Contentstack taps a powerhouse CFO to fuel its next wave of growth. Here’s why it matters

CFOs are having an evolutionary moment, particularly in the realm of digital transformation. 

I’ve been tracking this shift for quite some time, talking to leaders on both the vendor and customer side, and it's clear that the role is expanding beyond financial functions to encompass deeper data analysis, risk management, and broader company strategy. 

This change has been driven by a myriad of factors, including increased global risk, economic volatility, and a surge in new technologies like AI. But there’s also been a precipitous expansion on the composable side of the DX ledger, where CFOs are increasingly tasked with being more informed about the tech composition of modern stacks to help support better decisions.

That brings us to some key news about Contentstack – which is, by all measures, on a roll. After the company’s sage acquisition of Lytics in January, the composable DXP found itself in the Leaders sphere of the 2025 Forrester Wave for Content Management Systems, validating its strategic roadmap. 

Now, in a move that signals more than just another executive appointment, Contentstack has hired Josette Leslie as its new Chief Financial Officer. And if we're reading the tea leaves, this calculated maneuver suggests the company might be gearing up for some bigger market moves.

“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 replaces David Overmyer, who was part of Contentstack’s original leadership team. During his tenure, he was instrumental in helping to raise $169 million and scale to an industry powerhouse. Overmyer is retiring from his executive role and will continue to serve on Contentstack’s Board of Directors.

Evolving beyond the balance sheet

As I said, today’s CFO is as much a strategic growth architect as a financial steward. To that end, Leslie’s appointment is a bold, throat-clearing moment that suggests Contentstack is not only doubling down on its ambitions but rewriting the CFO’s role in a modern digital enterprise.

Leslie brings a serious pedigree to the table. With more than 25 years of experience – including high-impact roles at Squarespace, E*TRADE, and Instinet – she’s no stranger to guiding companies through hyper-growth, IPOs, and operational scale. At Squarespace, she helped shepherd the company through its 2021 IPO, proving she can navigate the complex terrain of fast-scaling SaaS platforms with poise and precision.

Her new post at Contentstack comes at a pivotal moment. The company is riding a wave of momentum after acquiring Lytics, which added a critical real-time customer data component to its DXP composition. Add in Contentstack’s recognition as a Visionary in the 2025 Gartner Magic Quadrant for DXPs – and its #19 spot on Forbes’ 2025 List of America’s Best Startup Employers – and you get a sense that the company is running on rocket fuel. 

Leslie is building her vision on a solid foundation. In her experience, she’s seen firsthand how financial and operational excellence can accelerate innovation and unlock value. “What ultimately drew me to Contentstack was the caliber of the team and its mission to modernize digital experiences,” she said.

Why it matters

Contentstack's CEO Neha Sampat has praised Leslie’s knowledge, insight, and values-driven leadership style – and rightly so. Given her previous successes in acquisitions, change management, and business revitalization, she brings an unmatched acumen and a tight integration of finance, operations, and go-to-market execution to the table.

Let’s not forget that Contentstack is a composable platform, built on modularity and scale. In this space, the role of the CFO is uniquely positioned to bridge the gap between financial performance and platform agility. Leslie’s arrival could signal a more aggressive approach to expansion, M&A, and infrastructure investment, especially as the industry accelerates toward real-time personalization and AI-powered experiences.

There's also the new vision that Contentstack has been piloting around “adaptive digital experiences,” which is crystallized by its new Contentstack EDGE offering. This new breed of adaptive DXP combines intelligent content and real-time, first-party customer data, courtesy of the new Lytics CDP acquisition. 

Leslie's tech prowess could be a key activator for propelling EDGE to the forefront. The platform’s ability to react in real time to every customer interaction while staying authentically on-brand through AI and data-driven decision-making could be the new model for marketers and brands that rely on their DXP tools to be fast, elegant, and designed for AI. Hence, it's likely a central initiative for the leadership team. 

With ContentCon just around the corner, the timing is clearly intentional as Contentstack builds hype and energy around its announcements. The annual conference will no doubt set the stage for what’s next in the convergence of content, data, and personalization at scale. 

One thing’s certain: With Josette Leslie at the financial helm, Contentstack isn’t just building a future-proof platform. They’re financing the future of digital experiences. And given her wealth of wisdom, she has a clear view of the chessboard – and where to move the pieces.

Looking for guidance on Contentstack? Talk to an expert.

Upcoming Events

Contentstack ContentCon 25

June 3-5, 2025 – Chicago, USA

The future of digital is waiting for you! Contentstack presents ContentCon, the premier event for digital teams and industry leaders who are reimagining the future of digital experiences. Join us for two days of transformative presentations and workshops designed to help you put personalization and AI strategies into action. Register today! 

CMS Connect 25

August 5-6, 2025 – Montreal, Canada

We are delighted to present the second annual summer edition of our signature global conference dedicated to the content management community! CMS Connect will be held again in beautiful Montreal, Canada, and feature a unique blend of masterclasses, insightful talks, interactive discussions, impactful learning sessions, and authentic networking opportunities. Join vendors, agencies, and customers from across our industry as we engage and collaborate around the future of content management – and hear from the top thought leaders at the only vendor-neutral, in-person conference exclusively focused on CMS. Space is limited for this event, so book your seats today.