Bengaluru: Contentstack, a headless CMS and digital experience platform, has announced the appointment of Josette Leslie as its new Chief Financial Officer (CFO). Based in New York City, Leslie brings more than 25 years of financial leadership experience, including senior roles at Squarespace, E*TRADE, and CAIS, to steer Contentstack through its next phase of global growth and market expansion.
Leslie succeeds David Overmyer, a founding member of Contentstack’s leadership team, who helped guide the company to over $169 million in funding. Overmyer will retire from his executive role but continue to serve on the company’s Board of Directors.
A seasoned finance executive, Leslie played a critical role at Squarespace during its transformation and IPO in 2021. She brings a strong background in financial operations, strategic planning, and driving enterprise value for fast-growing SaaS companies.
“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 Neha Sampat, Founder and CEO of Contentstack. “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.”
Leslie most recently served as CFO at CAIS, a leading alternative investment platform for financial advisors. She has also led finance operations at Affinity, an enterprise CRM platform, and previously held leadership roles at E*TRADE Financial and Instinet, where she helped guide both companies through IPO and expansion phases.
“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.”
In addition to her executive career, Leslie serves on the Board of Directors for Women in Innovation, a nonprofit dedicated to advancing women as innovators and changemakers. She currently chairs the audit and finance committee and serves as the organization’s treasurer.
This leadership transition comes during a strong start to Contentstack’s fiscal year. The company recently acquired Lytics, a real-time customer data platform, to bolster its position as a leader in Digital Experience Platforms (DXP). Contentstack was also named a Visionary in the 2025 Gartner® Magic Quadrant™ for DXP and ranked #19 on Forbes’ 2025 List of America’s Best Startup Employers.
Next week, Contentstack will host its flagship event, ContentCon, bringing together global brands and digital leaders to explore how the convergence of content and data enables real-time personalization at scale.
