Shimin Ooi

San Francisco
Biography In Conversation

Shimin focuses on venture and growth across SaaS and AI applications. She’s excited about meeting outlier founders who are building products that truly delight customers. She enjoys learning about founders’ unique characteristics, their founding stories, and the empathy they have for their current and future customers.

Prior to Index Ventures, Shimin was the Head of Strategic Finance and Business Operations at Pilot, leading the product launch of two core products as well as several business initiatives including partnerships, comms, M&A, and other GTM initiatives. Before Pilot, she was an Engagement Manager at McKinsey working with tech and healthcare companies to help them solve strategic and operational problems. Before that, she also held roles at Goldman Sachs and JP Morgan.

Shimin graduated with highest honors from Princeton University with a B.A. in public policy and finance. In her free time, she enjoys walking her dog (find him @beauthelittlebear), playing board games, traveling, and learning new languages (4 down, more to go!).

When did your interest in entrepreneurship emerge?

SHIMIN – I was born in Singapore and spent most of my childhood there before moving to the U.S.. Living at the intersection of where East meets West in Asia, I was influenced by the rapid advancement of technology and fascinated by businesses—how they operated and how they scaled so quickly. I held my first garage sale in elementary school and even started a T-shirt business in high school that ended up selling several thousand shirts.

What was your journey into venture?

SHIMIN – Even though I loved math and science and considered becoming a doctor, I decided to follow my interest in business and joined McKinsey. I got to work with the largest corporations in the world and help business leaders solve critical problems. Then, Pilot reached out and I fell in love with what the founders were trying to build. In that job, I wore many hats, from developing and launching new products, to negotiating partnerships and fundraising, and weathered epic highs and lows.

When I thought about investing, I worried that I didn’t fit the stereotypical mold of a VC. However, once I talked to the Index partners, and they shared how they approached venture in their own way, I knew there was a place for me at the firm.

What are some of the most interesting projects you worked on while at Pilot?

SHIMIN – During my time at Pilot I developed and launched two core products that were essentially mini startups in a larger startup. That meant I led all of the subfunctions around those products including product development, engineering, sales, marketing, billing, customer support, and more. R&D Tax Credits was the first product I launched, hitting $100k ARR within 3 weeks of launch and achieving >$1m ARR within 6 months. Ultimately I grew these products to millions of ARR and hired GMs for them before moving on to other projects. It was an incredible deep dive into the mechanics behind driving hyper-growth. I learned a ton about how to effectively manage different pieces of the business which informs how I evaluate businesses and guide founders.

What are your biggest learnings from your time as an operator?

SHIMIN – My father told me very early on: “Always optimize for learning. If you’re not learning, you need to do something different.” I’ve followed this advice throughout my life, and consistently sought out opportunities where I can push myself rather than take the more comfortable path. This was never more true than during my time at Pilot.

From developing, launching, and running new core products, to growing partnerships to be one of our largest marketing channels, to launching new pricing and packaging, I tackled meaty challenges alongside an incredible team. I experienced firsthand how to sell a new product and differentiate from the competition, along with the thousands of steps required to successfully deliver the product to customers. I dealt with the difficulties of balancing competing priorities when designing simple and elegant pricing and packaging. Ultimately I learned to build something from scratch simply based on an idea and passion to see it through.

How do you think about the investor/founder relationship?

SHIMIN – I want to be the partner who always shows up and helps founders think through their problems. I’ve loved being in the trenches with visionary leaders, being the first call they make when they want insightful advice or need help. It’s also extremely rewarding to have both a front row seat and a role to play in supporting technologies that are driving societal change and solving important problems.

What are you on the lookout for when investing?

SHIMIN – The collision of passion, intelligence, and ambition—people who care deeply about something, to the point where they might be seen as unconventional or going against the grain. I look for people who have the grit to persevere. Because I’ve witnessed how difficult and all-consuming entrepreneurship is, and have scaled a startup myself, I look for founders who know that entrepreneurship isn’t always going to be “upwards and to the right.” I’m looking for founders who are building lasting companies that will shape history.

What is some advice you would give to entrepreneurs?

SHIMIN – Every entrepreneur will face the same question of resource scarcity. They will have multiple directions to take their startup and infinite things they could be doing at any point in time: When to build a product feature? Whether to hire a GTM role now or later? It’s important to prioritize the use of their resources in a thoughtful, disciplined way, which can be challenging for people who are dreamers by nature.

Secondly, entrepreneurs have become comfortable with the idea that, whether a company is successful or not, the work never ends. There will be a new crop of challenges at each stage, and their goals might change when they’re the founder of a 10-person startup versus the founder of a 1,000-person startup. They have to be prepared to build and rebuild over and over again.

How do you prioritize your time?

SHIMIN – For everyday decisions, I try to manage my schedule so that I’m able to get the most use out of my time. For bigger decisions, I ask myself: “will this decision matter in 10, 30, or 50 years?” I call it my “maximisation” framework because I consider whether each decision will enable me to maximize my full potential.

How do you manage failure?

SHIMIN – I’ve made a ton of mistakes and experienced failure repeatedly. I think the most painful mistakes I’ve made were when I hired people that ended up being a bad fit. I tried to give them the benefit of the doubt, even when I knew in my gut it wasn’t working out. Founders make this mistake often because recruiting can be so difficult and they’d rather “make do” than let someone go. It’s not about being right all the time, because no one is, and I think it’s ok to make mistakes as long as you learn from them.

What is your favorite book?

SHIMIN – This is a hard question, since my favorite book changes from week to week! My sister used to say that I would rather read than eat. I almost always choose fiction over nonfiction, and love stories that have an underdog, some fantasy element, and a happy ending.