One Size Fits None with Jenny Hadlow, COO of Checkout.com
Jenny Hadlow's journey from Yext to running a $20B fintech company, and her revolutionary approach to continuous feedback that's transforming organizational culture.
This was a lot of fun. Jenny Hadlow and I have had the pleasure of working together for over a decade at Yext. Watching her grow into an incredible executive and now running a $20B company in Checkout.com is one of the joys of my career.
From Startup to Scale: Jenny’s Career Evolution
Jenny’s journey represents one of the most impressive career trajectories I’ve witnessed in the tech industry. When we first worked together at Yext, she demonstrated an exceptional ability to navigate complex challenges while maintaining her clear vision for growth. Her progression from those early days to leading one of the world’s most valuable fintech companies showcases the power of continuous learning and adaptive leadership.
At Yext, Jenny was instrumental in building scalable processes that could handle rapid growth. She understood early on that successful companies don’t just need great products—they need leaders who can evolve their management style as the organization scales. This insight would prove invaluable as she transitioned to the fintech world.
Building a $20B Company: The Checkout.com Story
Checkout.com’s rise to a $20B valuation didn’t happen overnight, and Jenny’s leadership has been central to this remarkable growth. The payments industry is notoriously complex, with regulatory challenges, technical complexity, and fierce competition. Yet under Jenny’s guidance, Checkout.com has not only survived but thrived in this environment.
Her approach to building teams at scale is particularly noteworthy. Managing a company of Checkout.com’s size requires a fundamentally different set of skills than running a smaller operation. Jenny has had to master the art of maintaining company culture while expanding globally, ensuring that the startup agility that made Checkout.com successful doesn’t get lost as the company grows.
Revolutionary Approach to Feedback
What Jenny does around feedback shocked me during our conversation. Most executives treat feedback as a formal, scheduled process—annual reviews, quarterly check-ins, structured performance conversations. Jenny has completely reimagined this approach.
Instead of waiting for formal feedback cycles, she’s created a culture where feedback flows continuously and organically throughout the organization. Her team uses real-time feedback mechanisms that capture insights in the moment, when they’re most relevant and actionable. This approach has transformed how her organization learns and adapts.
The results speak for themselves. Teams under Jenny’s leadership report higher engagement, faster problem resolution, and more innovative solutions. By removing the friction from feedback, she’s created an environment where continuous improvement isn’t just encouraged—it’s embedded in the daily workflow.
Listen to the Full Conversation
Hear from Jenny on her career journey and how she runs her organization today. What she does around feedback shocked me! 🎧👇
Listen on your favorite platform:
- Spotify - Stream the full interview
- YouTube - Watch the video conversation
- Apple Podcasts - Listen on Apple Podcasts
Interested in learning more about revolutionary feedback approaches? Request a demo to see how Windy can help transform your team’s feedback culture.