By Sam Dore  • May 10, 2024

Taking the Leap: panel insights from startup operators who took the leap from big tech

On May 1st, we gathered our Leap community for an inspiring and informative panel discussion featuring Margaret-Ann "MA" Seger (Head of Product, Statsig), Nancy Wang (Fmr. Director & GM, AWS Data Protection), and Harris Chalat (Founder, Muir AI.) Our speakers’ diverse experience offered insights into the challenges of transitioning into startups and operating within entrepreneurial environments. These include when to make strategic pivots, how to center customer learnings, and the importance of resilience, adaptability, and community support.

Some highlights from the event:

When to make the leap:

I just didn't feel like I was working on the right problem. I felt this desire to find ways to have an impact, specifically in sustainability, to significantly reduce greenhouse gas emissions. My co-founder Peter and I kept in touch ever since school and continued to discuss how we could do something meaningful. We convinced each other that starting a business was the best way to do that. - Harris

Startups are nothing but uncertainty and grind. You're never gonna be ready. It's never a perfect time. Kids are gonna happen. Life is gonna happen. Moves are gonna happen. You just need to do what's gonna make you happy, ultimately. - MA

I try to really encourage people to ask themselves, “Why not? Why not have that experience? Why not go and see if it's fit for you?” For talented people, especially in an area like Seattle with an ecosystem that can support you, it's worth that shot. - Nancy

Tough moments along the way:

My wife was two weeks from her due date at the end of June last year. We were running with a team of four then, trying to raise seed financing and close a Fortune 500 company. A lot was going on, and there were a lot of questions like, “Is this right? Is this going to happen? Are we going to hit our end of the runway, which was coming up, and have to ask the two employees we were working with to work without salary? Will I have a job and a son simultaneously, or will I be an unemployed father?”

Grit or perseverance is a necessary aspect of starting a company. You need to continue to push, and if you trust in what you're doing and are systematic and driven in your approach, you will continue to work towards that end goal. - Harris

Customer discovery:

First-time founders care about product; repeat founders care about distribution. Many of us are on the tech side of big or small companies. We benefit from riding the coattails of an established business with a clear business model. We build fun tech. Until you're out trying to build something from scratch, you don't realize how hard it is to create a sustainable business model, which hinges on that distribution component, like GTM. If you're on the tech side, you may have blocked that out and said, “Yeah, not my problem.” It is your problem if you're at a startup. - MA

Make sure that you're focused on the problem, not the solution. It's like one aspect. One of the things I learned in the last years is to be more forward in talking about price. Price is a strong indicator of how much a customer actually cares about what you're building. - Harris

Pricing is a one-way door. Once you come up with something, you can't really raise it, right? You can only lower it…You really do have to talk to people who actually buy the product to understand how much of a budget they have. - Nancy

Career development:

You can definitely start a career in tech from “nontraditional” paths, whether it's finance professionals—investors or bankers—who go on to make an impact on fintech or healthcare professionals now going into health tech. You have insight into the problem, and at a startup, the delivery of services or impact on lives is just really that much more impactful than within a large company. - Nancy

Having done it in reverse, where I started my career in big tech and then did startups, in hindsight, I wish I'd flipped it. There is no faster career accelerant than joining a startup. If you're optimizing for impact and growth, I think it's a no-brainer. It’'s gonna feel un-glamorous relative to the old life [at a big company], but it's deeply fulfilling. - MA

Leap is a partnership between Madrona Venture Labs and Madrona to build a community of high-potential entrepreneurs, introduce them to the growing and vibrant local startup ecosystem, and help them build relationships with fellow innovators, experienced builders, industry experts, and top VCs.

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