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

Etsy’s Former CTO: Don’t Reject an Opportunity Before It Exists. | Rachana Kumar

Thu, 05 Mar 2026 17:50:09 GMT

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 home

00:14:33 - The 2017 Etsy turnaround

00:19:18 - Building Etsy's culture of innovation

00:27:09 - Balancing data-driven decisions with intuition while staying connected to 1,200+ people

00:34:01 - Leading responsible AI at Etsy

00:42:14 - The best career advice she ever received

00:47:25 - How to lead through uncertainty

00:56:14 - 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/

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Leading Through Change: Lessons from the Boardroom and the CEO Seat | Caroline Tsay

Tue, 17 Feb 2026 15:00:00 GMT

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.

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CLO Says Why Moving Fast Without All the Answers Is Required in Executive Roles | Yasmin Saeed Coffey

Tue, 20 Jan 2026 15:00:00 GMT

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.

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Chief Legal Officer: The Mistake That Breaks Startups | Derrick Alesevich

Tue, 23 Dec 2025 17:00:00 GMT

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.

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Speaking Truth: A Chief Legal Officer's Guide to Bold Leadership with Shanti Ariker

Thu, 04 Dec 2025 13:29:21 GMT

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.

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From Tragedy to Triumph: Scaling Companies and Leading Boards with Yvonne Wassenaar

Tue, 11 Nov 2025 08:42:46 GMT

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 risk

4:36 - You get promoted because you make people above you successful

8:03 - Being pushed to get startup experience before 50

9:51 - The ski jump analogy

12:33 - Resilience is fighting through hard times for something that matters

19:23 - None of us really know what we're capable of until the time calls upon us

25:02 - During uncertainty, we make the hardest decisions

27:43 - Leading through chaos

30:05 - The rise of independent directors in private companies

32:02 - The difference between being an operator vs. a strategic advisor on boards

40:41 - Separate your emotion from someone's intentionality to get further in life

43:00 - Making hard CEO decisions: when to break teams out to innovate faster

58:22 - The power of many small decisions

Connect 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/

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Inside the Moonshot Factory: Leadership Lessons from Google X COO Helen Riley

Fri, 24 Oct 2025 11:02:06 GMT

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.

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Elias Nader: Leading with Intention at the Top

Fri, 17 Oct 2025 09:00:00 GMT

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.

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A Woman's Path to Institutional Leadership with Dana Hollinger

Wed, 10 Sep 2025 13:00:33 GMT

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.

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Leading with Empathy, Data and Purpose: A Conversation with Carolyn Herzog

Wed, 27 Aug 2025 10:00:00 GMT

Carolyn Herzog joins us on AON at the Top to explore her inspiring journey—from leading nonprofit initiatives to redefining business impact through data-driven strategies and inclusive leadership. In this episode, Carolyn shares how she harnessed analytics to transform organizational culture, scale social impact, and unify diverse teams around bold missions. Along the way, we dive into her “three pillars” of sustainable leadership, practical tips for emerging leaders, and the role empathy plays in driving innovation. Whether you’re a corporate executive, founder, or changemaker, Carolyn’s insights will leave you motivated to lead with integrity and purpose.

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Dave Chun: From Immigrant to CEO

Wed, 13 Aug 2025 13:00:00 GMT

In this episode of Aon at the Top, I sit down with Dave Chun, co-founder and CEO of Equilar, to explore his remarkable journey from Korean immigrant to pioneering entrepreneur in executive intelligence. We dive into how early experiences with discrimination built his resilience, the story behind founding Equilar during the dot-com crash, and his company's evolution from SEC data mining to becoming the trusted source for Fortune 500 executive compensation and governance insights. Dave shares candid lessons about entrepreneurial grit, the importance of CEO peer networks, and how Equilar's latest AI innovations are revolutionizing corporate governance research.

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From Counsel to C-Suite: Arthi Chakravarthy on Leading with Integrity and Impact

Fri, 01 Aug 2025 20:45:45 GMT

In this episode of Aon at the Top, I sit down with Arthi Chakravarthy, EVP, Chief Legal Officer & Corporate Secretary at Enovix, to explore her unique journey from private practice to the executive suite. Arthi shares the pivotal moments that shaped her career, what it means to lead with authenticity and courage in high-stakes environments, and how her background in law informs her approach to business and governance today. We also dive into the evolving role of corporate legal teams, boardroom dynamics, and her commitment to mentorship and inclusion in the tech space. Whether you’re navigating leadership in a regulated industry or forging your own path to the C-suite, Arthi’s insights are a masterclass in purpose-driven leadership.

