/ Research
How ChatGPT Enterprise, Claude Enterprise, and Cassidy compare at a glance
| Strategic Goal | ChatGPT Enterprise | Claude Enterprise | Cassidy |
|---|---|---|---|
Primary philosophy and positioning | One OpenAI workspace for employees' chat, Work, and Codex | Anthropic chat and agents for each employee's everyday work | Agents plus auditable Workflows for regulated, high-stakes work Win |
Time-to-value and implementation | Dedicated onboarding, with SSO and SCIM set in the admin console | Self-serve SSO and SCIM setup, plus Claude Academy courses | Prompt your way to a working Workflow, with our team helping you get it right Win |
Multi-step workflows and event triggers | Scheduled and event tasks for supported apps like Gmail, Slack, GitHub | Cowork schedules, plus Claude Code routines from API calls or GitHub | CRM, meeting, form, and ticket triggers, with every step auditable Win |
Model choice and provider flexibility | OpenAI models only | Anthropic models only | OpenAI, Anthropic, Google, and open source models, chosen per step Win |
Knowledge Base and company context | Company Knowledge toggled per chat; admins control app access | Projects scope files; enterprise search queries connected tools | Knowledge Base syncs continuously and grounds every Agent and Workflow Win |
Implementation support and onboarding | Dedicated onboarding and ongoing account management | Admin guide and Claude Academy courses; sales-assisted or self-serve | Solutions team, hands-on training, and support after launch Draw |
Public tutorials, templates and community | Large public base of ChatGPT tutorials, templates, and third-party guides | Large public base of Claude tutorials, prompts, and third-party guides | Its own library and team support, with a smaller public base Lose |
Governance, permissions and audit logs | SSO, SCIM, RBAC, EKM, Compliance API, IP allowlisting | Compliance API, audit logs, and OpenTelemetry monitoring | RBAC, SSO, and audit logs cover every Agent and Workflow run Draw |
Vendor lock-in and rollout at scale | Tied to OpenAI's models, roadmap, and workspace | Tied to Anthropic's models and roadmap | Model-neutral and system-neutral; easiest to scale and manage Win |
Consumer-style apps and extras | Polished mobile and desktop apps, plus extras like voice | Polished desktop app for personal everyday use | Focused on the team workspace, with fewer consumer-style extras Lose |
Everyday usability and learning curve | Familiar to employees who already know ChatGPT | Chat and Artifacts are well regarded for everyday ease of use | Same chat and models, with a newer interface for most employees Lose |
Best fit: team size and use case depth | Teams wanting one familiar workspace for quick, simple chat and coding | Teams standardized on Anthropic models for individual work | Regulated, high-stakes processes run the same way for everyone Win |
/ Data current as of October 2026
Looking for a broader view?
Everyday chat and agent experience
What it feels like to use each tool day to day, and what happens when a quick question becomes a process.
ChatGPT Enterprise
- ChatGPT runs across web, mobile, desktop, and native surfaces like Slack, Teams, and Office apps
- Chat, Work, and Codex cover ad hoc research, drafting, and coding
- Company Knowledge is turned on per chat and respects each user's source permissions
- Workspace Agents and Work handle longer tasks, with approval before actions in connected tools
Claude Enterprise
- Claude runs in chat, a desktop app, Office add-ins, and a Slack app in beta
- Chat and Artifacts support writing, analysis, and research
- Projects scope files and instructions to a specific piece of work
- Cowork extends chat into longer tasks, with local folders and a built-in browser
Cassidy
- Agents run in Slack, Teams, Chrome, Word, Excel, PowerPoint, and Outlook
- Chat and Agents answer everyday questions on leading models, with Artifacts and Projects, in a secure environment
- Knowledge Base context grounds every Agent, so everyone starts from the same shared source
- The same interface extends into governed Workflows, with no handoff to a separate builder
/ Testimonial
Multi-step workflows and event-triggered automation
What it takes to make a process run on its own, without someone opening a chat first.
ChatGPT Enterprise
- Workspace Agents run on a schedule or API trigger, and Work adds Gmail, Slack, and GitHub events
- Event triggers cover supported apps, and Enterprise admins decide whether they are enabled
- Workspace Agents can be created from templates, with admins controlling plugins and apps
- ChatGPT asks for approval before taking action in connected tools
Claude Enterprise
- Cowork runs scheduled tasks, and Claude Code routines start from API calls or GitHub events
- On legacy seat plans, scheduled tasks share one rolling window and weekly cap with chat
- Claude Code routines add their own setup path for technical teams
- The Compliance API and audit logs cover Cowork and Claude Code sessions
Cassidy
- CRM changes, meetings, forms, tickets, and events from connected apps start Workflows
- Scheduled Workflows do not compete with chat for one usage cap, and admins can exclude them
- Business teams wire up triggers in a no-code builder without engineering help
- Branching and approvals are built in, and each step is visible for review
/ Testimonial
Model choice and provider flexibility
Who decides which AI model does the work, and how much it takes to change that later.
