Contentsquare Names Chip Winslow as Americas Chief Revenue Officer and Orly Lynn as VP Head of Diversity, Equity & Inclusion

Former Splunk and HSBC Executives Join Contentsquare to Oversee Revenue Stream Growth and Continued Investment in DE&I Initiatives

NEW YORK–(BUSINESS WIRE)–Contentsquare, the global leader in digital experience analytics, announced today that Chip Winslow and Orly Lynn have joined the company to lead global efforts in revenue growth and Diversity, Equity and Inclusion. Both Chip and Orly bring a wealth of knowledge and experience to their respective roles, and will be critical to Contentsquare’s next phase of growth.

Chip Winslow, Americas Chief Revenue Officer

Following a $500M Series E funding round in May, Contentsquare’s leadership began looking to add key executives to support the company’s path towards market dominance on a global scale. Chip, a former growth executive at Splunk, will lead the Americas Sales organization. Chip’s hands-on, collaborative but driven leadership style, and focus on customer value will be pivotal to the sales team’s success. He will support Contentsquare’s current corporate strategic plan, and oversee expansion to new customer segments and partnerships in the Americas, while ultimately strengthening operations by closely collaborating with other key groups like marketing and product development.

Most recently, Chip served as the Group Vice President, America’s Commercial and Digital Sales at Splunk. Under his leadership, Splunk achieved 100% year-over-year ARR growth for several years in a row, leading a 300+-strong organization. Prior to Splunk, he held leadership positions at Echidna, a digital commerce software company, and MotionPoint, the World’s Leading Digital Business Globalization Platform, as well as VP and AVP positions at Elastic and Oracle. His 25+ year career in enterprise sales and revenue and field operations management has generated a proven track record in all aspects of sales, marketing, business operations and international expansion.

“It’s an exciting time for Contentsquare. The momentum it’s built and the success it’s achieved during rapid business and solutions expansion, globally, isn’t something you see every day,” said Chip. “The next couple of years are critical to Contentsquare’s story and its mission to help brands create and deliver data-powered customer experiences. I’m excited to be a part of this important next phase for the business, and during a revolutionary time in digital marketing overall. With an intense laser focus on intentional growth strategies, Contentsquare will continue to lead this market into the next era. Its work will define the future of digital relationship management as we know it, and help brands reimagine the way they view, understand and leverage CX data to deliver experiences of tomorrow, today.”

Orly Lynn, VP and Head of Diversity, Equity and Inclusion

With company plans to add 1,500+ jobs in the next three years in full swing, maintaining a positive and productive workplace environment and culture that recognizes and celebrates diversity, equity and inclusion are of utmost importance. Under Orly’s leadership, Contentsquare will continue its commitment to creating opportunities that are accessible to all, adding to the company’s already-inclusive culture.

With the past eight years of her career dedicated to DE&I, Orly has helped organizations develop the competencies needed to cultivate cultures of inclusion and equity. Her robust knowledge and institutional awareness of the challenges and opportunities organizations encounter as the workforce changes has led her to develop creative programs where all employees are seen, heard, valued and supported. With stints at HSBC, Credit Suisse, Commvault, Orly’s expertise in internal education on DE&I matters and people-first program development will be extremely valuable to Contentsquare during its meteoric growth. Most recently, Orly served as a diversity consultant with her own practice, Diversity Unfiltered.

“Contentsquare’s leadership has done a phenomenal job at creating a corporate culture that celebrates the contributions of everyone that makes up this very unique brand, which is no small feat,” said Orly. “Formalizing DE&I as a priority program is a strong demonstration of leadership’s commitment to its team and the value each individual brings. I’m thrilled to be a part of that journey and look forward to helping cement Contentsquare’s strong cultural foundation.”

“Having Chip and Orly be a part of Contentsquare’s growth has filled us with excitement and enthusiasm,” said Jonathan Cherki, Founder & CEO of Contentsquare. “Chip brings a wealth of expertise and will play an integral role in scaling our company’s growth in the Americas, while Orly’s vast experience in DE&I leadership will be key to driving diversity and inclusion at Contentsquare. Their energies complement the company’s culture very well and I have no doubt their contributions and strategic expertise will help us deliver customer experience solutions better and faster, ultimately transforming the way brands do business online.”

About Contentsquare

Contentsquare empowers brands to build better digital experiences. Its experience analytics platform tracks and visualizes billions of digital behaviors, delivering intelligent recommendations that everyone can use to grow revenue, increase loyalty and fuel innovation. Founded in Paris in 2012, Contentsquare has since opened offices in London, New York, San Francisco, Munich, Tel Aviv, Tokyo, Singapore and Barcelona. Today, it helps more than 750 enterprises in 26 countries deliver better digital experiences for their customers. Visit to find out more.


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Ben Rees/Fiona Todd at Wildfire PR


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