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Jai Shekhawat is a Partner at Chicago Ventures and a highly successful entrepreneur, best known as the founder and former CEO of Fieldglass, which was acquired by SAP. He is an experienced investor and advisor to early-stage technology and healthcare companies.
Jai Shekhawat primarily invests in early-stage companies within the technology and healthcare sectors. His focus areas include enterprise software, Software-as-a-Service (SaaS) solutions, and disruptive healthcare technology, particularly B2B innovations.
Jai Shekhawat works as a Partner at Chicago Ventures, a leading venture capital firm based in Chicago, Illinois. He contributes to the firm's investment strategy and supports its portfolio companies.
Jai Shekhawat is a Partner at Chicago Ventures based in Chicago, Illinois. He previously founded and served as the Chief Executive Officer of Fieldglass, a cloud-based vendor management software company that he scaled to a $1 billion acquisition by SAP in 2014. Before his entrepreneurial ventures, he worked as a strategy consultant at McKinsey & Company and held senior executive roles at Syntel. He holds a Master of Business Administration from the Kellogg School of Management at Northwestern University and a Bachelor of Science in management science from BITS Pilani. In addition to his venture capital work, he serves on the boards of several organizations, including FourKites, the Field Museum, and the Chicago technology hub 1871. His current focus centers on advising and investing in early-stage enterprise software and business-to-business technology startups across the Midwest.
Jai Shekhawat stands as a prominent figure in the venture capital landscape, serving as a Partner at Chicago Ventures. In this pivotal role, he brings a wealth of experience and a founder-first mentality to the firm's investment decisions, actively seeking out and nurturing the next generation of innovative companies. His work at Chicago Ventures is characterized by a deep commitment to identifying early-stage technology and healthcare startups with high growth potential.
Shekhawat's investment focus areas are largely shaped by his impressive career background. He is particularly interested in enterprise software, Software-as-a-Service (SaaS) solutions, and disruptive healthcare technology. His keen eye for B2B innovation stems from his own entrepreneurial journey, allowing him to truly understand the challenges and opportunities faced by founders in these complex sectors. He seeks out companies that demonstrate strong product-market fit, scalable business models, and visionary leadership.
Before joining Chicago Ventures, Jai Shekhawat made a significant mark as the founder and CEO of Fieldglass, a leading cloud-based vendor management system. Under his leadership, Fieldglass grew into a global powerhouse, ultimately being acquired by SAP in 2014 for a reported billion dollars. This monumental success not only solidified his reputation as a visionary entrepreneur but also provided him with invaluable insights into building, scaling, and exiting a technology company. This firsthand experience is a cornerstone of his approach at Chicago Ventures, where he acts as a strategic advisor and mentor to portfolio companies, helping them navigate growth, market expansion, and operational excellence.
His career prior to Fieldglass also included roles at A.T. Kearney and SAP, further diversifying his expertise across consulting and enterprise software. This diverse background equips him with a comprehensive understanding of various industries and business models, making him a highly effective and sought-after investor. While specific individual investments at Chicago Ventures are part of the firm's collective portfolio, Shekhawat's influence is evident in the firm's strong track record in the enterprise tech and healthcare sectors, reflecting his strategic insights and operational acumen. He is dedicated to fostering innovation and contributing to the vibrant startup ecosystem, particularly within the Midwest and beyond.
