Medallion

Sierra

Medallion

Medallion charges healthcare organizations a subscription based on the number of providers being managed. The platform handles initial credentialing (verifying a new provider) and ongoing monitoring (ensuring licenses stay current, no disciplinary actions arise).

The value is measured in speed and cost savings. Credentialing departments at hospitals can cost millions annually in staff salaries.

Medallion replaces much of that manual labor with software. Faster credentialing also means faster time-to-revenue — a doctor who can start seeing patients weeks earlier generates revenue weeks earlier.

The platform also manages payer enrollment — getting providers into insurance networks — which is a related but separate bureaucratic process that's equally painful and equally automatable.

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.

Medallion

Derek Lo was working in healthcare operations when he encountered credentialing — the process of verifying that healthcare providers have the proper licenses, education, training, and malpractice history to practice medicine. Every doctor, nurse, and therapist in America must be credentialed before they can see patients at a new facility or join an insurance network.

The process was absurdly manual. It involved contacting medical schools, state licensing boards, previous employers, malpractice insurers, and the DEA — often by fax or mail.

A single credentialing verification could take 90-180 days. Healthcare organizations employed entire departments of people doing nothing but chasing down verifications through a patchwork of government databases, phone calls, and paper forms.

Lo founded Medallion in 2020 to automate this process. The platform connects directly to primary sources — state licensing boards, the National Practitioner Data Bank, DEA databases, and medical school registries — and pulls verification data automatically.

What used to take months of manual work now takes days or weeks.

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.

Medallion

Medallion grew by targeting healthcare organizations that were drowning in credentialing backlogs. Telehealth companies scaling rapidly during COVID were the first ideal customers — they needed to credential hundreds of providers quickly across multiple states, and the manual process couldn't keep up.

The platform expanded to hospitals, health systems, and staffing agencies that manage large provider networks. Each customer type faces the same fundamental problem: too many providers to credential, too few staff to do it, and too many regulatory requirements to track manually.

Integration partnerships with HR systems and practice management platforms drove distribution. When Medallion plugs into a health system's existing tech stack, the switching costs climb and the data integration deepens.

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.

Medallion

Healthcare is notoriously slow to adopt new technology. Decision-makers at hospitals and health systems are risk-averse and procurement cycles are long.

Selling enterprise software to healthcare organizations requires patience, compliance certifications, and relationships that take years to build.

The credentialing ecosystem involves hundreds of independent data sources — each state licensing board has its own system, formats, and response times. Building and maintaining connections to all of these sources is operationally complex and requires constant updating as boards change their processes.

Competition from established credentialing verification organizations (CVOs) and legacy software providers means Medallion is displacing existing processes and vendors, not entering a greenfield market.

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.

Medallion

Medallion Credentialing — automated primary source verification of healthcare provider qualifications including licenses, education, training, and malpractice history. Medallion Monitoring — continuous license and exclusion monitoring that alerts organizations when a provider's credentials change or expire.

Medallion Payer Enrollment — automated management of insurance network applications and re-enrollments across multiple payers. Medallion Provider Network Management — a unified platform for managing the complete provider lifecycle from recruitment through credentialing to ongoing compliance.

Medallion Analytics — dashboards showing credentialing pipeline status, bottleneck identification, and compliance metrics.

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.

Medallion

Sequoia Capital led the Series B. Optum Ventures (part of UnitedHealth Group) invested — a significant strategic validation from the largest healthcare company in America.

Tiger Global and GV (Google Ventures) participated in earlier rounds.

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.