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Doing Good & Doing Well | Laurel Mintz

Tue, 22 Jul 2025 17:59:00 GMT

In this episode of Aon at the Top, Nicole Ward sits down with powerhouse CEO and venture capitalist Laurel Mintz, founder of Elevate My Brand and General Partner at Fabric VC. Together, they explore her unconventional journey from aspiring lawyer to agency founder, the pivotal moment when she had to completely rebuild her team culture, and her transition into venture capital. From navigating the challenges of entrepreneurship to her mission of reallocating capital to diverse founders, Laurel shares candid insights on leadership evolution, the importance of transparent money conversations, and why she believes this is the venture vintage to end all vintages.

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From Fired to Fortune | Brenda Morris

Wed, 09 Jul 2025 15:58:00 GMT

In this episode of Aon at the Top, Nicole Ward sits down with powerhouse CFO and board member Brenda Morris, a dynamic finance executive with over 35 years of experience across retail, wellness, manufacturing, and technology. Currently serving on the boards of Boot Barn, Xponential Fitness, and iHerb, Brenda shares her unconventional journey from aspiring flight attendant to C-suite executive. Together, they explore the pivotal moments that shaped her career, her philosophy of turning setbacks into stepping stones, and why she believes getting fired long ago was the best thing that ever happened to her. From enterprise risk management to building positive energy in the boardroom, Brenda offers practical wisdom on values-based leadership and why success equals happiness.

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Shannon Nash: Scaling Innovation, Shaping Culture, and Owning the C-Suite

Tue, 27 May 2025 09:00:00 GMT

In this episode of Aon at the Top, Nicole Ward sits down with powerhouse CFO, board member, and transformational leader Shannon Nash. As the CFO of Wing (an Alphabet company), Shannon brings a unique blend of financial acumen, legal expertise, and bold leadership to the table. Together, they explore her unconventional path to the C-suite, the lessons she's learned from scaling innovation, and how she cultivates cultures of excellence in high-growth environments. From navigating corporate governance to championing DEI and digital transformation, Shannon shares insights that are both inspiring and practical for executives at every stage of their journey. Tune in for a candid conversation about taking smart risks, building influence, and leading with purpose at the intersection of finance, technology, and impact.

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Interview with Corporate Trailblazer and Turn Around CEO, Chelsea Grayson

Wed, 07 May 2025 09:00:00 GMT

In this episode of Aon at the Top, Nicole Wad sits down with powerhouse CEO and board director, Chelsea Grayson-Known for leading iconic turnarounds at American Apparel, True Religion, and Delta Dental, and for her bold presence in the boardroom. Chelsea opens up about the leadership decisions that defined her journey, how she built her career on conviction and courage, and what it really takes to lead companies through high-stakes transformation. From navigating brand reinvention to making fearless boardroom moves, this episode is packed with insight for anyone who wants to lead with impact and resilience.

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Senior Executive And Board Member Lauren Silvernail On Humble Beginnings And Doing The Right Thing When No One Is Looking

Fri, 11 Apr 2025 09:00:00 GMT

In this episode of Aon at The Top, host Nicole Ward engages with Lauren Silvernail, a distinguished senior executive and public company board member in the life sciences sector. Lauren delves into her inspiring journey from modest beginnings to ascending the ranks of leadership in renowned public life science companies. She emphasizes the pivotal role of integrity, encapsulating the philosophy of "doing the right thing when no one is looking."

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How Leaders Balance Vision and Opportunism: A Conversation with Public Company Board Member and Executive, Kim Vogel

Fri, 28 Mar 2025 09:00:00 GMT

This week, I had the honor of sitting down with Kim Vogel-CFO, public company board member, fintech entrepreneur, and one of the most influential women in business.Kim’s story is a powerful example of what’s possible when you balance long-term vision with the courage to seize unexpected opportunities.We talked about: ✅ Navigating career pivots (including a layoff that led to Harvard Business School)✅ Building and exiting M Foundry, a pioneer in mobile banking✅ Leading with ethics, resilience, and clarity in high-stakes moments✅ Teaching, board leadership, and empowering women in tech and financeHer journey is full of practical wisdom for anyone navigating growth, risk, and leadership at the highest levels.💡 One of my favorite takeaways: “Sometimes the best decisions aren’t part of a plan—they’re part of the process.”🎧 Tune in to this episode of AON at the Top and hear how Kim has turned challenge into impact across every chapter of her career.

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From Healthcare Executive to Boardroom Leader: Dr. Jackie Kosecoff on Strategy, Resilience & Career Growth

Fri, 07 Mar 2025 18:45:00 GMT

Welcome to AON at the Top with host Nicole Ward, Senior Vice President of Sales at AON. On the podcast, we interview distinguished executives, C-suite and board members about their journeys and paths to success with the mission to help businesses make better decisions by transforming risk into resilience. On today's episode, Nicole is joined by Dr. Jackie Kosekoff, a highly experienced executive and board member in health services and technology. Dr. Kosekoff reflects on her career choices, emphasizing her desire to make a difference in healthcare and her passion for building organizations. Dr. Kosekoff provides advice for professionals aspiring to executive or board roles, stressing the importance of truly understanding the responsibilities associated with leadership positions.

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