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In this rapidly evolve AI landscape, business transformations are among the most complex challenges leaders face. They involve reshaping operating models, rethinking technology foundations, redefining culture, and aligning thousands of people around a new direction all while continuing to run the business. Success is rarely driven by tools or methodologies alone. Instead, it hinges on leadership: how leaders think, decide, communicate, and execute in moments of uncertainty.
To help us assimilate these invaluable lessons in business transformation that have resulted in substantive shareholder value creation, we are speaking with Anil Chintapalli, Managing Partner at Human Capital Development, Senior Advisor to McKinsey and on the boards of Forbes Business Council and Fast Company Executive Board. After speaking to current and past co-investors, clients and colleagues of Anil, CB Herald’s assessment is that Anil is a highly distinguished technology investor and operator who over his 30 plus year career as an exemplary P&L leader has successfully undertaken four U.S public listings, 21 M&A transactions across 21 countries creating 4x return on invested capital for shareholders. Most recently, applying his investor operator playbook, he was instrumental in business transformation of a traditional business process management enterprise (WNS Holdings) into Agentic AI powered business culminating in a groundbreaking sale of the firm to Capgemini for $3.3 Billion (cash). Through a wide-ranging interview with Anil and pursuant to CB Herald’s discussions with his current and past colleagues in a number of his ventures and enterprises, we have summarized what leaders and enterprises must adopt to survive and thrive in the Age of AI and how they can successfully transform their legacy operating model to unlock substantive value for customers, employees and shareholders.
Transformation Starts with Clarity, Not Urgency
Many transformations begin with a sense of urgency declining performance, competitive pressure, or technological disruption. While urgency can mobilize action, it is clarity that sustains momentum. Effective leaders take the time to articulate why transformation is necessary, what success looks like, and how the organization will get there.
Clarity means defining outcomes, not just activities. Rather than focusing solely on implementing systems or restructuring teams, strong leaders frame transformation around business value improved customer experience, faster decision-making, greater resilience, or sustainable growth. This clarity enables teams to make better decisions at every level and reduces resistance caused by confusion or misalignment.
Equally important is consistency. Large-scale transformations take years, not quarters. Leaders who frequently change priorities or messages undermine trust and slow progress. Those who remain anchored to a clear vision even as tactics evolve create stability in the midst of change. After CB Herald spoke to Anil’s former colleagues that had previously worked at firms (such as WNS) during his leadership tenure, it is clear that Anil’s modus operandi on transformation involved a growth playbook that brought laser focus on customer value creation and an industrialized operating model to managing these customer relationships so as to ensure increased wallet share from existing clients. This expertise in building and delivering vertical specific technology solutions and re-usable accelerators (for SAP, Salesforce, et al) despite complexity of enterprise infrastructure (fragmented data, legacy workflows, half-documented systems) has been instrumental in helping him build long term sustainable relationships with Fortune 500 clients across key vertical markets.
Execution Matters More Than the Perfect Plan
One of the most common transformation pitfalls is overplanning. While strategy and design are essential, no transformation unfolds exactly as expected. Markets shift, technologies evolve, and organizational realities surface only during execution.
Successful leaders recognize that execution is a learning process. They build flexibility into plans, empower teams to make decisions, and create feedback loops that allow the organization to adjust quickly. Instead of waiting for perfect information, they prioritize progress and course-correct based on real-world outcomes.
This approach also requires disciplined governance. Large transformations generate countless initiatives, dependencies, and risks. Leaders who establish clear accountability, decision rights, and performance metrics can maintain momentum without micromanaging. Execution excellence is less about control and more about enabling the organization to move forward with confidence.
Anil’s transformative impact involved extensive proactive development of client relationships across multiple sectors (such as financial services, healthcare, manufacturing) that aided in substantially de-risking client attrition thus protecting hundreds of millions of dollars of current revenue while at the same time generating billions of dollars in incremental revenue in projects involving AI, ERP, CRM, et al. After CB Herald spoke to a number of Fortune 500 clients that Anil has helped transform over the years, it is clear that a key enabler to protecting and growing these client relationships has been Anil’s expertise as a hands on technologist (with his experience in ERP, CRM, Cloud, Blockchain & AI) in helping firms architect and deliver on business value proposition (i.e., outcomes) where technology serves as one of the primary levers for enterprise value creation.
