Key takeaways
- Outlook teams file mail with categories, folders and rules, so test a CRM on your real mailbox, not a demo inbox.
- Your Microsoft 365 admin may need to approve a third-party app before anyone connects it, so ask what access each tool requests.
- Calendar and chat matter as much as mail: check Outlook calendar and Microsoft Teams support separately.
- Pebbles Ai suits Outlook users who want assistant help in the inbox; its calendar connection is Google Calendar and it has no Teams connection.
What an Outlook CRM has to get right
An Outlook CRM has to fit the way a Microsoft shop already handles mail, because those teams sort with categories, folders and rules rather than Gmail labels and filters. A tool built Gmail first can still work, but the gaps show up in the small habits your reps rely on every day.
The other difference is governance. In many Microsoft 365 tenants an administrator approves which apps may read mailboxes, so the CRM you choose has to pass that review before a single rep can connect.
- Mailbox access: does each person connect their own Outlook inbox, and can one person connect more than one?
- Filing: does the tool respect Outlook categories and rules, or does it expect labels?
- Contacts: can you import contacts directly from Microsoft, or only through a CSV export?
- Calendar: does it read Outlook calendars, or only Google Calendar?
- Evidence: can the vendor show a Microsoft 365 App Compliance Program result or other security documentation your admin will accept?
How the main CRMs suit a Microsoft 365 team
All five are complete CRMs, and the Outlook detail varies enough that you should confirm it on each vendor's own Microsoft integration page before a trial. The notes below cover what each product says it does on its own site.
- Salesforce Sales Cloud: an enterprise CRM with suites from Starter to Max, forecasting and pipeline inspection, and Agentforce as an add-on; built for organisations that want a highly customisable CRM of record with admin control.
- HubSpot Sales Hub: free tools for up to two users, then paid seats with sequences, calling and forecasting, inside HubSpot's marketing and service platform.
- Pipedrive: a sales CRM organised around deal stages you move along a board, with automations and an AI email writer.
- Zoho CRM: a free edition for up to three users, and a Standard plan that lists email integration, mass emails, cadences and built-in calling; a natural fit if you already use other Zoho apps.
- Attio: a flexible, data-model-first CRM with automatic enrichment and email and calendar sync, plus a free tier for small teams.
Is there a CRM for Microsoft Teams users
Yes, but Microsoft Teams support is a separate question from Outlook support, so check it on its own. Teams users usually want deal updates and record links to land in the channels where they already talk, and that depends on whether the vendor publishes a Teams app and what it can post.
Look for the vendor's listing in the Teams app store rather than a logo on a features page, and ask whether the app only sends notifications or also lets people update records from a chat.
Where Pebbles Ai fits an Outlook team
Pebbles Ai fits Outlook users who want an assistant working inside the inbox they already have. Smartbox treats Gmail and Outlook at parity, so the assistant searches, reads, replies to and files Outlook mail with categories and rules, and more than one Outlook inbox can be connected per person.
Contacts import from Microsoft, Google or a CSV into the CRM, which is labelled Beta. If your records live in Attio or Pipedrive instead, the assistants read and update them through MCP from the chat, each write approved under the execution mode. Pebbles Ai holds Microsoft 365 Certification, which covers its Outlook connection.
When an Outlook team should look elsewhere
Look elsewhere if scheduling from the CRM against Outlook calendars is a must, because the Pebbles Ai calendar connection is Google Calendar. The same applies to chat: Pebbles Ai connects to Slack, not Microsoft Teams.
A team that needs forecasting, a finished non-beta CRM or a native Salesforce or HubSpot connection should keep one of the full CRMs above and judge Pebbles Ai as the assistant and inbox layer beside it.
The CRMs at a glance
Each product's category, whether its site lists a free plan, and the email features its own site names.
| Category | Free plan | Email features named on its site | |
|---|---|---|---|
| Salesforce Sales Cloud | Enterprise CRM | Yes | See their site |
| HubSpot Sales Hub | CRM platform with sales software | Yes | Sequences |
| Pipedrive | Pipeline-focused sales CRM | No | AI email writer |
| Zoho CRM | CRM platform | Yes | Email integration and mass emails |
| Attio | Modern data-driven CRM | Yes | Email and calendar sync |
| Pebbles Ai | Go-to-market workspace with a CRM labelled Beta | No | Smartbox for Outlook and Gmail, with Write with AI |
Entries summarise each vendor's own site when checked; confirm Outlook and Microsoft 365 details with the vendor. Pebbles Ai has no free plan; Pro and Team start with a 1-month free trial.
