Slack

GitPod

Slack

Slack uses a freemium model. The free tier gives you access to your most recent 90 days of messages and 10 app integrations.

That's enough to get hooked. Then Slack charges per user per month — $8.75/month for Pro, $15/month for Business+, and custom pricing for Enterprise Grid.

The beauty of the model is that one person signs up, invites their team, the team gets addicted, and suddenly the company is paying for 500 seats. It's a virus that charges rent.

GitPod

GitPod started as freemium: a free tier of monthly cloud hours, paid plans for more hours and bigger workspaces, and enterprise contracts with self-hosted and dedicated options. As Ona it shifted toward enterprise contracts for running AI coding agents inside a customer's own cloud, with governance and security controls.

It said enterprise annual recurring revenue quadrupled year over year before the rename. OpenAI acquired the company in 2026, and existing customer commitments continue to be supported.

Slack

Stewart Butterfield had already done this exact thing once before. In 2002, he was building a massively multiplayer online game called Game Neverending.

The game flopped but one of its features — a photo-sharing tool — became Flickr, which Yahoo bought for $35 million in 2005.

So in 2009, Butterfield did it again. He started a company called Tiny Speck to build another game called Glitch — a quirky, non-violent MMO where players collaborated instead of fighting.

The game was beautiful, weird, and a complete commercial failure. It shut down in November 2012 after never finding a big enough audience.

But the internal communication tool the Glitch team had built for themselves was something special. They had created a searchable, organized messaging system because email was driving them insane.

Every conversation was in channels. Everything was searchable.

Files were shared inline. It was everything email should have been but wasn't.

Butterfield looked at this internal tool and thought: this is the actual product. In August 2013, Slack launched in preview.

Within 24 hours, 8,000 companies had signed up. Within two weeks, it was 15,000.

The growth was so fast that Butterfield said it felt like "trying to drink from a fire hose."

GitPod

The GitPod team came out of TypeFox, a German developer tools company in Kiel behind the Theia cloud IDE framework. Sven Efftinge and his colleagues realized the biggest pain point was not the editor itself but the environment.

Developers spent hours configuring machines, installing dependencies and debugging "it works on my machine" problems.

They launched GitPod to provide instant, automated cloud development environments. One click from a GitHub or GitLab repo opened a fully configured workspace with dependencies installed and tools ready.

Johannes Landgraf, who became CEO, and CTO Christian Weichel later led the company through its rename to Ona in 2025 and its sale to OpenAI in 2026.

Slack

Slack grew almost entirely bottom-up. Nobody sold Slack to companies.

Employees adopted it on their own and then convinced their bosses to pay for it. One developer would start using the free version, invite their team, and within weeks the whole department was hooked.

IT departments would discover that half the company was already on Slack before anyone asked for approval.

The integrations strategy was genius. Slack made it dead simple for other software tools to plug into Slack.

Instead of checking Jira for bug reports, Salesforce for deals, and GitHub for code changes, everything pushed notifications into Slack. Slack became the operating system of work — the one app you kept open all day.

Word of mouth was the main growth driver. Slack didn't spend heavily on advertising early on.

They spent on making the product feel delightful. The loading messages were funny.

The emoji reactions were addictive. The search actually worked.

People genuinely liked using it, which is almost unheard of for enterprise software.

GitPod

GitPod grew through open source community adoption and one-click integrations with GitHub, GitLab and Bitbucket, where a "Gitpod" button on a repo launched a ready workspace. It later moved upmarket to banks and pharmaceutical companies that wanted cloud development under tight security.

In 2025 it bet the company on AI agents, renaming itself Ona and claiming its own agents were producing most of its merged code. That bet ended in a sale to OpenAI in 2026.

Slack

Microsoft Teams was the existential threat. When Microsoft bundled Teams for free with Office 365 in 2017, Slack knew it was in trouble.

Microsoft had 300 million Office users who could start using Teams without paying anything extra. Slack even took out a full-page newspaper ad welcoming Microsoft to the chat market — a bravado move that masked genuine fear.

By 2020, Teams had overtaken Slack in daily active users purely on distribution.

The pandemic was a double-edged sword. Remote work exploded demand for Slack, but it also exploded demand for Teams, Zoom, and every other collaboration tool.

Slack's growth accelerated but so did everyone else's. The window where Slack was the obvious default was closing.

Revenue growth started slowing. After years of 50%+ annual growth, Slack's growth rate dropped to the low 30s by 2020.

Wall Street punished the stock, which dropped from its IPO price. The writing was on the wall — Slack couldn't outrun Microsoft alone.

In December 2020, Salesforce announced it was acquiring Slack for $27.7 billion. Butterfield stayed on as CEO until 2023, then left.

GitPod

GitHub Codespaces, backed by Microsoft and GitHub's enormous distribution, was a direct competitor, and AWS stopped taking new Cloud9 customers in 2024, a sign of how tough the cloud IDE market was. Convincing developers to give up their carefully configured laptops proved hard.

Then AI coding tools threatened to make the whole category a feature. GitPod's answer was to reinvent itself as Ona, an AI agent platform, and ultimately to sell to OpenAI in 2026 rather than compete alone.

Slack

Slack is the core messaging platform — channels for teams, direct messages, threads for focused discussion, and huddles for quick voice/video calls. Slack Connect lets you message people at other companies directly through Slack instead of email.

Slack Canvas is a built-in document editor for notes and wikis right inside channels. Workflow Builder lets non-technical users automate repetitive tasks without writing code.

The App Directory has 2,600+ integrations — connect Google Drive, Salesforce, Jira, GitHub, or basically any tool your company uses.

GitPod

Before 2025: cloud development environments, instant pre-configured workspaces defined in a .gitpod.yml file, with prebuilds and support for VS Code and JetBrains, plus a self-hosted enterprise option. As Ona (since September 2025): a platform for running software engineering AI agents in secure, sandboxed cloud environments, with VS Code in the browser and access from phone, tablet or laptop.

Since August 2026 the technology is part of OpenAI's Codex team.

Slack

Accel Partners, Andreessen Horowitz, Social Capital, GV (Google Ventures), SoftBank, Dragoneer Investment Group

GitPod

Speedinvest led the $3 million seed in October 2020, with Crane Venture Partners and Vertex Ventures US. General Catalyst led a $13 million round in April 2021.

GitHub founder Tom Preston-Werner led the $25 million Series A in November 2022. Total funding was about $41 million.