Outreach
AI Meeting Booking Agent
Converts interested replies into booked meetings on reps' calendars.
Outreach
AI Appointment Setter for Outlook Calendar
Inbound leads are qualified in conversation and booked into the Outlook calendars your reps already run their week from.
Reps who run their week from Outlook need qualified meetings to appear there, not in a separate tool. This edition qualifies leads over chat or email and books the ones who pass into Outlook Calendar through a native two-way Microsoft Graph connection. It reads live free and busy time, updates events when plans change, and writes every outcome to your CRM.
- Qualified leads booked straight into reps' Outlook calendars
- Live free and busy time checked through Microsoft Graph
- Every booking and outcome written back to your CRM
$4,400
20–30 working days
Optional maintenance $249/mo
What it is
AI Appointment Setter for Outlook Calendar qualifies leads over chat or email and books the ones who pass into Outlook Calendar, using a native two-way Microsoft Graph connection that reads and updates availability and events. Every booking and outcome is written back to your CRM. Bookings respect your working hours.
Why businesses buy it
For teams on Microsoft 365, every extra scheduling tool is another login and another place for meetings to go wrong. Manual qualification also slows the response to leads who are ready now. This edition qualifies and books inside the Outlook calendars your reps already trust, so the pipeline fills with real conversations rather than admin. The written scope covers the Graph permission and field mapping, one more connected system and the workflows before you order, so your IT team can approve the access with confidence.
Problems this solves
Leads are offered times that clash with reps' Outlook commitments
A two-way Microsoft Graph connection reads availability and events in Outlook Calendar before any slot is offered. Bookings also respect the working hours you set for each rep.
Unqualified leads take up space in reps' Outlook calendars
Leads answer your qualifying questions on chat or email first. Only those who pass are booked, so reps keep their calendar for conversations with real potential.
Booking outcomes never make it back to the CRM
Every booking and its outcome is written back to your CRM. Pipeline reports then include every meeting arranged by the setter, without reps re-entering anything by hand.
A good fit if
Your sales team runs on Microsoft 365, and every rep's week is planned in Outlook Calendar.
Leads that pass qualification still wait for a rep to propose times by email, and some go cold before a slot is agreed.
Your IT team can grant the Microsoft Graph calendar permission and give 30 minutes to a setup call.
You want each Outlook booking tied to the lead's CRM record, with the reason they qualified noted for the rep.
Not the right fit if
Your reps book in Google Calendar. See AI Appointment Setter for Google Calendar.
One leader needs their own inbox triaged and calendar managed, rather than a team booking leads. See AI Executive Assistant.
You send leads a Cal.com booking page and want its event types respected. See AI Appointment Setter for Cal.com.
You want broader conversational selling that handles objections and moves deals toward close. See AI Sales Agent.
How it works
- Your IT team grants the Microsoft Graph calendar permission, and a 30-minute setup call with your Outlook Calendar admin fixes which reps' calendars are in scope.
- We write down the field mapping: whose Outlook availability is read, what an event created by the setter contains, and how it links to the CRM.
- Leads arrive on the one channel in scope, chat or email; the setter checks the CRM for stage, owner and history, then runs your qualifying questions.
- Qualified leads are offered times drawn from the assigned rep's Outlook availability, and the event is written to that calendar when the lead accepts.
- Borderline answers, or requests outside your booking rules, are held for a person rather than booked automatically.
- Before launch, 50 documented scenarios run on sandbox or test records, covering double-booked reps, out-of-hours requests and disqualified leads.
What you provide within 72 hours
Your portal lists these the moment you order. Delivery starts the working day after everything is in and your access is checked.
- The Microsoft Graph calendar permission, granted by your IT or Microsoft 365 admin.
- An Outlook Calendar admin for a 30-minute setup call on the calendars in scope and the field mapping.
- Your ideal customer profile and qualification criteria, including what rules a lead out.
- Your sales playbook or sample emails, and ten real lead conversations.
- Access to the CRM or other single system you want connected.
- Booking rules, routing by rep, and one decision-maker.
- An API key for your own AI model account (for example OpenAI or Google Gemini), created for this build with a spending limit.
The 72-hour rule. Send everything on your checklist, including access, within 72 hours of ordering so your build starts on time.
Timeline
Start
Graph permission granted, setup call done, calendars and mapping agreed.
Weeks 1–2
Qualification flow and booking logic built from your criteria and conversations.
Week 3
Outlook Calendar and CRM connected; event writing checked on test records.
Weeks 3–4
50 documented scenarios run, covering clashes, out-of-hours requests and disqualified leads.
Week 4
Your review and two rounds of changes.
