561: Bridging Planning and Execution: The Next Frontier of Supply Chain Orchestration, with Cleo
Mahesh Rajasekharan is the President and CEO of Cleo, with a background that includes a PhD in Industrial Engineering and leadership roles at I2 Technologies and Sum Total Systems. He describes his transformation of Cleo as building a "neo-startup," creating a new software category on an established foundation. Rajasekharan argues that true supply chain advancement comes from orchestration—moving beyond visibility to create "systems of action" that bridge planning and execution. He emphasizes that for AI to deliver value, the focus must be on data context and governance. His experience on multiple software boards (Cleo, Ascend Software, Banyan Software) informs his strategy, reinforcing his belief that supply chains must evolve into primary drivers of revenue and business growth.
Today I’m joined by Cleo, the global leader in supply chain orchestration.
Through its innovative Cleo Integration Cloud platform (CIC) and SCO capabilities, Cleo enables the digital ecosystems of thousands of customers and partners by providing highly flexible, industry-focused solutions that bridge the gap between supply chain planning and execution to deliver better real-time decision-making, critical in today’s constantly changing business environment.
Today Mahesh Rajasekharan, President and CEO at Cleo, joins me to talk all about Cleo and what they do; the evolution of supply chain orchestration as the next frontier beyond integration; the findings from Cleo’s brand-new Global Supply Chain Executive Report; and why the real barrier to AI-powered decision-making isn’t the AI, it’s the data underneath it.
Guest bio:
Mahesh Rajasekharan is President and CEO of Cleo, the global leader in supply chain orchestration (SCO) solutions. Mahesh has extensive leadership experience in business, including sales and marketing, operations, and business strategy; in technology, including supply chain management, SaaS, and enterprise software and consulting services; and in finance, including proven acumen around private equity investment, acquisition integration, and P&L management. Since 2012 he has been leading Cleo’s evolution and expansion from a “neo-startup” with a small number of investors to a high-growth, scaled cloud software business, with a strategic growth investment backed by H.I.G. Capital. Prior to leading Cleo, he served as Chief Operating Officer at SumTotal Systems, where he led the dramatic turnaround of this $100 million multinational software company. Previously, he led the High-tech Industry Sector at i2 Technologies, where he managed global sales and a $60 million P&L.
Today Mahesh serves on the Board of Directors for Cleo, Ascend Software, and Banyan Software, and is on the Advisory Board for StartupWind, a social ideation network. He holds a Ph.D. in Industrial Engineering from Texas A&M University, an M.S. in Industrial Engineering from Texas Tech University, and a B.E. in Mechanical Engineering from Anna University, India. He also earned an MBA in Finance, Strategy, and Marketing from the Haas School of Business at UC Berkeley, where he graduated No. 1 in his class. In 2022 he was named an EY “Entrepreneur of the Year” winner in the U.S. Midwest region.
What excites Mahesh about transformation, why he calls Cleo a ‘neo-startup’, and how he has shaped their mission and growth strategy.
Who Cleo is, what they do, and what it means to orchestrate a supply chain, as opposed to simply integrating it.
The problem with historic working siloes, and how orchestration forces collaboration and a customer-first approach.
Cleo’s north star – ‘to make global supply chains better’ – and the big turning points that have defined their evolution.
The ideal client for Cleo, how that profile has changed over the course of their evolution, and why supply chain has to become a revenue driver.
Why Cleo conducts an annual Global Supply Chain Executive Report, and the most surprising findings from 2026.
With 88% of organizations increasing their use of automation, yet 55% reporting increased operational complexity as a result, a closer look at exactly what’s driving that disconnect.
Why only 16% of organizations say they have true end-to-end, real-time visibility across their supply chain, despite visibility being a critical goal for over a decade.
As leaders become increasingly comfortable with AI-based recommendations but still struggle to trust the underlying data, where companies should actually focus if they want AI to deliver real value.
How organizations can improve their data context and trust more quickly.
How companies can streamline order processing with Cleo to course correct problems, improve on-time and in-full performance, boost speed, reduce cost, and enhance customer relationships.
How sitting on the boards of Cleo, Ascend Software, and Banyan Software helps Mahesh understand the wider market and develop Cleo’s own strategy moving forward. “It really makes you understand how universally challenging operational complexity has become… And it provides a strong perspective on what separates companies that successfully transform from those that struggle.”