ChatGPT Enterprise
- OpenAI models power ChatGPT, Work, Codex, and Workspace Agents
- Workspace owners set model access and defaults from an OpenAI-only list
- Switching means choosing among OpenAI's own models and modes
- Anthropic and Google models are unavailable inside the workspace
Claude Enterprise
- Anthropic models power chat, Cowork, and Claude Code
- Teams choose among Claude's own model options
- A task suited to another provider's model has to be handled in a different tool
- OpenAI and Google models are unavailable inside the workspace
Cassidy
- OpenAI, Anthropic, Google, or open source models can sit behind any Agent or Workflow
- The builder picks from a recommended models selector, and admins set what users can access
- Switch models when a better one ships, without rebuilding
- Mix providers across steps, such as Claude for drafting and a faster model for classification
/ Testimonial
Knowledge base, integrations, and deployment surfaces
How company context reaches the AI, and where employees actually use it.
ChatGPT Enterprise
- Company Knowledge searches connected apps, with citations and source permissions
- Users turn it on per conversation and choose which apps to search
- Admins control plugins and apps, and underlying app permissions still apply
- Native surfaces include Slack, Teams, Excel, Google Sheets, PowerPoint, and Word
Claude Enterprise
- Projects hold files scoped to a single piece of work
- Enterprise search queries connected tools such as Drive, SharePoint, Slack, and Gmail
- Role-based permissions limit which products and connectors each group can use
- Office add-ins and a Slack app in beta, with Teams reached through connector tools
Cassidy
- Knowledge Base syncs continuously from Drive, SharePoint, Confluence, CRMs, and meeting transcripts
- Projects scope files to a piece of work, while the Knowledge Base applies to every Agent and Workflow with no per-chat toggle
- Source permissions carry through, and apps like Salesforce, HubSpot, Zendesk, and Notion connect as equals
- Deploys natively in Slack, Teams, Chrome, Word, Excel, PowerPoint, and Outlook
/ Testimonial
Implementation, onboarding, and support model
What it takes to get this live, and who is around to help once it is.
ChatGPT Enterprise
- SSO, SCIM, RBAC, and workspace setup run through OpenAI's admin console and docs
- Admins configure the workspace, with agent templates and plugin controls speeding rollout
- Dedicated onboarding includes hands-on help with training and change management for eligible customers
- Ongoing account management continues after launch
Claude Enterprise
- Admin console setup is self-serve for SSO and SCIM
- Enterprise is available directly from Anthropic or AWS Marketplace, sales-assisted or self-serve
- An administrator guide and Claude Academy courses cover rollout
- Claude Code adds its own setup path for technical teams
Cassidy
- Describe an automation in plain language to get a complex use case live
- The person closest to the work builds and owns it, without waiting in an IT queue
- A dedicated solutions team designs and launches the first Workflows, with hands-on training
- Support continues as new Workflows get added, alongside self-serve Cassidy University
/ Testimonial
Governance, permissions, and audit logs
What IT has to manage once this is live across the company.
ChatGPT Enterprise
- SAML SSO, SCIM, and RBAC, with admin control of models, plugins, apps, and actions
- Compliance API covers conversations and app activity, with documented visibility for agent activity
- Admins manage agents, spend, and plugins from a central console
- Enterprise adds EKM, IP allowlisting, and data residency in ten regions
Claude Enterprise
- SSO, SCIM, and role-based permissions restrict products and connectors by group
- Compliance API covers chat, Cowork, and Claude Code sessions once a Primary Owner enables it
- Audit logs and OpenTelemetry monitoring are available on Enterprise
- Admins can set custom data retention
Cassidy
- RBAC and SSO cover every Agent and Workflow, including each trigger, step, and action
- Audit logs cover every Agent and Workflow run, so each step the AI takes is reviewable
- Admins manage Agents, Workflows, and usage caps from one place
- SOC 2 Type II, GDPR, HIPAA, and CASA validated controls, with no model training on your data
/ Testimonial
Where each platform wins
Each competitor has a real advantage. Here is where each one is the better fit.
