/ Research
How Microsoft Copilot, ChatGPT Enterprise, and Cassidy compare at a glance
| Strategic Goal | Microsoft Copilot | ChatGPT Enterprise | Cassidy |
|---|---|---|---|
Primary philosophy and positioning | Microsoft 365-native AI chat with built-in agents and Cowork | One OpenAI workspace for employees' chat, Work, and Codex | Agents plus auditable Workflows for regulated, high-stakes work Win |
Time-to-value and implementation | Basic setup rides on Microsoft 365; heavier automation involves IT | Dedicated onboarding, with SSO and SCIM set in the admin console | Prompt your way to a working Workflow, with our team helping you get it right Win |
Multi-step workflows and event triggers | Cowork, Copilot Studio, and Power Automate across separate systems | Scheduled and event tasks for supported apps like Gmail, Slack, GitHub | CRM, meeting, form, and ticket triggers, with every step auditable Win |
Model choice and provider flexibility | OpenAI and Anthropic, with no Google or Gemini models listed | OpenAI models only | OpenAI, Anthropic, Google, and open source models, chosen per step Win |
Knowledge Base and company context | 100+ connectors for search; actions need plugins or Copilot Studio | Company Knowledge toggled per chat; admins control app access | Knowledge Base syncs continuously and grounds every Agent and Workflow Win |
Implementation support and onboarding | Microsoft documentation, FastTrack, and partner services | Dedicated onboarding and ongoing account management | Solutions team, hands-on training, and support after launch Draw |
Public tutorials, templates and community | Large public base of Microsoft tutorials, templates, and partner guides | Large public base of ChatGPT tutorials, templates, and third-party guides | Its own library and team support, with a smaller public base Lose |
Governance, permissions and audit logs | Agent 365 extends Entra, Purview, and Defender across several consoles | SSO, SCIM, RBAC, EKM, Compliance API, IP allowlisting | RBAC, SSO, and audit logs cover every Agent and Workflow run Draw |
Vendor lock-in and rollout at scale | Native in Microsoft 365, with automation tied to Microsoft's stack | Tied to OpenAI's models, roadmap, and workspace | Model-neutral and system-neutral; easiest to scale and manage Win |
Consumer-style apps and extras | Polished Copilot app for personal everyday use | Polished mobile and desktop apps, plus extras like voice | Focused on the team workspace, with fewer consumer-style extras Lose |
Everyday usability and learning curve | Familiar to anyone comfortable in Microsoft 365 apps | Familiar to employees who already know ChatGPT | Same chat and models, with a newer interface for most employees Lose |
Best fit: team size and use case depth | Teams centered in Microsoft 365 wanting in-app help for individual tasks | Teams wanting one familiar workspace for quick, simple chat and coding | 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.
Microsoft Copilot
- Copilot sits inside Word, Excel, PowerPoint, Outlook, Teams, and the Copilot app
- Drafting, summarizing, analysis, and search happen without leaving Microsoft 365
- Responses draw on the open file or thread plus work data, depending on surface and license
- Longer or cross-system tasks move to Cowork or Copilot Studio, which are separate products
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
Cassidy
- Agents run in Slack, Teams, Chrome, Word, Excel, PowerPoint, and Outlook
- Chat and Agents answer everyday questions on leading models, 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.
Microsoft Copilot
- Cowork supports scheduled and event-driven tasks, like matching emails or Teams messages
- Cross-system automation spans Copilot Studio, plugins, connectors, and Power Automate
- Heavier automation typically involves IT and Power Platform makers
- Controls for these agents sit across several consoles, including Entra, Purview, and Defender
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
Cassidy
- CRM changes, meetings, forms, tickets, and events from connected apps start Workflows
- One Workflow reads from one system and acts in another, including Teams and apps outside Microsoft like Notion or Confluence
- Business teams describe the process in plain language and build it, with IT setting guardrails
- 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.
Microsoft Copilot
- OpenAI and Anthropic power Copilot, with no Google or Gemini models in Microsoft's published lists
- A model selector appears in some experiences, with a real-time router by default
- Availability varies by surface, license, and admin settings, including regional Anthropic limits
- Copilot Studio adds further model options in some agent scenarios
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
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
- Different steps in one Workflow can run different models, matched to the task
/ Testimonial
Knowledge base, integrations, and deployment surfaces
How company context reaches the AI, and where employees actually use it.
