Sai Kumar

About Me

I'm a joint MBA/MS student at the University of Chicago, former Space Force engineer, and former Army pilot.

Education

University of Chicago

MBA & MS Computer Science (Joint Degree)Sep 2024 – Jun 2026

MBA Concentration in Entrepreneurship; MPCS Coursework in Python, Networks, and Databases

United States Military Academy

BS Systems Engineering with HonorsJul 2014 – May 2018

Dean's List eight semesters; Published three international papers; Powerlifting Team

Professional Experience

Investment Analyst

Listen VenturesChicago, ILOct 2024 – Present

Sourced, analyzed, and presented recommendations for over 30 startup investments ranging from pre-seed through Series A. Conducted market research and created investment thesis reports on consumer AI.

30+ startup investments analyzedConsumer AI investment thesisLP coordination and fund management
Operations Intern (Skillbridge)

FlashCashOrlando, FLApr 2024 – Sep 2024

Rewrote existing React/NextJS website as iOS app in Swift using AI tools. Oversaw customer acquisition generating over $100k in annual revenue streams.

React to Swift conversion$100k+ revenue generationData analytics scaling
Lead Engineer, EWS Operational Capabilities

United States Space ForceLos Angeles, CASep 2022 – Sep 2024

Led engineering team developing next-generation weather satellites, delivering global operational capabilities to millions of users.

3M+ global users servedNext-gen satellite developmentDoD acquisition innovation
Aviation Officer

United States ArmySavannah, GA & RomaniaMay 2018 – Sep 2022

UH-60M Blackhawk Pilot-In-Command and Air Mission Commander. Managed $6M+ flying hour program and led 64 soldiers in deployed environment.

Pilot-In-Command qualification$6M+ program managementNATO operations in Europe

Skills & Expertise

Investment AnalysisStartup EvaluationPythonSwiftReact/NextJSMilitary LeadershipAviationReal Estate InvestmentMarket ResearchSystems EngineeringProject Management

Languages

HindiAdvanced Intermediate
SpanishAdvanced Intermediate
TeluguElementary (Verbal)

Additional Information

Investments & Achievements

• Real Estate Investor

• 2021 #1 New Airbnb Host in Georgia

• Angel Investing in consumer and biotech

Certifications & Interests

• FAA Commercial Fixed & Rotary Wing w/Instruments

• Advanced Open Water Scuba Diving

• Machine Learning & AI Research