Jiya S.
Studied at Washington University in St. Louis
Works at Outsiders Fund
Available December 4 at 3:30 PM UTC
Please message for additional availability outside of my standard hours! I can be very flexible on weekends.
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About Jiya
I’m a venture investor at Outsiders Fund in New York, where I invest in early-stage software (seed & series A). Getting here wasn’t linear. I started my career in Citi’s startup-focused innovation group, and also spent time working with early-stage founders as a consultant and advisor. I ran my own small business in college, helped build product inside a large company, and eventually used that experience to break into venture -- without banking, without the “traditional” feeder background, and without an obvious path in. Along the way, I learned how to position myself, tell my story effectively, build real founder relationships, and identify where I could add value despite not fitting the typical mold. That process shaped how I help people navigate their own careers.
Why do I coach?
I coach because I know exactly how hard it is to break into VC when you are not coming from a preset track. I had to figure out what skills actually mattered, how to frame my experience, how to stand out in founder and partner conversations, and how to navigate an interview process and industry that is notoriously opaque. When I was trying to break in, Leland was one of the few resources that genuinely helped me, both in understanding how to position myself and in demystifying the industry enough to approach the process with confidence instead of guesswork. That experience made the difference for me, and it is a big part of why I coach now. I want to make the path clearer for people who are trying to get into venture, transition into tech, or simply figure out what career direction fits them. I learned through a lot of trial, error, and iteration, and I know how valuable direct, tactical guidance can be. Coaching lets me give others what I wish I had more of early on: honest feedback, strong frameworks, a clearer narrative, and support in making smart, confident career decisions.
Work Experience
Investor
Outsiders Fund
2025 - Present
Investor
Venture Guides
2024 - 2025
Infrastructure software & cybersecurity
Product Manager - Payments
Citi
2021 - 2024
Education
Washington University in St. Louis
Bachelor of Science in Business Administration - BSBA, Finance and Entrepreneurship
Activities and societies: Honors in Innovation & Entrepreneurship; Dean's List Pam Kendall-Rijos Women's Mentor Program, Olin Student Code of Conduct Board, Student Entrepreneurial Program, Pi Beta Phi Economics and Interpersonal Skills
Olin School of Business
Bachelor of Science in Business Administration, Finance and Entrepreneurship
Economics and Interpersonal Skills