Microsoft Copilot
- 100+ Copilot connectors and federated connectors bring in external content for search and grounding
- Connector content surfaces in Copilot Chat, Search, Excel, Researcher, and custom agents
- Write actions come through plugins, agents, and Copilot Studio, with setup varying by connector
- Native across Outlook, Teams, SharePoint, Word, Excel, and more
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
Cassidy
- Knowledge Base syncs continuously from Drive, SharePoint, Confluence, CRMs, and meeting transcripts
- Context applies automatically to every Agent and Workflow, with no per-chat toggle
- Source permissions carry through, and apps outside Microsoft, 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.
Microsoft Copilot
- Basic setup rides along with existing Microsoft 365 licensing and admin controls
- Cross-system agents can involve makers, admins, and Power Platform skills
- Rollout help comes from Microsoft documentation, FastTrack, and partner services
- Agent Builder suits simple agents, while Copilot Studio carries a separate learning curve
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
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.
Microsoft Copilot
- Agent 365 adds an agent registry with identity, security, and lifecycle controls
- It covers Microsoft-built, partner, and registered third-party agents
- Admins manage controls across Microsoft 365 admin center, Entra, Purview, and Defender
- Agent 365 is standalone or bundled in Microsoft 365 E7, with E5-class foundations for full coverage
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 limits
- Admins manage agents, spend, and plugins from a central console
- Enterprise adds EKM, IP allowlisting, and data residency in ten regions
Cassidy
- RBAC and SSO cover every Agent and Workflow, including each trigger, step, and approval
- 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 Microsoft Copilot is the better fit
Microsoft Copilot is the better fit for a team that lives mostly inside Microsoft 365 and needs help with individual tasks: drafting a document, summarizing an email thread, building a quick chart in Excel. Its native embedding across Word, Excel, Outlook, and Teams is a real advantage.
Teams usually outgrow it when automation has to cross systems, which can mean Copilot Studio, connectors, Power Automate, and IT support.
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.
/ Platform Recommendation
Choosing between Microsoft Copilot, ChatGPT Enterprise, and Cassidy
Match your situation to the lists below. If most of one list describes your work, that platform is the fit.
Choose
Microsoft Copilot if…
- Your primary, immediate problem is findability across a large, fragmented app ecosystem, and automation is a secondary concern
- Deep, breadth-first indexed search is your main use case, not multi-step process automation
Choose
ChatGPT Enterprise if…
- Your primary, immediate problem is findability across a large, fragmented app ecosystem, and automation is a secondary concern
- Deep, breadth-first indexed search is your main use case, not multi-step process automation
Choose
Cassidy if…
- Your team needs Agents and Workflows that finish high-stakes tasks end to end, beyond retrieving information
- You want explicit, reviewable control over every step an automation takes
- You want business teams to build and own automations themselves, without an API spec or admin-only setup
- Your automations need to reach Word, Excel, PowerPoint, and Outlook, not just chat and search
More enterprise AI platform comparisons
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: Microsoft Copilot, ChatGPT 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. Microsoft Copilot and ChatGPT 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: Microsoft Copilot, ChatGPT 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. Microsoft Copilot and ChatGPT 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 routes any Agent or Workflow step to OpenAI, Anthropic, Google, or open source models, and builders can switch without rebuilding. ChatGPT Enterprise runs only on OpenAI's models. Microsoft Copilot supports OpenAI and Anthropic across several surfaces, with availability varying by license and admin settings, and Microsoft's published model lists do not include Google or Gemini models. OpenAI 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 Microsoft Copilot or ChatGPT Enterprise to Cassidy?
Yes, and it is quick. Prompts and agent instructions can be copied out of Microsoft Copilot or ChatGPT 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: Microsoft Copilot, ChatGPT 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. Microsoft Copilot and ChatGPT Enterprise work for quick, simple chat, but scaling past that means more products and consoles, or a single model vendor.
Do Microsoft Copilot, ChatGPT Enterprise, or Cassidy train AI models on company data?
None of the three trains on company data by default. Microsoft says Copilot prompts, responses, and Microsoft Graph data are not used to train foundation models. OpenAI does not use ChatGPT Enterprise inputs or outputs for training by default unless a customer opts in. Cassidy never uses customer data to train models, and it is SOC 2 Type II attested, GDPR compliant, HIPAA compliant, and CASA validated.
