Dandy

Sierra

Dandy

Vertical SaaS plus manufacturing. Dandy provides dental practices with intraoral scanners (often subsidized or free to eliminate the switching cost), cloud-based software for managing cases, and its own network of digital dental labs that manufacture the final restorations.

Dentists pay per case — each crown, bridge, veneer, or implant restoration is priced individually. The margin comes from manufacturing efficiency: digital workflows are faster, more precise, and require less manual labor than traditional hand-sculpted methods.

As volume grows, Dandy's labs get more efficient and per-unit costs drop. It's the classic razor-and-blades model — give away the scanner, make money on every restoration.

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.

Dandy

Henry Stott was a repeat entrepreneur who had previously co-founded a tech company in the UK. When he looked at the dental industry, he saw a $15 billion lab market that was shockingly analog.

Here's how it worked: a dentist jams a tray of gooey putty into your mouth, waits for it to harden, mails the physical mold to a dental lab, where a technician hand-sculpts your crown out of ceramic. Turnaround: 2 to 3 weeks.

Error rate: high. Patient experience: miserable.

The technology to do this digitally had existed for years — 3D intraoral scanners, CAD/CAM software, CNC milling machines — but nobody had stitched it into a seamless end-to-end platform for the average dental practice. Stott started Dandy in 2020 to be that platform.

Provide the scanner, build the software, run the lab — and make it so easy that any dentist can switch from analog to digital without changing how they practice.

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.

Dandy

Land-and-expand with dental practices. Dandy gives practices the scanner for free or at heavy discount, which eliminates the biggest barrier to switching from analog.

Once a practice starts submitting digital scans, they become recurring revenue — every patient who needs a crown is a Dandy order. Sales team targets mid-size practices (3 to 10 dentists) that are high-volume but haven't invested in digital yet.

Referral programs where existing dentists recommend Dandy to colleagues. Geographic density strategy — build lab capacity in a region, then saturate practices nearby to optimize logistics and turnaround times.

Content marketing educating dentists on why digital is better, faster, and more profitable than analog workflows.

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.

Dandy

Dental practices are notoriously resistant to change — many dentists have used the same lab for 20 years and switching feels risky. The scanner hardware is expensive to subsidize at scale, creating a capital-intensive land grab.

Quality control across distributed manufacturing is hard — a crown that doesn't fit means a remake, an unhappy patient, and a dentist who might switch back to their old lab. Competition from established digital players like Align Technology and legacy lab companies investing in their own digital capabilities.

The dental industry is fragmented — 200,000+ practices in the US, mostly small businesses, which means enterprise-style sales don't work. Each practice is its own decision maker with its own habits.

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.

Dandy

Dandy Scanner — provided to dental practices, captures a full 3D digital impression of the patient's mouth in minutes. No more putty molds.

Cloud-based case management platform where dentists submit scans, approve designs, and track orders. AI-powered restoration design that generates crown and veneer designs automatically from 3D scans, reducing turnaround from weeks to days.

Digital dental lab network with automated CNC milling and 3D printing for manufacturing restorations. Shade matching technology using AI to color-match restorations to surrounding teeth.

Integration with practice management software so cases flow seamlessly from scan to delivery.

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.

Dandy

Investors include Bessemer Venture Partners, IVP, DST Global, and IA Ventures. Series C in 2023 valued the company at approximately $1.8 billion.

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.