Operations Manager at Oscar Health and Founder of Negotiating the Terms, Nikita Singareddy Talks Advice on Running a Side Hustle






"Nikita Singareddy has a degree in Statistics and History from Columbia University. Nikita had no idea where she wanted to work after college and her internships reflect that: advertising sales for Pandora Radio, product management for NBC's Election Unit, and comms for the Tor Project (the world's leading privacy browser). Upon graduating, she joined IBM's Innovation Lab before transitioning to IBM Ventures. She now works in operations and strategy for Oscar Health, a $3B health insurance startup backed by Google, Goldman Sachs, and Thrive Capital.

On the side, Nikita runs a website - Negotiating the Terms - that raises the visibility of young women in venture capital. She has interviewed investors from Bain Capital Ventures, Sequoia, Lerer Hippeau, General Catalyst, RRE, and more. She also advises startups in Columbia's startup accelerator, Almaworks."


Meet Nikita Singareddy
What made you decide to transition to Oscar Health from IBM and how did you hear about the position at Oscar Health?

"As for why I switched.. I just caught the startup bug. My role at IBM allowed me to see the constraints of a corporate while also interacting with founders and their growth challenges. I wanted to be on the operating side of things.

My current role at Oscar also really appealed to me. My team runs pilot programs to improve the member experience, outcomes, and cost. We do things like digital health, virtual medicine, strategizing care delivery, and more. Being able to research, design, and develop a pilot program exercises a lot of different skills that are both technical and qualitative."

I was wondering what the application/interview process was like for consulting at IBM and if you started that position directly after graduating?

"I copped out a little going to IBM. I had offers from a few startups but thought consulting was less risk averse, so I threw my hat in the ring during the spring semester. IBM's consulting is vastly different to commercial due diligence, financial consulting, deals strategy that you'd do at a McKinsey or an LEK or a PwC."

During college, how did you land internships at Pandora, NBC, and Tor? What do you think made you standout from other applicants?

"Good question. I spent a lot of time networking and having coffees to get these roles.

As for product, I wanted to see if PM was the right thing for me. So I applied for a non-traditional PM role at a place like NBC versus FB or Google (and their APM programs). You can build skills at non-traditional workplaces that make you a stronger candidate if you DO want to go to a big tech firm or even a big startup that are quite competitive.

As for Tor, I also just directly sent an email to their Director. She happened to need a comms person at the time. You can get roles just by cold reaching out and showing your interest! Do that as much as you can. You'll stand out as someone who doesn't just go for opportunities in the conventional way."

I was wondering if you have any advice for a senior in college looking for a job?

"I cold emailed a lot of people directly. I had a clear and specific ask and always gave them times to chat (do anything you can to make life easier for them). I also demonstrated ways I might be helpful. That helped me a ton in my job search. And as always, strike while the iron is hot! Don't wait too long to apply or respond to emails.

True story: a friend of mine worked at a VC firm and they opened up applications for a role. More than 2000 applied. They were just overwhelmed and decided to look at the first hundred apps. Ever since I've heard that, and seen it in a few different ways, I always tell people to move quickly.

And to stand out have a sharp, eye-catching resume. Seriously. Especially if you're going to a bigger company, HR folks aren't the ones doing the hiring but they are the first line of defense. If you can have a clear, interesting resume, that'll draw someone's attention over the standard Word resumes people send in."

We have a lot of students who are interested in starting their own publications/blogs, telling stories, and spreading the amazing work of others....I'm curious if you have any tips on getting started. How did you get your first interview? How do you get readers? What do you think the most important things behind Negotiating the Terms are?

"Great question! You just have to go for it but always do your research first. I looked for a gap - I saw that there wasn't a publication raising the visibility of young women in VC (even though that community was growing). So I decided to do it.

You'll see from the early traction whether the thing you're doing is actually helpful. And the results have been unexpected in the best way. I've reached ~1000 subscribers now. I've interviewed some of the brightest women in venture capital. I've even had the opportunity to advise some startups and help VC firms source for diverse candidates.

I started NTT by interviewing a few people I knew personally (and as always, by cold emailing). Since my interviews have been shared across social media, I've received inbound requests from people wanting to be interviewed. I've also sought nominations from interviewees."

As a founder/someone who is in the startup community and interacts with a lot of other founders I know it can be somewhat intimidating to interact with VCs. With all of the women you interview for Negotiating the Terms, do you hear any good advice they have for founders who are pitching to VCs? And if so what are the most common pieces of advice you hear?

"I think people place too much emphasis on their decks. Fundamental questions for VCs - is this a billion dollar opportunity in a big / niche addressable market? What pain point is this product / company answering and does it have a natural moat / network effect that'll make it better than alternatives? How much do I believe in this founder and their team (and their ability to execute)? If you can demonstrate an answer to that in your first meeting and pitch, that's very appealing to investors.

My advice is also to pick the investors who know and are interested in your space. A generalist investor might not be the right investor but an ed tech investor will be. There are many more specialized early stage investors now. They will have the strongest post-investment support.

Good advice for founders: demonstrate that you're someone willing to accelerate the learning curve. If you can fail and recover quickly - that's a founder to invest in."

I know that a really small percentage of VC money goes to female founders. Do you think that by interviewing female VCs on Negotiating the Terms you're helping to change that?

"I hope so! I think part of the problem is a pipeline issue. There are a number female entrepreneurs but they often don't get funded by men (e.g. what does a 50 year old male partner know about black female hair care?). If I can raise the profile of women who will fund women, that's great. We are certainly seeing more of that. But visibility isn't the only problem. There are systemic barriers to women being entrepreneurs in general like lack of pre-k, little PTO for mothers, sexual harassment, etc. We need to improve access and empower women to be women. That will enable more female founders."

How do you make the time / energy to balance a full time job with your side projects as well?

"It is hard! I do think it's a sacrifice on your personal life even if you love it. But it's part of the personal brand and has helped me meet a lot of people :). You have to make time for yourself (working out, hanging with friends, etc.) but I try to make as much of my relaxation time = side hustle time."

JANUARY, 8 / 2019