. We look for culture adds, which goes hand-in-hand with aligning our values. Incorporating a “culture add” interview as part of our hiring process allows us to not only hire people aligned with our values but also allow room for diversity of thought and experience. By prioritizing cultural alignment over cultural homogeneity, we believe new hires are more likely to engage positively with their teams, leading to better collaboration and a more cohesive work environment. This approach can also reduce turnover rates, as employees who resonate with our culture tend to stay longer, ultimately saving costs associated with recruitment and training​. This is especially important when maintaining a strong culture across teams, both globally and from previous acquisitions, and it’s allowed us to create an environment where everyone can unlock their full potential and bring their best self to work. Our team members focus on delivering excellence for our customers, our partners and our teams.

Could you explain the approach Contentsquare uses to implement company behaviors that align with its core values and contribute to an authentic workplace culture?
Rapid growth should not compromise a company’s culture; rather, it should serve as a catalyst for enriching it. We’ve built an environment that actively invites feedback, empowering our employees to voice their thoughts and concerns. This openness not only deepens trust across the organization but also fosters a resilient culture that can flourish amidst rapid change. Although our values may remain fairly constant over time, the behaviors and habits that underpin them can flex based on changing employee and business needs.

How do you connect the company’s mission to talent attraction and retention strategies to foster long-term engagement among employees?
Enhancing employee well-being is directly correlated with improving customer experience. At Contentsquare, we empower businesses to create a world where everyone gets the experience they love, seek and deserve. In turn, we believe that when employees are empowered and fulfilled, they naturally convey that enthusiasm to our customers. Satisfied employees not only deliver better service but also reflect the company’s values, thus strengthening customer trust and brand loyalty.

We make sure our employees feel comfortable, wherever they may be in life. We want to not only bring in and retain the best talent, but also foster an inclusive workplace culture where everyone–regardless of their background or identity–can bring their best selves to work every day.

Some examples of employee programs that we’ve implemented, to help keep our employees happy and retained, include:

• Flex Return-from–Birthing/Non-Birthing Leave Option to ease new parents’ transition back to work (5 PTO days)
• Compassionate Leave for Reproductive Loss: Up to five days of compassionate leave following a reproductive loss event.
• Our 16 Weeks for birthing and non-birthing leave now also includes adoption and surrogacy, where legally feasible.
• Family Care Leave: Our child sick leave policy was extended from 3 to 5 days per year and expanded to include broader caregiving responsibilities.
• Wellbeing Allowance, which can be applied to caregiving support (e.g. lactation or sleep consultants for new parents).
• Plumm resources, which include therapy and coaching, chat support, and resources specifically for parents and caregivers.
• Parents and Caregivers Resource Hub is available for employees at any time.

You’ve championed the LEAP model for people development. Can you share how this model supports high-performance cultures and advances success for CPOs?
My vision is to create an unparalleled people experience that attracts and retains top talent and fosters a culture of innovation and inclusivity. To do this, I’ve focused on what I call the LEAP Model:

• Leadership: Enable great leaders to drive growth in others, achieve company success, and establish thought leadership
• Engagement: Engage the team through feedback, accountability, and clarity of purpose.
• Authenticity: Build an inclusive workplace where the team feels safe and empowered to bring their best selves to work every day
• Performance: Develop a high-performance culture that attracts, recognizes and retains top talent

I encourage other Chief People Officers to follow a similar method. The LEAP Model is a structured framework that I’ve developed to create an exceptional people experience and drive organizational success. The LEAP Model is more than a set of guiding principles—it’s an actionable strategy that aligns people development with business goals. For CPOs, adopting a similar approach ensures that your people initiatives are purposeful, scalable, and deeply integrated into the organization’s success.

“I encourage all people leaders to make sure there is a clear focus in their organizations on embedding inclusivity in everything they do. For us, it’s apparent in our hiring practices, compensation & benefits, talent development and performance processes, ways of working, and more. When we cultivate an inclusive foundation for our people, we bring in the best talent and truly benefit from the diversity of our team.”

What are some key elements you consider essential for building leadership development programs that can scale with the organization?
At Contentsquare, we are deeply committed to growing our internal talent and empowering employees to take charge of their career development. To support this at scale, we consider several key areas:

Empowering Employees to Own Their Growth: We believe development is most impactful when employees are engaged and motivated to invest in themselves. To meet them where they are, we offer a wide range of growth opportunities tailored to different career stages and learning modalities. This includes an established internal mobility policy to enable vertical, lateral, and diagonal career moves, and we actively promote our internal job board to regularly facilitate career transitions.

