Shopify

Sierra

Shopify

Shopify charges merchants a monthly subscription fee — $39/month for Basic, $105/month for Shopify, and $399/month for Advanced. Enterprise clients pay more through Shopify Plus.

On top of the subscription, Shopify takes a cut of every transaction processed through Shopify Payments (2.9% + $0.30, similar to Stripe). If merchants use a third-party payment provider, Shopify charges an additional 0.5-2% fee.

The genius of the model is stacking revenue. Subscription fees are the base layer.

Payment processing is the second layer. Then there's Shopify Capital (lending money to merchants), Shopify Shipping (discounted shipping labels), Shopify Email, the app store (Shopify takes 0% on the first $1M in app revenue, then 15%), and Shopify Balance (banking for merchants).

Every new service extracts more value from each merchant.

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.

Shopify

Tobias Lütke was a programmer from Koblenz, Germany who moved to Ottawa, Canada in 2002 because he fell in love with a Canadian woman. He wanted to sell snowboards online through a store called Snowdevil.

The problem was that every e-commerce platform in 2004 was absolute garbage. They were expensive, ugly, and painful to use.

Most required a computer science degree just to set up.

Lütke was a Ruby on Rails developer — one of the early ones, when Rails was still a brand-new framework. Instead of suffering through the existing tools, he just built his own e-commerce platform from scratch.

Snowdevil launched on the custom-built platform, and it worked beautifully. Other small business owners saw it and started asking if they could use the same software.

Lütke teamed up with Daniel Weinand and Scott Lake. In 2006, they launched Shopify as a product — a hosted e-commerce platform that let anyone set up an online store without knowing how to code.

The first year was slow. They had about 100 merchants.

But the product was so much better than everything else that word spread. By 2009, they had launched an API that let developers build apps and themes for Shopify stores, creating an ecosystem that would become one of their biggest advantages.

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.

Shopify

Shopify grew by being the anti-Amazon. Their pitch was simple: Amazon is a marketplace where you're one of millions of sellers with no brand identity.

Shopify lets you build your own brand, own your customer relationships, and control your destiny. "Arm the rebels" became their unofficial motto.

The app ecosystem was a multiplier. By letting third-party developers build apps, themes, and integrations, Shopify created a marketplace of 8,000+ apps that extended the platform's functionality infinitely.

Need email marketing? There's an app.

Need inventory management? There's an app.

This meant Shopify could stay focused on the core platform while the community built everything else.

The Shopify Partners program turned freelance developers and agencies into a sales force. Partners who built stores for clients earned recurring revenue from referrals.

Over 10,000 agencies worldwide now specialize in Shopify development. It's basically a franchise model for tech.

COVID was rocket fuel. When physical retail shut down in March 2020, every small business in the world suddenly needed an online store immediately.

Shopify's new store creation surged 71% in Q2 2020. The stock went from $400 to $1,700 in less than a year.

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.

Shopify

The Amazon problem looms over everything. Amazon controls roughly 40% of US e-commerce.

Every Shopify merchant competes against Amazon, and many of them sell on both platforms. Amazon can always undercut on price, offer faster shipping, and has nearly unlimited resources.

Shopify's entire business depends on convincing merchants that owning their brand is worth more than Amazon's convenience.

The post-COVID hangover was brutal. After the pandemic boom, Shopify's stock dropped 80% from its November 2021 peak.

The company had hired aggressively during COVID, expecting the e-commerce shift to be permanent at pandemic levels. It wasn't.

In May 2023, Lütke laid off 20% of the company — about 2,300 people — and wrote a public letter admitting he had bet wrong on how much of the COVID shift would stick.

The fulfillment pivot was expensive. In 2019, Shopify announced the Shopify Fulfillment Network — their plan to build a warehouse and logistics network to rival Amazon.

They poured hundreds of millions into it. By 2023, they realized it was a money pit that distracted from their core business.

They sold the logistics operation to Flexport and wrote off the investment. Lütke called it "taking the medicine."

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.

Shopify

Shopify Online Store is the core — build and run an e-commerce website. Shopify POS (Point of Sale) handles in-person retail with card readers and inventory management.

Shopify Payments is the built-in payment processor powered by Stripe. Shop Pay is the accelerated checkout — it saves customer info so returning buyers can check out in one tap.

Shopify Capital provides cash advances and loans to merchants based on their sales data. Shopify Fulfillment Network was their attempt to compete with Amazon on shipping (they scaled it back in 2023).

Shopify Markets handles cross-border selling — currencies, duties, and translations. Shopify Audiences uses anonymized data to help merchants find new customers on ad platforms.

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.

Shopify

Bessemer Venture Partners, FirstMark Capital, Felicis Ventures, Georgian Partners, OMERS Ventures

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.