JAI SHEKHAWAT
Partner at Chicago Ventures
About
Jai Shekhawat is a distinguished Partner at Chicago Ventures, where he leverages his extensive entrepreneurial background to identify and support promising early-stage companies. He primarily focuses on investments in the healthcare technology, software, and enterprise SaaS sectors, guiding founders through critical growth phases. His unique perspective as a successful founder deeply informs his investment strategy.
Experience
Deep Dive
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.
Frequently Asked Questions
Who is Jai Shekhawat?
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.
What does Jai Shekhawat invest in?
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.
Where does Jai Shekhawat work?
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.