DoorDash

Sierra

DoorDash

DoorDash operates a three-sided marketplace connecting restaurants, delivery drivers (Dashers), and consumers. Revenue comes from three streams: commissions charged to restaurants (typically 15-30% of the order value), delivery fees and service fees charged to consumers, and DashPass subscription revenue ($9.99/month for free delivery and reduced fees).

The DashPass subscription is the retention engine. Over 18 million subscribers pay monthly whether they order or not, creating predictable recurring revenue.

Subscribers order more frequently (about 4x more than non-subscribers), increasing order volume.

Advertising is the emerging high-margin business. Restaurants pay for promoted listings and sponsored placements in the app.

This is essentially a search advertising business built on top of a logistics network. Ad revenue has grown to over $1 billion annually — and it's nearly pure profit because it costs almost nothing to display an ad.

Sierra

Companies pay Sierra to run their customer service with AI agents instead of hiring rooms full of humans. The agent talks to your customers over chat.

It answers questions. It processes returns.

It updates subscriptions. Here is the clever part.

Sierra charges based on outcomes, not seats. Brands pay when the AI actually resolves a problem, not just for having the software installed.

That pricing is unusual. Most software charges a flat monthly fee no matter what.

Sierra only gets paid when the bot does the job.

DoorDash

Tony Xu grew up watching his mother work multiple restaurant jobs after the family immigrated from Nanjing, China to Illinois. She washed dishes, waited tables, and cooked — sometimes all in the same week at different restaurants.

That experience gave Xu an unusual understanding of how brutally hard the restaurant business is.

At Stanford in 2012, Xu and classmates Stanley Tang, Andy Fang, and Evan Moore were in a startup class looking for a business idea. They interviewed over 200 small business owners and kept hearing the same problem: restaurants wanted to offer delivery but couldn't afford to hire drivers.

Domino's and Pizza Hut had fleets. Your local Thai place didn't.

Their solution was comically low-tech. They built a one-page website called PaloAltoDelivery.com, listed menus from local restaurants (without asking permission), and put their personal phone numbers on the site.

When orders came in, they drove the food themselves. The first order was pad thai from a restaurant in Palo Alto.

Within months, they were drowning in orders and realized this was a massive business. They incorporated as DoorDash in January 2013 and got into Y Combinator that summer.

Sierra

Bret Taylor had already done the impossible twice. He co-created Google Maps.

He later became co-CEO of Salesforce, chaired Twitter's board during the messy Elon Musk takeover, and became chairman of OpenAI in late 2023. Clay Bavor spent 18 years at Google, most recently running its Labs group.

The two friends left their big jobs in 2023 to build something together. They picked customer service on purpose.

It is the least glamorous corner of software. Their logic was simple.

Companies hate their support costs. Customers hate waiting on hold.

AI that actually resolves problems could fix both sides at once. They launched Sierra in February 2024 with $110 million from Sequoia and Benchmark.

DoorDash

DoorDash won the US market through obsessive focus on suburban and mid-market restaurants — the segments Uber Eats and Grubhub ignored. While competitors fought over Manhattan and San Francisco, DoorDash was onboarding every Chinese restaurant and pizza shop in Tucson and Des Moines.

By the time competitors noticed, DoorDash had locked up the majority of US restaurants.

The "last-mile logistics" expansion is the long game. DoorDash now delivers groceries (partnerships with Albertsons, Rite Aid), convenience items (DashMart dark stores), alcohol, pet supplies, and retail products.

The thesis is that once you have a network of drivers and a consumer habit of ordering through an app, you can deliver anything — not just food.

The Wolt acquisition for $8.1 billion in 2022 was the international play. Instead of grinding through country-by-country expansion, DoorDash bought the leading delivery platform in 23 countries across Europe and Asia.

Wolt brought strong unit economics and a beloved brand, especially in the Nordics.

Sierra

Sierra went straight for big brands, not tiny startups. SoFi, Ramp, ADT, Sonos and Brex signed up early.

By 2026 it said more than 40% of the Fortune 50 were customers. The trick was trust.

