Fundraising Fox

Jai Shekhawat

Investor

Partner at Chicago Ventures · Board director at HighGround Enterprise Solutions

Chicago, Illinois

Writes $100K – $5M checks · typically $1.5M

Find your path to Jai

3,093 people in our graph share verified history with Jai — schools, employers, funds. One of them is your warm intro.

Stephane KurganunlockedJai: together at McKinsey & Company (1997–1998)
×7Jai: together at McKinsey & Company
×3Jai: together at Northwestern University - Kellogg School of Management
Jai: together at Birla Institute of Technology and Science, Pilani

About

Jai Shekhawat is CEO and co-founder of Natural Machine. He has experience in venture fundraising, enterprise software development, management consulting, and sales and marketing.

Board director at HighGround Enterprise Solutions

Intro paths

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In turn, Jai can intro founders to HighGround Enterprise Solutions's investors below.

HighGround Enterprise Solutions's investors · 1

Chicago VenturesChicago · $250K – $1M checks · since 2016

Co-founders at HighGround Enterprise Solutions

VS
Vipon SandhirExecutive Officer, Director
VS
Vip SandhirExecutive Officer, Director

Experience

  1. Natural MachineCEO and Co-Foundercurrent2025 — presentChicago, IL
  2. Madison Dearborn Partners, LLCChairman, Technology Advisory Boardcurrent2014 — presentChicago
  3. A.TeamAdvisorcurrent2021 — presentNew York, New York, United States
  4. FourKites, Inc.Board Membercurrent2017 — presentGreater Chicago Area
  5. SomrusBoard Membercurrent2016 — present
  6. HealthEngine LLCBoard Membercurrent2016 — presentMiami, Florida, United States
  7. BlueCatBoard Member2017 — 2022Toronto, Canada Area
  8. Fleet CompleteBoard Member2015 — 2022Toronto, Canada Area
  9. Utopia Global, Inc.Board Member2015 — 2020Greater Chicago Area
  10. CubiiAdvisor2015 — 2020Chicago, Illinois, United States
  11. Signal ™Board Member2016 — 2020Greater Chicago Area
  12. OfficeLuvBoard Member2014 — 2018Chicago, Illinois, United States
  13. SAP FieldglassFounder and CEO1999 — 2015Chicago, Illinois, United States
  14. Quinnox, Inc.Co-Founder and Member of the Supervisory Board1999 — 2014Chicago, Illinois, United States
  15. McKinsey & CompanyEngagement Manager1996 — 1998
  16. SyntelHead of Business Operations1988 — 1994
  17. Tata Burroughs LimitedSoftware Developer1985 — 1988New Delhi Area, India

Skills & more

Languages English · Hindi

From Jai's professional profile.

Deals · 3

Four KitesBoard seat

via Chicago Ventures · filed Feb 2019 · $50M raise

HighGround Enterprise SolutionsBoard seat

via Chicago Ventures · filed Jan 2018 · $7.5M raise

OfficeLuvBoard seat

via Chicago Ventures · filed Mar 2016 · $4M raise

Attribution from SEC filings, press coverage, and firm rosters.

Colleagues at Chicago Ventures

Emma Lawler
EIR at Chicago Ventures
Eric Duboe
Partner at Chicago Ventures
Ford Johnstone
Associate at Chicago Ventures
Kevin Willer
Venture Partner at Chicago Ventures
Lindsay Knight
Partner at Chicago Ventures
Rob Chesney
Partner at Chicago Ventures
Shawn Park
Associate at Chicago Ventures
Stuart Larkins
Partner at Chicago Ventures

Frequently asked questions

Who is Jai Shekhawat?
Jai Shekhawat is CEO and co-founder of Natural Machine. He has experience in venture fundraising, enterprise software development, management consulting, and sales and marketing.
Where does Jai Shekhawat work?
Jai Shekhawat is Partner at Chicago Ventures and Board director at HighGround Enterprise Solutions.
What check size does Jai Shekhawat write?
Jai Shekhawat typically writes checks of $100K – $5M.
What boards does Jai Shekhawat sit on?
Jai Shekhawat holds tracked board seats at Four Kites, HighGround Enterprise Solutions, OfficeLuv.
Where did Jai Shekhawat go to school?
Jai Shekhawat studied at Northwestern University - Kellogg School of Management (MBA, Strategy); Birla Institute of Technology and Science, Pilani (MMS, Management); Delhi Public School Mathura Road (High School).

Same school

Also attended Northwestern University - Kellogg School of Management842

Jenny LeeSenior Managing Partner at Granite AsiaKunal BahlCo-founder of Snapdeal; co-founder of Titan CapitalCristina JunqueiraCo-founder of NubankAndy FligelSenior Managing Director at Intel CapitalDavid Clark GuillermoInvestments at Impact America FundGiuseppe DonvitoPartner at P101 Ventures

+ 836 more

Also attended Birla Institute of Technology and Science, Pilani234

SomnathTechnology Partner and Chief Data Scientist at Clear VenturesSanjot MalhiPartner at NorthzoneRishabh KaulVenture Partner at Hoxton VenturesAnirvan ChowdhuryDirector at Qualcomm VenturesSanjeev KumarVenture Partner at FusionYash SankrityayanManaging Partner, Southeast Asia at Jungle Ventures

+ 228 more

Also attended Delhi Public School Mathura Road10

Ashish TanejaFounding Partner & CEO at growX VenturesDhruv KapoorPartner at Anicut CapitalSonal VarmaGlobal Director - Live Initiatives at NODWIN GamingAnupam BehuraPartner at Bain Capital VenturePrabhakar JainChief Strategy and Business Development Officer - Pioneering Businesses at Pidilite Industries LimitedUdit AhujaVenture Partner at DST Global

+ 4 more

Shared employers

Also worked at Fleet Complete3

Matthew M. DenisonInvestor at Madison Dearborn PartnersAlex S. FisherInvestor at Madison Dearborn PartnersMohit TalwarPartner, Investments at Maverix Private Equity

Also worked at Utopia Global, Inc.2

Liron GitigVenture Partner at Overture ClimateAndy MartinStartup Mentor at Primordial Ventures

Also worked at McKinsey & Company2,000

Elad GilSolo general partner investing through Gil CapitalAnn Miura-KoCo-founding Partner at FloodgateJeremy LiewPartner at Lightspeed Venture PartnersMike SpeiserManaging Director at Sutter Hill VenturesJeremy LevinePartner at Bessemer Venture PartnersFabrice GrindaCo-founder & Managing Partner at FJ Labs

+ 1,994 more