My guest today is Mahesh Rajasekharan, CEO of Cleo, a software platform for supply chain system integrations. A few months ago I asked a few friends which sales-focused CEO they admired most and they all unanimously said Mahesh. With Mahesh at the helm, Cleo has grown from a single-digit ARR business in 2012 to nearly $100 million in ARR today, with even greater ambitions for the future. He has built some of the most robust and high-performing sales and product teams I’ve seen and is a value-adding investor and advisor to many other CEOs.

Mahesh and I talk about the story of Cleo and how they drive customer value, pivot points along the growth journey, building best-in-class sales and product orgs, growth while remaining profitable, private equity ownership, and so much more. Please enjoy this fantastic conversation with Mahesh Rajasekharan.

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Links:

Cleo

Mahesh on LinkedIn

Topics:

(00:04:06) Cleo and how Mahesh has evolved the business

(00:11:37) Identifying customer needs

(00:14:04) Growing and coordinating a product team

(00:18:17) Communicating with customers

(00:21:20) Building and scaling a Sales organization

(00:37:15) How the CEO role has changed

(00:39:02)Self-evaluation

(00:42:49) Defining profitable growth

(00:48:56) Themes for companies who can’t become profitable

(00:52:17) An example of a project that wasn’t working initially but learned it would down the road

(00:54:13) Experiences as a private equity-backed CEO

(00:58:21) The most enjoyable part of the CEO role

(00:59:27) M&A

(01:03:47) Advice for software CEOs in scaling