Warby Parker

Sierra

Warby Parker

Vertically integrated direct-to-consumer eyewear. Warby Parker designs frames in-house, works directly with manufacturers, and sells through its website, app and its own stores, skipping the traditional licensing and wholesale markups.

Glasses still start at $95 including basic prescription lenses, with upgrades for progressives and special coatings. Revenue comes from prescription glasses, sunglasses, contact lenses and eye exams in stores.

What started online-only now runs mostly on physical retail, with 323 stores at the end of 2025. Net revenue was $872 million in 2025, and it was the company's first full year of net profit.

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.

Warby Parker

Dave Gilboa lost a $700 pair of glasses while backpacking before starting at Wharton, and replacing them was so expensive he spent his first semester squinting. He complained about it to classmates Neil Blumenthal, Andrew Hunt and Jeffrey Raider, and they started digging into why glasses cost so much.

The answer was Luxottica, the Italian giant that owned Ray-Ban, Oakley, LensCrafters, Sunglass Hut and Pearle Vision, the vision insurer EyeMed, and licenses for luxury brands like Chanel and Prada. One company touched almost every step from design to retail.

With a small seed check from Wharton's Venture Initiation Program, the four launched Warby Parker in February 2010, selling prescription glasses online for $95. GQ called them "the Netflix of eyewear," they hit their first-year sales target in about three weeks, and they built a waitlist of around 20,000 people.

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.

Warby Parker

The DTC playbook: build a beautiful brand, price far below incumbents, and tell a story about why the old way was a rip-off. Home Try-On, five frames mailed to try at home for free, doubled as marketing as customers posted photos asking friends to vote.

"Buy a Pair, Give a Pair" gave the brand a social mission, and by 2025 it had distributed more than 20 million pairs through its partners. Then it went physical, opening stores that now drive most sales, with 47 new stores in 2025 and about 50 more planned for 2026.

It added eye exams and Scout contact lenses to sell more to each customer, and in 2025 partnered with Google and Samsung on AI-powered smart glasses.

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.

Warby Parker

EssilorLuxottica, formed when Luxottica merged with the world's biggest lens maker, is still a giant with resources Warby Parker cannot match, and it now sells the Ray-Ban Meta smart glasses. After the 2021 direct listing the stock fell more than 70% from its highs as the direct-to-consumer bubble deflated.

Opening dozens of stores a year is capital intensive, and each one has to earn its keep. Cheaper online rivals like Zenni and EyeBuyDirect undercut it on price.

And people only buy glasses every year or two, so the business depends on keeping customers for a long time. Its big new bet, AI glasses with Google, puts it head to head with Meta.

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.

Warby Parker

Prescription eyeglasses starting at $95 including basic lenses — the product that broke the Luxottica pricing model. Home Try-On — pick five frames online, receive them in a box, try them at home for free, return what you don't want.

Progressive lenses and blue-light-filtering options for higher-end needs. Prescription and non-prescription sunglasses.

Scout contact lenses — Warby Parker's daily disposable contact lens brand. In-store eye exams with licensed optometrists.

Virtual Try-On using iPhone face-scanning technology to see frames on your face through the app.

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.

Warby Parker

Tiger Global Management led the $12.5 million Series A in 2011 and the $60 million Series C in 2013, and was still sitting on a stake worth about $850 million at the direct listing. General Catalyst led the 2012 Series B.

T. Rowe Price led the 2015 and 2018 rounds, and D1 Capital Partners and Durable Capital Partners backed the $245 million raised in 2020 at a $3 billion valuation.

American Express and J.Crew's Mickey Drexler were also early investors. The company went public on the NYSE through a direct listing on September 29, 2021.

In 2025 Google agreed to put up to $150 million into a smart glasses partnership, part of it as an equity stake.

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.