When ChatGPT Enterprise is the better fit
ChatGPT Enterprise is the better fit for a company already standardized on OpenAI's models that wants one familiar workspace for quick, simple, team-wide chat, research, documents, and coding. The familiar ChatGPT UX, native surfaces, and OpenAI-led onboarding mean less change management at rollout.
Teams usually outgrow it when a business process has to run the same governed way every time, with an audit trail at every step.
When Claude Enterprise is the better fit
Claude Enterprise is the better fit for a company already standardized on Anthropic's models that wants a desktop app with local file access, Claude Code for developers, and a chat tool its team already likes.
Teams usually outgrow it when a process has to give the newest hire and the senior analyst the same result, with every step visible for audit.
/ Platform Recommendation
Choosing between ChatGPT Enterprise, Claude Enterprise, and Cassidy
Match your situation to the lists below. If most of one list describes your work, that platform is the fit.
Choose
ChatGPT Enterprise if…
- Your team already knows ChatGPT and wants one familiar workspace for quick, simple chat, research, and coding
- You are comfortable standardizing on OpenAI's models and its native Slack, Teams, and Office surfaces
- Your security team wants OpenAI's built-in controls, onboarding, and account management
Choose
Claude Enterprise if…
- Your team already knows Claude and prefers working in Anthropic's models
- You want a desktop app with local file access, or Claude Code, alongside chat
- Your security team wants Anthropic's Compliance API, audit logs, and OpenTelemetry monitoring
Choose
Cassidy if…
- Your work is regulated or high-stakes, and you need an audit trail at every step
- Part of your team prefers GPT and part prefers Claude, and you want both without picking one vendor
- New and better models keep arriving, and you want to switch to the best one without rebuilding Agents or Workflows
- You want one process to run the same way for every employee, built with enterprise governance in mind
Compare these platforms head-to-head
Continue exploring Cassidy
FAQ
Find answers to common questions about the platform, security, and getting started. Still have questions? Talk to our team!
Which is best for enterprise teams: ChatGPT Enterprise, Claude Enterprise, or Cassidy?
Cassidy. It is built for regulated and high-stakes work, with an audit trail at every step, Agents and Workflows in one place, and the right model chosen per step. ChatGPT Enterprise and Claude Enterprise suit quick, simple team-wide chat, and the same chat experience and models are available inside Cassidy's secure environment, with governed Workflows on top.
Which is best for regulated or high-stakes work: ChatGPT Enterprise, Claude Enterprise, or Cassidy?
Cassidy is built for regulated industries and high-stakes work such as insurance, manufacturing, professional services, and more. Workflows show every step the AI takes, with RBAC, SSO, and audit logs covering each Agent and Workflow. ChatGPT Enterprise and Claude Enterprise offer solid admin controls and suit individual productivity, while Cassidy adds Workflows that give every employee the same result.
Which of these platforms lets you choose a different AI model for each task?
Cassidy lets builders choose Claude, OpenAI, Gemini, or open source models for each Agent or Workflow step, and switch without rebuilding. ChatGPT Enterprise runs only on OpenAI's models, and Claude Enterprise runs only on Anthropic's. Teams that like both get both in one place, and can move to the best new model as each vendor releases one. OpenAI or Anthropic may also ship new features before Cassidy does, though Cassidy's arrive enterprise ready, with governance in mind.
Can we move our existing agents and prompts from ChatGPT Enterprise or Claude Enterprise to Cassidy?
Yes, and it is quick. Prompts and agent instructions can be copied out of ChatGPT Enterprise or Claude Enterprise and recreated in Cassidy, and describing the process in plain language is often enough to rebuild it as an Agent or Workflow. Cassidy's solutions team has experience doing this and helps with the first set, so seats can keep running alongside until you are ready.
Which platform is best for a first enterprise-wide AI rollout: ChatGPT Enterprise, Claude Enterprise, or Cassidy?
Cassidy. It is the easiest to scale and manage, and you can prompt your way to a working Workflow with our team helping you get it right. Teams can start with the chat experience and models they know, then add auditable Workflows on the same platform. ChatGPT Enterprise and Claude Enterprise work for quick, simple chat, but scaling past that ties teams to a single model vendor.
Do ChatGPT Enterprise, Claude Enterprise, or Cassidy train AI models on company data?
None of the three trains on company data by default. OpenAI does not use ChatGPT Enterprise inputs or outputs for training by default unless a customer opts in. Anthropic does not train on inputs or outputs from commercial products like Claude Enterprise by default, except thumbs up or down feedback, which admins can turn off. Cassidy never uses customer data to train models, and it is SOC 2 Type II attested, GDPR compliant, HIPAA compliant, and CASA validated.
