Why 85 Percent of New CEOs Are First Timers, with Anand Eswaran
What actually makes a leader fit a job, when the written job spec says one thing and the company needs another? That is the question at the center of my conversation with Anand Eswaran, CEO of Veeam Software, a 15 billion dollar company that exists to put data back together after ransomware attacks, outages, and some of the worst days a company ever has.
Anand is a first time CEO who will tell you, bluntly, that he did not match the spec the board wrote for his own job. The posting called for a proven CEO with a product engineering pedigree and an industry veteran as backup. He was none of the three. We talk about why the board hired him anyway, and why that story connects to a much bigger pattern in executive fit and hiring a CEO: the research shows roughly 85 percent of newly appointed S&P 1500 CEOs are first timers, and there is very little statistical difference in performance between first time and repeat CEOs once you control for the momentum they inherit.
We trace Anand's path from a childhood in Mumbai taking apart radios and the family's first computer, through grad school in Missouri, into a career that moved through consulting, services, sales, Microsoft Digital, running Microsoft's enterprise business, serving as COO of RingCentral, and finally to Veeam. He describes it as a series of nonlinear steps rather than a planned climb, and explains why that range matters more than a straight line when a board is thinking about leadership fit.
We also get into what changed for him operationally once he became CEO: learning to delegate without abdicating, rewiring his relationship with speed, and what he calls firing the operator inside himself. He talks about culture as a concrete operating discipline rather than a soft idea, how services experience shapes retention and expansion in a SaaS business, and how he is using AI inside Veeam, from a bot paired with every seller to the deeper question of trusting the data a model is trained on.
This is a conversation about how leadership coaching programs and boards alike should be thinking past the resume, toward the underlying qualities that actually predict whether someone can do the job in front of them.
Key takeaways:
- Veeam's CEO spec called for a proven CEO with a product and engineering background. Anand had none of those three things, and was hired anyway because of how he leads, not his resume.
- Roughly 85 percent of newly appointed S&P 1500 CEOs are first time CEOs, and there is little statistical performance difference between first timers and repeat CEOs once you control for inherited momentum.
- A CEO accounts for an estimated 15 to 30 percent of firm performance, a smaller share at large companies and a larger share at small ones.
- Anand's biggest personal shift moving from Microsoft to Veeam was learning to delegate without abdicating and slowing his own bias for speed.
- Culture, in his view, is a specific operating discipline (zooming in and out, grounding decisions in data, building a system bigger than any one person) not a soft perk.
- Retention and expansion, not new customer acquisition, are now the real growth engine in software, and a services background builds exactly that muscle.
- AI's biggest impact is not making individual tasks faster, it is forcing companies to reimagine entire workflows, which is how Veeam cut its CAC payback from 30 months to roughly 12.
- The hardest unresolved question in AI right now is whether you can trust the data a model is trained on, which is the problem Veeam is built to solve.
Connect with Jason: https://www.linkedin.com/in/jasonbaumgarten/
Email the show here: jason@fithappens.fm
Email the show here: jason@fithappens.fm
FitHappens is hosted by Jason Baumgarten, Former Head of the Global CEO and Board Practice at Spencer Stuart. The show covers CEO succession, hiring a CEO, board of directors dynamics and governance and leadership fit and performance. New episodes every week at fithappens.fm.
Connect with Jason: https://www.linkedin.com/in/jasonbaumgarten/
Email the show here: jason@fithappens.fm
Email the show here: jason@fithappens.fm
Timestamps
00:00 A kid in Mumbai taking apart radios
01:01 Welcome Anand Eswaran to Fit Happens
03:14 His first computer and Prince of Persia
05:36 Moving from Mumbai to Missouri
09:52 Was there a wrong turn in his career
13:13 The Veeam CEO spec he did not match
15:56 85 percent of new CEOs are first timers
20:26 Why Veeam's success is a system not one person
22:16 Firing the operator inside himself
25:29 What a services background taught him
29:05 How AI is changing his leadership
33:50 Can you trust the data a model learns from
00:00 A kid in Mumbai taking apart radios
01:01 Welcome Anand Eswaran to Fit Happens
03:14 His first computer and Prince of Persia
05:36 Moving from Mumbai to Missouri
09:52 Was there a wrong turn in his career
13:13 The Veeam CEO spec he did not match
15:56 85 percent of new CEOs are first timers
20:26 Why Veeam's success is a system not one person
22:16 Firing the operator inside himself
25:29 What a services background taught him
29:05 How AI is changing his leadership
33:50 Can you trust the data a model learns from