Scalable Learning and Development Programs: Our global leadership development programs are designed to support leaders at every stage—from aspiring managers to senior leaders and executives. We balance in-house expertise, such as mentorship programs, masterclasses, and collaborative workshops, with strategic partnerships like CoachHub to offer expert coaching, as well as on-demand courses through Udemy, and bespoke leadership development opportunities.

Structured Development Processes: We’ve formalized Professional Development Planning (PDP), ensuring employees set motivating goals and are encouraged to dedicate time to their personal and professional growth. This process helps align individual aspirations with organizational needs, creating a culture of continuous growth and development.

As AI is introduced in the workplace, what are your views on its role in shaping high-performance cultures, and what do you see as the main challenges and opportunities for people leaders and employees?
Technology is evolving quickly with the adoption of AI. These changes present many opportunities for innovation. To stay on top of these changes, and to ensure these new technologies are deployed in safe, ethical, and effective ways, we need diverse teams working on them. Contentsquare’s talent team has been hard at work with our Information Systems Department (ISD) ensuring employees understand how AI plays a role at work. These include understanding ideas directly related to Contentsquare’s product, such as how AI will disrupt traditional analytics and why you don’t necessarily need a PhD in analytics to understand products including CoPilot. Our team members know that AI will impact and help optimize tasks across the people team, product, technology, customer support, marketing and more – it’s clear that AI goes beyond solely our company’s mission, but really comes alive in an individual’s direct job function.

In a 2024 survey of 250 Contentsquare employees, 1 out of 3 employees shared they wish to master AI in the context of their next role. Our employees are truly driven by AI, and I imagine that this number has only grown since we issued the survey earlier this year. I’m curious to see where AI takes us. So far, we’ve implemented AI throughout work by giving all employees Atlassian AI on Confluence and a flank bot on Slack to help them find and generate content more easily. Across departments, we’ve also been experimenting with Fireflies, Miro, Gemini AI, the AI in Zendesk, Jira Service Management, and HeyGen. Most recently, we released key AI learning tools for employees, including an ongoing course on using generative AI responsibly, and a generative AI calendar designed to help employees become experts on AI. Each day, they can access engaging content—videos, training modules, and articles—all aimed at enhancing their understanding of AI and its applications at work. At the end of the 21 days of content (based on Maxwell’s habit-building philosophy that 21 days is the perfect amount of time to build a consistent learning routine and develop foundational AI skills), they earn a certificate of achievement.

On a personal level, what core strategies have helped you succeed in aligning workplace policies, feedback loops, and employee engagement with overall business objectives?
When people consider the relationship between employee experience and customer experience, they may hear a lot about the correlation between the two–the happier your employees, the happier your customers. What they don’t hear a lot about is how they can actually look to great customer experience as a model for great employee satisfaction.

Throughout my work at SaaS companies, I’ve learned to run the people team like a product team: similar to how we focus on delivering an amazing customer experience for top brands, my team focuses on delivering an amazing people experience. We do this through a strategic, proactive, and employee-centered approach that borrows best practices from how product teams operate.

This has certainly helped us succeed with initiatives such as feedback loops. As product teams have mechanisms to gather user feedback (surveys, focus groups, etc.), the People team has regular feedback channels to assess employee satisfaction, engagement, and areas for improvement. These include listening tours, engagement surveys, and exit interviews, among others.

In addition, in the rapidly evolving world of work, and particularly for SaaS companies, flexibility has become a non-negotiable requirement for both employees and employers. The pandemic catalyzed the shift to flexible working models, and companies that adapt will be better placed to attract and retain talent. Success now hinges on fostering environments that accommodate diverse work preferences while maintaining productivity. To enable seamless collaboration, it’s critical that alongside investing in new tech, teams operate with consistent working norms.

At Contentsquare we established a dedicated program team to understand our diverse employee needs, before defining and rolling out company-wide working practices. This initiative aims to enhance productivity by setting consistent expectations for communication, workflows, and decision-making. The future of work is not just about where people work, but how they work together.

Finally, any advice for fellow people leaders on fostering a resilient and adaptable culture in today’s rapidly evolving work environment?
I encourage all people leaders to make sure there is a clear focus in their organizations on embedding inclusivity in everything they do. For us, it’s apparent in our hiring practices, compensation & benefits, talent development and performance processes, ways of working, and more. When we cultivate an inclusive foundation for our people, we bring in the best talent and truly benefit from the diversity of our team. Another example of a strategy that works to foster an adaptable culture is leveraging Employee Resource Groups (ERGs) as drivers of our inclusive culture. ERGs are designed to provide safe spaces for employees and play a strategic role in ensuring the business considers diverse perspectives across key initiatives.