Hello Generalist
Interview

Pallavi, Former COO at Chargehound (YC & Khosla backed, acquired by Paypal)

canva headhshot of pallavi from presentation

Pallavi Kuppa-Apte is fresh off of an 8 year tour as Chargehound’s COO, a chargebacks automation tool that Paypal acquired in 2021. Pallavi is truly that girl — she lead the team as they scaled, raised millions, and went through their acquisition, and still somehow remains an absolutely normal, delightful human to talk to.

I loved hearing her honest stories about conference chaos (reminded me of my first time building a booth at SxSW 🥴), and her reminder that “people want to buy from other people.” Hope you enjoy!

Drop 1. Compete with legacy players by embracing your scrappiness

I bought 300 balloons, filled a cooler with La Croix, set up a dog donation offering. Our booth had a home spun feel, but it turned out that it was an amazing differentiator for us. We stood up the booth for less than $2k, and got easily $2M of lead gen.

Take it back to your team:

  • Are you letting over-preparation and perfectionism prevent you from showing up in larger arenas?

  • How might you embrace being a small, scrappy team? People want to buy from other people. What are new creative ways you could tell your story?

  • Where do you mask or cover up that you’re actually a team of 1 or 3 people? Are you pretending to be a bigger company than you are? Why?

Drop 2. Your first customers are the people you already know

Our first real, paying customers were all YC batch mates. The first learning was, you don’t have to shoot for the moon in your first sales outreach. Going for that low hanging fruit is where you’re going to get the most validation.

Take it back to your team:

  • Have your friends and supporters heard your pitch? They’ll be the most open to giving you time and feedback, and often, will be your first buyers.

  • What networks are you a part of where you could partner, co-list, or support each other mutually? Is there low hanging fruit you haven’t explored?

  • Are you focused on “building the playbook,” or are you instead just out there, talking to people, testing a bunch of things? The latter will inform the former.

Drop 3. Tradeoffs to maintain your MVP mindset as you scale, from product to ops process

The prospect told us that unless we add a manual review, they wouldn’t be able to use our product. This was our biggest customer to date by a big multiple; our team worked overtime to push out the feature, we closed the deal, and that manual review feature became a key selling point. If we tried to build that feature from the get go, we wouldn’t have built the actually useful feature that we ended up pushing out.

Take it back to your team:

  • Is your product roadmap rooted in customer feedback? What about your product backlog? How might you integrate more customer feedback in your work?

  • What process creep has made it’s way into your team? How might you help your leaders give up heavy process in exchange for more valuable work?


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