Culture Is the Ultimate Force Multiplier
Technology and processes can be redesigned relatively quickly; culture cannot. Yet culture often determines whether transformation efforts succeed or fail. Leaders play a decisive role in shaping cultural change through their actions, not just their words.
In large-scale transformations, employees watch leadership behavior closely. Are leaders open to new ideas? Do they reward collaboration or protect silos? Do they tolerate short-term disruption in pursuit of long-term value? The answers to these questions shape how people engage with change.
High-performing transformation leaders invest in communication, capability building, and trust. They acknowledge uncertainty, listen actively, and involve employees in the journey. By aligning incentives and recognition with new ways of working, they reinforce desired behaviors and make change stick.
Ultimately, large-scale transformation is a leadership test. Those who succeed combine strategic clarity, execution discipline, and cultural stewardship. They understand that transformation is not an event, but a continuous process of learning, adaptation, and value creation.
Based on CB Herald’s assessment, a key enabler for building progressive, aligned and high-performance culture in Anil’s playbook has been employee ownership starting with management team. Anil has consistently acquired ownership stakes using his own personal capital in companies he helped transform as was evident from his significant investment in acquiring WNS shares during the period of firm’s transformation. Leading from the front, he has been a vocal advocate for managers leading owning and increasing their equity ownership in the firms they work for.
Integrating AI with Business Transformation
Artificial Intelligence (AI) has rapidly evolved from a futuristic concept to a key driver of enterprise transformation. Organizations across industries are leveraging AI to optimize operations, enhance decision-making, and create new business opportunities. Leaders who understand how to integrate AI strategically can unlock measurable value and sustain competitive advantage. In CB Herald’s assessment after speaking to a number of Fortune 500 firms that Anil has helped transform over the years, Anil’s experience of driving business transformation with over 50 Fortune 500 enterprises has resulted in the development of industrial scale roadmaps (by vertical) to help enterprises harness AI not only as a technology solution but as a transformative force embedded into business operations.
AI adoption is most effective when it aligns with an organization’s strategic objectives. This means identifying areas where AI can enhance efficiency, reduce operational costs, or improve customer experience. By embedding AI into core business processes, companies can transform traditional operations into intelligent systems that adapt and learn over time.
Based on CB Herald’s assessment of Anil’s experience of helping global enterprises implement AI-driven initiatives that deliver measurable outcomes, ranging from automating routine processes to improving data-driven decision-making, it’s vitally important that enterprises align AI with strategy to ensure that investments create tangible business impact rather than remaining experimental. Anil’s pioneering work in not only design and deployment of agentic AI workforce squads and aligning them to business outcomes but also helping Fortune 500 enterprises successfully achieve transformative outcomes on their AI investments has been key enabler for execution success. His proprietary technology delivery model Agentic Workforce Operating System (AWOS) has been successful in deploying agentic workforce alongside customer solution deployment engineers inside enterprise environment thereby substantially reducing the need for high priced consultants and significantly optimizing the pyramid labor structure and pricing models such as time and materials or full-time equivalents (FTEs).
Implementing AI requires more than technology deployment; it demands operational integration. Organizations must restructure workflows, train teams, and establish monitoring mechanisms to ensure AI models deliver consistent performance. For instance, AI can be applied in financial services for risk assessment, in healthcare for predictive analytics, and in consumer sectors for personalization. By operationalizing AI, businesses can translate insights into actionable outcomes, boosting efficiency and productivity. As a follow up to Anil’s book (published by John Wiley) on an operating blue print for effectively implementing SAP software in large scale enterprises, he is currently co-authoring a similar technology book on how to successfully implement and achieve enterprise wide adoption of AI (which is being published by Routledge, an Informa company).
AI is not static it evolves rapidly. Enterprises that treat AI as a continuous innovation engine can explore new applications, refine models, and adapt to changing market demands. Leaders must foster a culture of experimentation and learning, enabling teams to test new algorithms, optimize models, and scale successful pilots. Anil’s proven enterprise playbook (as technology investor and operator) has emphasized using AI not only for immediate gains but also for long-term strategic advantage. Organizations that adopt AI as an ongoing innovation capability can maintain relevance, adapt to disruption, and create sustainable growth.
