
Jiya S.
5.0
(7)
2 followers
Studied at Washington University in St. Louis
Works at Outsiders Fund
Successful clients at
Available Thursday at 3:30 PM UTC
Usually responds within 48 hours
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 an investor at Outsiders Fund in New York, where I focus on early-stage software investing. My path into venture wasn’t traditional; I started in product at Citi, consulted for early-stage startups, and ran my own business in college. I was able to learn how to effectively market my "untraditional background" to break into VC without a banking background or a clear template to follow. Because I navigated that process the hard way, I’ve become someone people naturally come to for guidance. I’ve received multiple VC offers and understand how firms actually hire, where roles surface, and which networking strategies work versus waste time. I help candidates break into venture by giving practical advice on sourcing jobs, surfacing networks, building a narrative, and preparing for every part of the interview process-- cases, theses, technical questions, and behavioral conversations. I’ve learned firsthand how opaque this industry can be, and that’s why I care about making it easier for others. Whether someone is exploring VC for the first time or preparing for partner interviews, I bring the same perspective I used in my own experiences.
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
7 Reviews
Overall Rating
5.0
Jiya has helped clients get into these companies: