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Jai Shekhawat

Investor

Board director at OfficeLuv · Board director at HighGround Enterprise Solutions

Chicago, Illinois

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

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You →Mary · together at Madison Dearborn Partners, LLC (2014–2020) →Jai

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You →Jamie · together at Madison Dearborn Partners, LLC →Jai

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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 OfficeLuv

Intro paths

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In turn, Jai can intro founders to OfficeLuv's investors below.

OfficeLuv's investors · 5

500 GlobalPalo Alto · $150K checks · since 2015Chicago VenturesChicago · $250K – $1M checks · since 2016Hyde Park AngelsChicagoKDWC VentureChicago · since 2019Method CapitalChicago · $1M – $10M checks

Co-founders at OfficeLuv

KM
Kathryn MaddenExecutive Officer, Director, Promoter
CHChris Hartman
Chris Hartman

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.

Other disclosed investments

Sources: SEC Form D filings · curated public sources.

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 Board director at OfficeLuv 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.
What companies has Jai Shekhawat invested in?
Investments tracked here include Built In, Cartavi, Cubii, ForeverCar, Gearflow, Loconav, Minutebox, New Era ADR, Retrofit, Rise Gardens, Semantify, Upshow, and 1 more.
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

Shared employers