Aon at The Top: Interviewing Executives on their Paths to the C-Suite and Boardroom

Greg Henry joins Aon at the Top to discuss his journey from Milwaukee to becoming CFO of 1Password, one of the fastest-growing cybersecurity companies. We dive into the "million dollar experiences" that shaped his career, from an FDA consent decree that shut down his first CFO role to the 2018 moment at Couchbase when he and the CEO were "staring over the abyss," facing the possibility of running out of money. Greg reveals his strategy-structure-people framework for building organizations, explains why he evolved from being "CFO No" to "CFO Go," and shares how trust beats control when it comes to financial planning.

In this episode of Aon at the Top, I sit down with Rachana Kumar, a trailblazing global CTO, product executive, and board director with more than two decades of experience shaping the future of technology and scaling hypergrowth organizations. We dive into what it means to lead through a business turnaround, how to balance data with intuition, and why the best career advice she ever received was "don’t reject an opportunity before it exists."Timestamps:00:09:33 - Being the first generation of women in her family to work outside the home00:14:33 - The 2017 Etsy turnaround00:19:18 - Building Etsy's culture of innovation00:27:09 - Balancing data-driven decisions with intuition while staying connected to 1,200+ people00:34:01 - Leading responsible AI at Etsy00:42:14 - The best career advice she ever received00:47:25 - How to lead through uncertainty00:56:14 - Her 9-year-old son's question: "What do you want to be next?"Connect with Rachana on LinkedIn: https://www.linkedin.com/in/rachanakumar/About Rachana Kumar:Rachana Kumar is a global CTO and product executive with more than two decades of experience leading high-impact innovation, scaling hyper-growth organizations, and driving transformation in e-commerce, media and entertainment companies. Most recently as Chief Technology Officer at Etsy, Rachana led a sweeping AI and platform transformation, driving 5x adoption of generative AI, ensuring 99.95% uptime, and powering over $13 billion in annual sales and $2.8 billion in revenue. She managed global teams of more than 1,200 people, oversaw P&L responsibilities exceeding $1 billion, and expanded Etsy's global footprint as Managing Director of Etsy Mexico. She serves on the board of trustees for the Liberty Science Center and as a Tech Advisory Council member at the Lincoln Center for the Performing Arts.Connect with Nicole: Stay connected with Nicole Ward for more insights on leadership, sales excellence, and executive success strategies.Connect on LinkedIn: https://www.linkedin.com/in/nicoleward111/Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/aon-at-the-top-interviewing-executives-on-their-paths/id1800795612Listen on Spotify: https://open.spotify.com/show/0L46j1vJo79LQC4LViO2KOSubscribe to "Aon at the Top" to hear more conversations with distinguished executives, CEOs, and board members as they share their paths to success and leadership insights.

In this episode of Aon at the Top, I sit down with Caroline Tsay, a tech leader, builder, and public company board director who has scaled businesses, launched startups, and guided major companies strategically and operationally. Caroline has done everything from leading teams at Yahoo and Hewlett Packard Enterprise to co-founding and running her own company to serving on some of America's most highly visible boards. We dive into why the hardest initiatives create the best opportunities, the fine line between board oversight and operational interference, and why strategy without execution is just a hallucination.

In this episode of Aon at the Top, I sit down with Yasmin Saeed Coffey, Chief Legal Officer and GM of Distribution at TuneIn, one of the world's largest audio streaming platforms. Yasmin's career spans entertainment powerhouses like Paramount Pictures, litigation across multiple industries, and now leading global licensing strategy in the fast-moving world of digital media. We dive into why saying yes before you're ready has been her career accelerator, how she balances risk mitigation with the speed required in streaming media, and what it takes to pivot across industries without a traditional pedigree.

In this episode of Aon at the Top, I sit down with Derrick Alesevich, a C-suite executive who's spent two decades building unicorn technology companies in Silicon Valley, to uncover what it really takes to lead legal teams through hyper-growth, billion-dollar acquisitions, and the chaos of early-stage startups. We dive into the stark choice every in-house attorney faces that determines their entire career trajectory, why transparency and communication matter more than perfection at early stage, and the hidden cost of hiring legal counsel too late.

In this episode of Aon at the Top, I sit down with Shanti Ariker, Chief Legal Officer at JFrog, to explore her unconventional journey from witnessing her parents' custody battle as a child to leading global legal strategy for one of the world's most trusted DevOps platforms. We dive into why taking six years off work became pivotal to her career, how she transformed legal departments from "the department of no" to solution-oriented business partners, and the moral courage it takes to speak up when the legally safe answer isn't always the right answer.