Toby Espinosa (VP of Ads, DoorDash) On DoorDash's Secret Sauce

A conversation with a DoorDash VP on lessons learned scaling from 10,000 deliveries on a Friday to over 2 billion deliveries in a year

Couldn’t be more excited to release the first Steelhead podcast episode with my good friend Toby Espinosa, VP of Ads at DoorDash.

Toby is a rare talent who started at DoorDash 9 years ago launching markets across the US. He spearheaded deals with some of the largest restaurant chains in the US including McDonalds, Chipotle, Chick Fil A, to name a few. Now, he’s leading a new business unit at DoorDash - Ads and Its Growth Services.

In our conversation Toby and I talked about:

- How, despite an aversion to sales, Toby ended up in a sales role at DoorDash (and what this means for people trying to find their way in their careers)

- Perseverance. Toby was rejected from 15 companies and twice from DoorDash before landing his first job as a launcher in 2015

- 3 great pieces of advice for Toby’s 25-year-old self just getting started in his career - it’s ok to feel lost, get into the “mud”, and follow your superpower

- B2B2C product market fit - what it is, how it’s different from other models, and the importance of incentive alignment in a model with multiple players

- How DoorDash thinks about layering on new products to continue growing - The pros and cons of operating a “bits and atoms” business - one where there are both software (bits) and real-world (atoms) components

- Toby’s favorite burrito in SF, the most underrated travel destination, content that most changed his view of business, and more in a quick-fire Q&A

- And as always, Toby’s “Steelhead” goal in life - something that’s hard and will take a long time, but will be well worth the effort

If you enjoy the video, subscribe to the Steelhead YouTube channel! Production quality will improve over time ;)

I look forward to publishing more of these conversations in the months and years to come as Steelhead continues to be a mechanism to explore company building and investing with incredible people.

-Erik