Figma

Sierra

Figma

Figma uses a freemium model. Individual designers can use Figma for free with up to three active projects.

Teams pay per editor per month — $15 for Professional, $45 for Organization and $75 for Enterprise. Viewers are always free, which was revolutionary.

In Sketch, if a developer wanted to inspect a design, they needed a license. In Figma, you just send them a link.

This "free viewers, paid editors" model was genius because it turned every designer into a distribution channel. A designer joins a company, uses Figma, invites 50 engineers and PMs to view files, and suddenly the whole company is embedded in the Figma ecosystem.

When decision-makers see everyone already using it, upgrading to a paid team plan is automatic.

Revenue grew from essentially nothing in 2018 to over $600 million a year by 2023, and past $700 million by the time the company went public in 2025. The company was profitable by mid-2022 — unusual for a venture-backed startup.

They achieved this without a massive enterprise sales team. The product spread bottom-up through organizations, designer by designer, team by team.

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.

Figma

Dylan Field dropped out of Brown University in 2012 after interning at Flipboard and winning a Thiel Fellowship — Peter Thiel's program that pays students $100,000 to leave college and start something. His co-founder Evan Wallace was a Brown classmate and graphics programming wizard who'd built impressive WebGL demos that proved browsers could handle complex visual work.

Their original idea wasn't even a design tool. Field initially wanted to build a flight search engine, then pivoted to drone photography, before landing on the insight that would define Figma: professional creative tools were stuck in the desktop era while everything else had moved to the cloud.

Photoshop, Illustrator, Sketch — all required downloads, all worked on local files, and none of them let two people work on the same file simultaneously.

The technical challenge was enormous. Nobody believed you could build a high-performance vector graphics editor that ran entirely in a web browser.

Field and Wallace spent three years — 2012 to 2015 — just building the rendering engine before they had a product anyone could use. They basically had to invent new technology for browser-based graphics processing.

The first public beta launched in December 2015, and designers immediately noticed something no other tool offered: real-time multiplayer editing, like Google Docs but for design.

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.

Figma

Figma grew almost entirely through product-led growth — the product was so good and so easy to share that it spread virally through design teams. Every shared Figma link was marketing.

Every viewer who saw a design file in their browser without downloading anything was a conversion event.

The "free viewers" decision was the single most important growth lever. Traditional design tools charged per seat.

Figma said: only editors pay, everyone else is free. This removed all friction from collaboration and meant that for every paying designer, there might be 10-20 free viewers — all of whom experienced the product and became advocates.

Community was the second engine. Figma's open plugin system and free template marketplace created an ecosystem that locked in users.

Designers built their workflows around Figma-specific plugins, teams built design systems in Figma components, and switching costs climbed. By 2022, Figma had become the default — not just a design tool, but the operating system for product design.

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.

Figma

The Adobe acquisition saga was the biggest test. In September 2022, Adobe announced it would acquire Figma for $20 billion — the largest private software acquisition ever proposed.

Designers panicked. Would Adobe kill Figma's culture?

Bloat it with features? Integrate it into Creative Cloud and ruin the simplicity?

The deal fell apart in December 2023 when European regulators signaled they'd block it on antitrust grounds. Adobe walked away and paid a $1 billion breakup fee.

Figma was independent again — but now had to prove it could grow into a $20 billion company on its own.

Competition is intensifying. Canva is pushing into professional design.

Adobe is rebuilding its own collaborative tools. And newer entrants are using AI to generate designs automatically, potentially reducing the need for traditional design tools altogether.

Figma's challenge is staying ahead in a market it created while expanding into adjacent categories like presentations, whiteboarding, and development handoff.

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.

Figma

Figma Design — the core browser-based interface design tool with real-time multiplayer collaboration, component libraries, auto-layout, and prototyping. FigJam — a collaborative whiteboard for brainstorming, diagramming, and planning that competes with Miro and Mural.

Dev Mode — a workspace specifically for developers to inspect designs, extract code snippets, and understand spacing and styling without bothering designers. Figma Slides — presentation software launched in 2024 that lets teams build slide decks using the same design tools and component libraries.

Community — a marketplace of free and paid design templates, plugins, and UI kits created by designers worldwide.

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.

Figma

Index Ventures led the Series A and has been involved in nearly every round. Greylock Partners was an early backer.

Kleiner Perkins and Sequoia Capital invested in growth rounds. Addition (Lee Fixel's fund) led the Series E that valued Figma at $10 billion.

After the Adobe deal collapsed, a 2024 tender offer valued Figma at $12.5 billion, and the company went public on the NYSE in July 2025 at a considerably higher price. Peter Thiel was indirectly connected through the Thiel Fellowship that funded Dylan Field's early journey.

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.