Kelly Toole

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In Conversation

What do you enjoy most about working with technical founders?

Kelly– Looking back on my years in engineering, my most vivid memories are of the team coming together creatively to overcome an unforeseen hurdle. In some cases, these challenges were purely technical. In others, they were roadmap or management related. I find it energizing to be able to leverage that experience to support founders as they navigate their own challenges. I'm grateful to be a partner who can relate to that journey in some way.

How has your own career journey impacted the way you think about your role as an investor?

Kelly– While taking an entry-level programming course in college, a TA asked if I'd be up for a chat over coffee. She was encouraging women to consider majoring in computer science and thought I'd make a good candidate. Our conversation made a lasting impact, and sure enough, three years later, I graduated with a CS degree. There have been many pivotal moments like these in my career. These similar moments happened at Apple, with colleagues and mentors, as well as at Index, when a Stanford classmate, Bryan, offered to introduce me to the team.

I think about our position as investors as an opportunity to meaningfully contribute to a founder's journey through intentional moments and actions like these– actions that are at varying degrees and scales but nonetheless aim positively to affect both the journey and the outcome.

We've heard you're a thrill-seeker. Tell us about these adventures.

Kelly– I don't know if "thrill-seeker" is quite right. I'm not chasing the rush of adrenaline, for example. What I enjoy is the sense of personal growth that stems from pushing myself outside of my comfort zone. Whether that happens while surfing bigger waves than I'm used to, following brave friends up a climbing route in Yosemite, or continuing to try wing foiling after failing for the millionth time, there is no better feeling than showing yourself that you can do something you thought was impossible. That's the feeling I like to chase. If you have an outdoor adventure you think I should add to my list, I'm all ears!

Kelly is a technology investor with particular excitement for those that create a crisp developer and user experience.

Before joining Index, Kelly was a software engineer and engineering manager at Apple. She worked on a variety of teams including Health Software, Applied Machine Learning, and iOS Systems. Kelly graduated from Stanford University with a B.S. in Computer Science with a focus in Systems. In her free time, Kelly enjoys sailing, surfing, kiting, and most other activities involving the ocean or mountains.