Between Sales and Product: Building Out Self-Serve at Notion & Dropbox

Back in 2009, Kate Taylor was graduating from the University of Southern California in the midst of the recession — not the optimal time to be job hunting. She took a chance and sent a cold email to Marc Benioff (a fellow Trojan). Within 10 minutes, the founder responded and introduced a recruiter to Taylor, who ended up landing a role as a corporate sales rep.

That email kicked off what would prove to be an impressive career in tech. After leaving Salesforce to join Dropbox in 2012, she spent the better part of the next decade figuring out the company’s famous self-serve funnel and refining the product feedback loop, ultimately leading their SMB revenue and scaled sales operation. Fast forward to August 2020, when Taylor joined Notion as their new Head of Customer Experience, a role that combines products, sales and support to run what she calls the “front door experience” for customers.

Here on The Review, we’re struck by how Taylor has strung together a fascinating set of experiences, from the classic top-down sales motion she saw at Salesforce, to the bottoms-up adoption and viral growth loops that propelled Dropbox and Notion. She’s built a career that, as she puts it, has been focused on finding the balance between sales and product — a skill that’s in high demand these days. 

As founders are increasingly leaning into product-led growth and self-serve strategies, there are plenty of potholes to derail their progress. For both sales-driven companies that are intrigued by self-serve and bottoms-up businesses wrestling with when to layer on sales, Taylor makes for the perfect guide.

In this exclusive interview, she unpacks common traps and tensions, comparing and contrasting her experiences at Dropbox and Notion to offer up sound advice on finding the middle ground between sales and self-serve. She also delves into strategies for thinking through pricing and packaging, approaching product prioritization, and building a better customer experience.

From how Notion’s incredibly tight product feedback loop works, to the pricing experiments Dropbox learned most from in the early days, Taylor shares a treasure trove of helpful anecdotes and actionable tactics that will have founders and go-to-market leaders taking notes (in Notion we hope).

Thanks, as always, for reading and sharing!

-The Review editors

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