The products compared
Salesforce Sales Cloud
Enterprise CRM
The enterprise CRM platform for sales, with suites from small business to Max, forecasting and pipeline inspection, and Agentforce AI agents as an add-on or included at the top tier.
Best for: Organisations that need a highly customisable CRM of record with deep forecasting, admin control and an enterprise ecosystem.
Pricing model: Per user per month; Starter billed monthly or annually, higher suites billed annually. Source: Salesforce Sales Cloud pricing
Read the comparison with Salesforce Sales Cloud Visit Salesforce Sales Cloud

HubSpot Sales Hub
CRM platform with sales software
A CRM-centred sales suite with free tools, seat-based paid tiers, sequences, calling, forecasting, a prospecting agent and AI features, part of HubSpot's wider marketing and service platform.
Best for: Companies that want one mature CRM across marketing, sales and service, with the HubSpot Marketplace of apps and free tools for up to 2 users.
Pricing model: Free tools, then Starter, Professional and Enterprise priced per seat; onboarding fees on higher tiers. Source: HubSpot Sales Hub pricing
Read the comparison with HubSpot Sales Hub Visit HubSpot Sales Hub

Pipedrive
Pipeline-focused sales CRM
A sales CRM built around visual pipelines, with an AI sales assistant and email writer, automations, forecasting reports and add-ons for lead generation and campaigns.
Best for: Small companies and growing sales teams that track deals on a kanban board and want AI help and task automation without a long set-up.
Pricing model: Plans and prices are on their own pricing page. Source: Pipedrive pricing
Zoho CRM
CRM platform
A per-user CRM from Zoho with a free edition, sales automation, forecasting, cadences, built-in calling and the Zia AI assistant, part of a wider suite of Zoho business apps.
Best for: Small and mid-sized companies that want an affordable, configurable CRM with forecasting, calling and automation, especially if they already use other Zoho apps.
Pricing model: Free, Standard, Professional, Enterprise and Ultimate, per user per month, with a discount for yearly billing; CRM Plus is a separate bundle. Source: Zoho CRM pricing
Attio
Modern data-driven CRM
A flexible, data-model-first CRM with automatic enrichment, email and calendar sync, sequences and call intelligence on Pro, and a free tier.
Best for: Startups and scale-ups that want a customisable CRM with enrichment and a developer-friendly API.
Pricing model: Free, Plus, Pro and Enterprise, per user, with seat and workspace credits. Source: Attio pricing
We make Pebbles Ai. Facts about other products come from their own public pages, checked on .
Where Pebbles Ai fits
- CapabilitySmartboxSmartbox works in Outlook at parity with Gmail, using categories and rules, with Write with AI drafting replies from the thread, the recipients and your brand voice.
- CapabilityProspecting & customer recordsImport contacts from Microsoft, Google or a CSV into the Beta CRM, with custom fields, merge and saved views for deals and tasks.
- FoundationIntegrationsConnect more than one Outlook inbox per person in Settings, and add Attio or Pipedrive from the MCP catalogue, which may change.
Common questions
Does Pebbles Ai work with Outlook categories and rules?
Yes. The assistant uses Outlook categories and rules where Gmail uses labels and filters. In Outlook only sending is an approval action, and it follows the execution mode.
Can I bring my Outlook contacts into a CRM?
Most CRMs accept a CSV export from Outlook. Pebbles Ai also imports contacts directly from Microsoft or Google.
Does Microsoft 365 Certification make a CRM safe to use?
Not on its own. It shows an app has been through the Microsoft 365 App Compliance Program for the connection it covers. Pebbles Ai holds it for its Outlook connection; ask every vendor for its own evidence.
Do I have to stop using Outlook to adopt a CRM?
No. Every CRM here is used alongside a mailbox, and Pebbles Ai saves generated emails as drafts in your connected Outlook mailbox.
About this page. Written by the Pebbles Ai team for people who run sales, marketing and growth. Last updated .