Sierra: Enabling every company to elevate their customer experience with AI

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Hi 👋, this is the Today in AI Newsletter: The weekly newsletter bringing you one step closer to building your own startup.

We analyze a cool, industry-shaping AI startup every week, with a full breakdown of what they do, how they make money, how much they’ve raised, and the opportunity ahead. 

Let’s get to the good stuff in this email: 

• This startup is enabling every company to elevate their customer experience with AI ☄️ 

• Their founders have been execs and chairs at companies like Google, Facebook, Salesforce and OpenAI

• They’ve just raised a $175M Venture Round at a $4.5B valuation 💰️ 

So what’s the startup and who are the founders behind it? Here’s the story of Sierra 📈

Sierra was founded in May 2023 by Bret Taylor and Clay Bavor with the mission to empower primarily consumer brands to build customer facing AI agents. 🤖 

These agents will help you on every aspect of customer service from finding your order to order returns and exchanges.

Essentially, Sierra is helping companies build branded AI agents for every single part of the customer experience. 😚 

Why is this super exciting? 🤔 Bret thinks we’re in an era of conversational software.

With GPT-4, we’ve crossed a quality threshold of effectiveness with conversational AI where now you’re able to have a conversation with a computer and it actually works.

You can have a super nuanced conversation with AI now and it will actually work. 

As a consequence, if you fast forward 5 years when you’re interacting with any consumer brand 🏢 (eg. insurance companies, phone companies or even car rental companies 🚘️ ), you will probably be having a conversation with an AI agent more than you’ll be clicking around on a website/app.

In 1995, the way you existed digitally as a business was to have a website/app. In 2025, the way you exist digitally is to have an AI agent.

With Sierra, Bret is trying to enable companies to build their own agents with their branding on it, and help them do everything their customers want to do. 💪 

Bret really thinks this is a new category of digital experience 🤯 and companies will want to be present in this world of conversational AI.

Backstory 👀

Flashback to when Bret Taylor was a little kid, he wanted to be Indiana Jones. He knew it wasn’t a job but that was the coolest example of an adult he’d ever seen. 😎 

Fast forward to high school, Bret thought he wanted to be an attorney - a real job he could actually pursue.

While in high school, Bret wanted to make some money so got a job working at a gas station getting paid $4.25 an hour (minimum wage at the time). 🪙 

At the same time, he’d hustled his way to making a website for a mechanic nearby in his hometown, and ended up getting paid $400 for that. 🤑 

He ended up quitting the gas station job the next day and started making websites for local businesses in his hometown. 💻️ 

Most of these websites actually endured for decades. The local florist, for example, didn’t really need to update their website often or make it fancy since 90%+ of their customers lived in the area.

A combination of his accidental entrepreneurial experience and going to Stanford during the dot com bubble got him in love with building in tech. 🧑‍💻 

It was one specific class he took in his first semester at Stanford: CS106a, that got him obsessed with software. He started building in class, then even in his spare time.

After doing both a Bachelors and Masters in CS at Stanford, Bret joined Google super early on and co-created Google Maps, and the Google Maps API. 🗺️ 

This is when he met Clay Bavor (his future Sierra co-founder) who was in charge of Gmail and Google Drive. The 2 bonded over building software and became very close friends.

Bret then went on to:

• Found FriendFeed 🧑‍🤝‍🧑 - A social networking app (Acquired by Facebook in 2009)

• Serve as Facebook CTO for 3 years

• Found Quip 📱 - A mobile suite that enables you to collaborate on any device (Acquired by Salesforce for $750M in 2016)

• Served as co-CEO of Salesforce with Marc Beinoff

• Served as Chairman at Twitter when Elon was negotiating to buy it 💵 

All before founding Sierra. He is now also a Chairman at OpenAI…

Stats 📊

💸 Sierra has now crossed over $20M in annual revenue despite being founded less than 2 years ago.

💲 Some of their customers now include Sonos, SiriusXM, WeightWatchers and AG1, who have all experienced higher customer engagement & higher resolution rates with Sierra.

💰️ On October 28th 2024, Sierra raised a $175M venture round at a $4.5B valuation led by GreenOaks with participation from ICONIQ Capital and Thrive Capital. 

🫰 Previous investors include Sequoia, Benchmark and Conviction Partners who bring Sierra’s total raised to $285M.

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