Contentstack, the headless CMS pioneer and category disruptor in digital experiences, today announced Josette Leslie as its new Chief Financial Officer. Based in New York City, Leslie brings over 25 years of financial leadership experience across the content management, fintech, and banking sectors and is skilled in translating operational decisions into financial outcomes while driving company and stakeholder value. Leslie spent seven years at Squarespace, where she helped scale finance operations and support the company’s IPO in 2021.
She replaces David Overmyer, who was part of the original leadership team at Contentstack and helped scale the company to $169 million raised. Overmyer is retiring from his executive role and will continue to serve on Contentstack’s Board of Directors.
Leslie will report to Neha Sampat, founder and CEO of Contentstack. “Josette brings a rare combination of deep industry understanding, operational insight for fast-growing SaaS companies like Contentstack, and a values-driven leadership style that aligns with our culture,” said Sampat. “Her proven track record of delivering results with strategic vision, strong leadership, and a positive culture will be invaluable as we continue to grow Contentstack and drive the market forward.”
“I’ve seen firsthand how financial and operational excellence can accelerate innovation, and that’s the edge I see in Contentstack,” said Leslie. “But what ultimately drew me to Contentstack was the caliber of the team and its mission to modernize digital experiences and empower people to do their best work. I look forward to working alongside the team and playing an integral role in shaping that future.”
Leslie most recently served as CFO at CAIS, an alternative investment platform for independent financial advisors. As CFO of Affinity, an enterprise CRM platform, she led the company through rapid growth and operational maturity. Her earlier career accomplishments include experience at E*TRADE Financial in various leadership positions within brokerage finance and five years at Instinet, where she managed financial planning and analysis functions supporting its IPO.
Leslie also serves on the Board of Directors of Women in Innovation, a nonprofit empowering women as innovators and changemakers, as the treasurer and chair of the audit and finance committee.
The hire follows a fast-paced start to Contentstack’s fiscal year, with the acquisition of Lytics, a real-time Customer Data platform, to accelerate its position as a DXP leader. Subsequently, the company was named a Visionary in the 2025 Gartner® Magic Quadrant™ for Digital Experience Platforms report and ranked number 19 on Forbes’ 2025 List of America’s Best Startup Employers.
Next week, Contentstack will host its fourth-annual customer conference, ContentCon, exploring how the convergence of content and data powers real-time personalization at scale for the world’s leading brands.
About Contentstack
Contentstack is on a mission to deliver the world’s best digital experiences with cutting-edge content management, customer data, personalization and AI technology. Iconic brands such as Air France-KLM, ASICS, Burberry, Mattel, Mitsubishi and Walmart depend on the Contentstack EDGE platform to rise above the noise in today's crowded and competitive markets, constantly adapting to maintain their edge.
Contentstack and its employees are dedicated to the customers and communities they serve. The company is recognized for its unmatched customer care and tradition of giving back globally through the Contentstack Cares program, including proud support of Pledge 1% and Girls Who Code.