Go-live
Go-live, recorded handoff, field mapping handed over, 30 days of support.
| Option | Delivery time | Price |
|---|---|---|
| Standard | 20–30 working days | $4,400 |
| Express | 15–25 working days | $5,150 |
| Rush | 10–20 working days | $5,950 |
What you receive at handover
- The setter configured with a two-way Outlook Calendar connection and your CRM
- A documented field mapping for Outlook events and CRM records
- Microsoft access granted through user invites or keys you control
- A test report run on sandbox or test records
- An admin guide and recording of the 60-minute handoff session
- 30 days of post-launch support
Expected benefits and how to measure them
- Can fill reps' Outlook calendars with better-qualified meetings.
- Makes booking outcomes visible in the CRM without extra admin.
- Meetings that reps rate as qualified
- Add a simple fit field in the CRM and compare the share of good-fit meetings before and after launch.
- Bookings outside working hours
- Check Outlook for sales meetings booked outside set hours, for a month before and a month after.
- Outcomes recorded in the CRM
- Compare Outlook sales meetings with meetings that have an outcome logged in the CRM, for the same month.
Before you start: Note last month's booked meetings, how many reps felt were a poor fit, and how many outcomes reached the CRM.
These are things to track, not promised results. Outcomes depend on your data, your team and your market.
Running costs
The build price is one-time. AI model usage and hosting then cost roughly $50 to $250 a month in your own accounts, plus your existing CRM plan, and conversation volume sets where you land. Microsoft 365 and Outlook licenses are not part of this build.
AI usage while we build and test is billed to your accounts too.
Ask about running costsCustom requirements
If you need custom Outlook objects beyond the mapping, a third system, or more than six workflows, add a note at checkout. A written Change Quote arrives, and nothing extra starts until you accept it. Larger or bespoke projects go through the Custom AI request form.
Request a custom versionKeep it running
We recommend monthly maintenance: monitoring, fixes and a monthly allowance of change hours, for things such as bringing a new rep's Outlook calendar into scope or adjusting qualifying questions. It starts after the 30 days of support.
$249/mo (the minimum fee, includes 2 change hours)
Optional. Starts after the post-launch support period. Cancel any month.
How maintenance worksHow this compares
| Do it yourself with a SaaS tool | Hire a custom agency | Upmark Labs | |
|---|---|---|---|
| Price | A booking add-on charges per user, every month | A Microsoft developer quotes the Graph work separately | Ours is one fixed price, shown before you buy |
| Who gets booked | Anyone who opens the link | Depends on the brief | Ours books only leads that meet your criteria |
| CRM record | Often a separate list to reconcile | Depends on the integration scope | Ours writes the booking and outcome to the CRM |
| Delivery | A link is quick to share | Usually several weeks | Ours has a fixed delivery time shown before you buy, with faster options |
Questions about this product
What permission does the Outlook Calendar edition need?
The Microsoft Graph calendar permission, granted by your IT or Microsoft 365 admin, plus that admin for a 30-minute setup call. The permission decides which calendars the setter can read and write, so the field mapping is agreed on that call before any build work starts.
Does the setter see what is inside reps' Outlook meetings?
It reads availability and events within the Graph calendar permission and the agreed field mapping, which is what it needs to find free time and avoid clashes. The mapping records exactly which calendars and event details are in scope, and anything outside it is not read.
Can leads be booked with different reps in Outlook?
Yes. Your routing rules pick the rep, for example by territory, segment or existing account owner, and the setter books into that rep's Outlook calendar. Every rep you want included must be named in the field mapping during intake so their calendar is in scope.
What does the Outlook setter write back to the CRM?
The qualification outcome, the answers that decided it, and the booking itself, written to the lead's record in the one additional system you connect, usually your CRM. Disqualified leads are logged with the reason too, so reps can see why a meeting exists and why others do not.
How long does the Outlook Calendar edition take to deliver?
The standard delivery time is fixed and shown next to this page, with express and rush options if you need it live sooner. The clock starts once the Graph permission, the setup call and your playbook are complete. Choosing a faster option changes the delivery date only, not what is built.
What are the monthly costs on top of Microsoft 365?
Roughly $50 to $250 a month in your own accounts for AI model usage and hosting, plus your current CRM plan. Microsoft 365 and Outlook stay on your existing licenses. Monthly maintenance is optional, for ongoing changes. It covers monitoring, fixes and change hours, such as bringing a new rep's Outlook calendar into scope or adjusting qualifying questions.
Turn qualified replies into Outlook meetings without the email chain.
Order AI Appointment Setter for Outlook Calendar and qualified leads become Outlook meetings with the right rep, without the email chain.
Works well with
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