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

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.

In this episode of Aon at the Top, I sit down with Yvonne Wassenaar, accomplished board director and former CEO, to explore her remarkable journey from Accenture partner to leading technology companies through transformation. We dive into the three distinct phases of her career, the personal tragedy that reshaped her life at 36, and the critical leadership lessons she learned about vulnerability, honesty, and making calculated risks. Yvonne shares candidly about how executive coaching evolved into therapy, helping her become a more grounded leader who now guides some of tech's most prominent companies.Timestamps: 3:22 - The three phases of career growth: being pulled up, pushed out, and embracing risk4:36 - You get promoted because you make people above you successful8:03 - Being pushed to get startup experience before 509:51 - The ski jump analogy12:33 - Resilience is fighting through hard times for something that matters19:23 - None of us really know what we're capable of until the time calls upon us25:02 - During uncertainty, we make the hardest decisions27:43 - Leading through chaos30:05 - The rise of independent directors in private companies32:02 - The difference between being an operator vs. a strategic advisor on boards40:41 - Separate your emotion from someone's intentionality to get further in life43:00 - Making hard CEO decisions: when to break teams out to innovate faster58:22 - The power of many small decisionsConnect with Yvonne on LinkedIn: https://www.linkedin.com/in/yvonnewassenaar/About Yvonne Wassenaar: Yvonne Wassenaar is an accomplished CEO-level executive and board director known for her extensive experience in scaling and transforming technology companies. Her career spans diverse environments from startups to Fortune 500 corporations, with a focus on helping leaders navigate digital transformation and global expansion. Yvonne currently serves on the boards of Arista Networks, Forrester Research, JFrog, Rubrik, Braze, Infoblox, and Alation, as well as the Easton Technology Management Center at UCLA. She also serves as a senior advisor to the Ontario Teachers' Pension Plan and Lightspeed Venture Partners. 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/

In this episode of Aon at the Top, I sit down with Helen Riley, COO and CFO at Google X (the moonshot factory), to explore her unconventional journey from studying philosophy at Oxford to leading one of the world's most ambitious innovation engines. We dive into how disciplined financial rigor enables radical experimentation, why most moonshots fail (and why that's the point), and the leadership lessons she learned from terrible feedback early in her Google career.

In this episode of Aon at the Top, host Nicole Ward sits down with Elias Nader to dig into what it truly means to lead from a place of purpose, resilience, and vision.

In this episode of Aon at the Top, I sit down with Dana Hollinger, board member at Apollo Private Markets and former CalPERS trustee, to explore her remarkable journey from working in her father's optometry practice to overseeing $500+ billion in pension assets. We dive into the early experiences that shaped her leadership philosophy, the mentorship that transformed her thinking about value creation, and how she navigated the complex world of institutional governance and risk management.