/ Research
How Microsoft Copilot, Claude Enterprise, and Cassidy compare at a glance
| Strategic Goal | Microsoft Copilot | Claude Enterprise | Cassidy |
|---|---|---|---|
Primary philosophy and positioning | Microsoft 365-native AI chat with built-in agents and Cowork | 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 | Basic setup rides on Microsoft 365; heavier automation involves IT | 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 | Cowork, Copilot Studio, and Power Automate across separate systems | 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 and Anthropic, with no Google or Gemini models listed | Anthropic 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 | Projects scope files; enterprise search queries connected tools | Knowledge Base syncs continuously and grounds every Agent and Workflow Win |
Implementation support and onboarding | Microsoft documentation, FastTrack, and partner services | 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 Microsoft tutorials, templates, and partner 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 | Agent 365 extends Entra, Purview, and Defender across several consoles | 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 | Native in Microsoft 365, with automation tied to Microsoft's stack | Tied to Anthropic's models and roadmap | Model-neutral and system-neutral; easiest to scale and manage Win |
Consumer-style apps and extras | Polished Copilot app for personal everyday use | 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 anyone comfortable in Microsoft 365 apps | 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 centered in Microsoft 365 wanting in-app help for individual tasks | 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.
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
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, 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
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
- 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, with no Power Platform environment needed
- 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
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.
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
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
- 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
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.
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
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 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 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 Microsoft Copilot, 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
Microsoft Copilot if…
- Your team works mainly inside Microsoft 365 and needs help drafting, summarizing, and analyzing
- Native embedding in Word, Excel, Outlook, and Teams matters more than cross-system automation
- You have IT and Power Platform skills available to build heavier automation
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 needs an audit trail at every step
- You want one process to run the same way for every employee
- You want models chosen per step, including OpenAI, Claude, Gemini, and open source options
- You want the easiest rollout to scale and manage, and to prompt your way to a working Workflow with our team's help
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: Microsoft Copilot, 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. Microsoft Copilot 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: Microsoft Copilot, 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. Microsoft Copilot 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. Microsoft Copilot supports OpenAI and Anthropic across several surfaces, with availability varying by license and admin settings, and no Google or Gemini models in Microsoft's published lists. Claude Enterprise runs only on Anthropic's models. 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 Microsoft Copilot or Claude Enterprise to Cassidy?
Yes, and it is quick. Prompts and agent instructions can be copied out of Microsoft Copilot 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: Microsoft Copilot, 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. Microsoft Copilot and Claude Enterprise work for quick, simple chat, but scaling past that means more products and consoles, or a single model vendor.
Do Microsoft Copilot, Claude 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. 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.