Enterprises are terrified of an AI bot going rogue and insulting a customer. So Sierra built guardrails and let each company control exactly how the agent behaves.

Bret Taylor's contacts did the rest. When the chairman of OpenAI calls a Fortune 500 CEO, they pick up.

Sierra hit $100 million in annual recurring revenue in November 2025, seven quarters after launch, and $150 million by February 2026. In April 2026 it launched Ghostwriter, which builds and deploys a new agent from a plain-English description.

DoorDash

Profitability has been the constant question. DoorDash lost money every year through its IPO and beyond, finally posting its first full year of profit in 2024.

The food delivery business has razor-thin margins — restaurants want lower commissions, drivers want higher pay, and consumers want lower prices. Squeezing profit from that three-way tension is incredibly hard.

Regulatory risk is real and growing. Cities and states have capped delivery commissions (New York City caps at 15% for delivery, 5% for marketing).

Worker classification lawsuits keep coming — are Dashers employees or independent contractors? California's Prop 22 temporarily settled this for California, but the debate rages everywhere else.

Each new regulation shaves margin.

Uber Eats is the forever competitor. Uber's massive ride-sharing network gives them built-in driver supply and brand recognition.

They're willing to lose money on Eats to keep their broader ecosystem sticky. DoorDash and Uber Eats together control about 90% of US delivery, and neither can afford to cede ground.

Sierra

Everyone is building AI customer service agents right now. Decagon has raised at a multi-billion valuation.

Salesforce, ServiceNow and Intercom all shipped their own agents. Sierra is not the cheap option.

It sells premium AI to giant companies that move slowly. The bigger risk sits underneath the product.

Sierra does not make its own AI models. It rents them from providers like OpenAI and Anthropic.

If those model makers decide to compete directly, Sierra's edge gets thin fast, and its co-founder chairing one of them only makes that question louder. A $15.8 billion valuation on roughly $150 million in revenue leaves almost no room for a stumble.

DoorDash

DoorDash Marketplace — the core food delivery platform connecting consumers to 390,000+ restaurant partners across the US, Canada, Australia, Japan, and Germany. DashPass — a subscription program offering $0 delivery fees and reduced service fees for $9.99/month.

The loyalty engine of the entire business. DoorDash Drive — a white-label delivery service that lets any business (not just restaurants) use DoorDash's driver network to fulfill their own orders.

Basically DoorDash as a logistics API. DoorDash for Business — a corporate platform for team meals, employee benefits, and office food programs.

Wolt — the European food delivery platform DoorDash acquired for $8.1 billion in 2022, now the company's international expansion vehicle.

Sierra

The core product is the Sierra AI agent. It is a branded customer service bot that companies deploy on their website, app, and phone lines.

It handles the boring stuff. Order tracking.

Refunds. Password resets.

Account changes. Sierra also built its own tools to test and monitor these agents so they do not make things up.

In 2024 the company added a voice version that talks to customers on the phone. In April 2026 it added Ghostwriter, a tool that builds and deploys a new agent from a plain-English description.

The whole pitch is one AI agent that carries your brand's name and never sleeps.

DoorDash

Sequoia Capital has been the most consequential investor, leading multiple rounds and backing Tony Xu from Y Combinator onward. Khosla Ventures, Kleiner Perkins, and SoftBank Vision Fund participated in growth rounds.

Y Combinator was the starting point (Summer 2013 batch). The December 2020 IPO raised $3.4 billion at a $39 billion valuation, making it one of the biggest tech IPOs of that year.

Sierra

Sequoia Capital and Benchmark wrote the first checks at launch in February 2024, $110 million between them. Greenoaks Capital then led both the $175 million round in 2024 and the $350 million round in September 2025.

In May 2026 Tiger Global and Google's GV led a $950 million round at a $15.8 billion valuation, with Benchmark, Sequoia and Greenoaks back in. That takes total funding to about $1.6 billion.

That is partly the product and partly Bret Taylor. Investors bet on founders who have already built billion-dollar things.