Calendly VS Microsoft Outlook
As of 30 October 2026, Microsoft Outlook is named by 23,962 companies and Calendly by 114; Calendly skews to companies under 200 people (65% vs 41%), Microsoft Outlook to companies over 1,000 (26% vs 10%).
As of 30 October 2026 · refreshed daily · counts move as websites, DNS and career sites are re-read.
The website-and-DNS footprint is not comparable between a marketing suite and a CRM: Calendly's script and mail records show on hundreds of thousands of small sites, Microsoft Outlook rarely leaves a trace outside its own apps. Compare on the job-posting numbers; use the footprint for reach.
- Calendly: 2–200 employees
- 65%
- Microsoft Outlook: 2–200 employees
- 41%
- Calendly: 1,000+ employees
- 10%
- Microsoft Outlook: 1,000+ employees
- 26%
- Postings per company, 90 days
- 4.9 · 6.4
- Website or DNS footprint
- 83,363 · 0
Who chooses which
Share of each tool's companies in every segment. "Leans" marks a gap of more than two points.
| Segment | Calendly | share | Microsoft Outlook | share | Leans |
|---|---|---|---|---|---|
| Self-employed | 9 | 8% | 119 | 0% | Calendly |
| 2-10 employees | 18 | 16% | 1,333 | 6% | Calendly |
| 11-50 employees | 34 | 30% | 2,896 | 12% | Calendly |
| 51-200 employees | 22 | 19% | 5,672 | 24% | Microsoft Outlook |
| 201-500 employees | 14 | 12% | 4,722 | 20% | Microsoft Outlook |
| 501-1000 employees | 6 | 5% | 3,057 | 13% | Microsoft Outlook |
| 1001-5000 employees | 6 | 5% | 3,937 | 16% | Microsoft Outlook |
| 5001-10000 employees | 3 | 3% | 915 | 4% | even |
| 10,001+ employees | 2 | 2% | 1,311 | 5% | Microsoft Outlook |
| Segment | Calendly | share | Microsoft Outlook | share | Leans |
|---|---|---|---|---|---|
| Technology & software | 43 | 38% | 1,779 | 7% | Calendly |
| Business & finance services | 26 | 23% | 4,928 | 21% | Calendly |
| Consumer services & leisure | 18 | 16% | 1,061 | 4% | Calendly |
| Media & content | 8 | 7% | – | – | outside top 12 |
| Public, community & associations | 6 | 5% | 2,310 | 10% | Microsoft Outlook |
| Manufacturing & industry | 5 | 4% | 4,068 | 17% | Microsoft Outlook |
| Property & construction | 4 | 4% | 2,843 | 12% | Microsoft Outlook |
| Health care | 2 | 2% | 2,400 | 10% | Microsoft Outlook |
| Hospitality & travel | 2 | 2% | 514 | 2% | even |
| Commerce & trade | – | – | 1,341 | 6% | outside top 12 |
| Utilities & infrastructure | – | – | 811 | 3% | outside top 12 |
| Transport, logistics & rental | – | – | 763 | 3% | outside top 12 |
| Automotive | – | – | 588 | 2% | outside top 12 |
| Segment | Calendly | share | Microsoft Outlook | share | Leans |
|---|---|---|---|---|---|
| United States | 84 | 74% | 16,468 | 69% | Calendly |
| United Kingdom | 9 | 8% | 1,300 | 5% | Calendly |
| Germany | 5 | 4% | 1,892 | 8% | Microsoft Outlook |
| Canada | 4 | 4% | 1,217 | 5% | even |
| India | 3 | 3% | 156 | 1% | even |
| Brazil | 2 | 2% | – | – | outside top 12 |
| Poland | 2 | 2% | – | – | outside top 12 |
| Switzerland | 1 | 1% | 135 | 1% | even |
| Estonia | 1 | 1% | – | – | outside top 12 |
| France | 1 | 1% | 435 | 2% | even |
| Ireland | 1 | 1% | – | – | outside top 12 |
| South Africa | 1 | 1% | – | – | outside top 12 |
| Australia | – | – | 353 | 1% | outside top 12 |
| Netherlands | – | – | 242 | 1% | outside top 12 |
| Belgium | – | – | 138 | 1% | outside top 12 |
| Italy | – | – | 129 | 1% | outside top 12 |
| Austria | – | – | 127 | 1% | outside top 12 |
| Segment | Calendly | share | Microsoft Outlook | share | Leans |
|---|---|---|---|---|---|
| Marketing & communications | 300 | 46% | 5,223 | 3% | Calendly |
| Administration & office | 86 | 13% | 17,260 | 9% | Calendly |
| Sales | 80 | 12% | 14,074 | 7% | Calendly |
| Human resources | 23 | 4% | – | – | outside top 12 |
| Customer service & success | 17 | 3% | 6,542 | 3% | even |
| IT operations & business systems | 15 | 2% | – | – | outside top 12 |
| Software engineering | 15 | 2% | – | – | outside top 12 |
| Retail & store operations | 9 | 1% | – | – | outside top 12 |
| Business development & strategy | 7 | 1% | – | – | outside top 12 |
| Education & training | 7 | 1% | – | – | outside top 12 |
| Product, program & project management | 6 | 1% | 5,266 | 3% | even |
| Data & AI | 4 | 1% | – | – | outside top 12 |
| Healthcare clinical | – | – | 17,526 | 9% | outside top 12 |
| Finance & accounting | – | – | 12,728 | 6% | outside top 12 |
| Engineering (non-software) | – | – | 8,469 | 4% | outside top 12 |
| Skilled trades and field service | – | – | 8,169 | 4% | outside top 12 |
| Logistics warehouse and transport | – | – | 8,022 | 4% | outside top 12 |
| Construction and civil | – | – | 6,374 | 3% | outside top 12 |
| Quality, safety & environment | – | – | 5,833 | 3% | outside top 12 |
The companies behind each column
Companies using Calendly →
Companies using Microsoft Outlook →
Scheduling ranked →
Quote the sentence with the date and the link. The numbers change daily; the link always shows the current ones.
Microsoft Outlook is named by 23,962 companies in job postings and Calendly by 114; 28 name both. (Breaknorm, 30 October 2026, https://breaknorm.co/compare/calendly-vs-microsoft-outlook)
Read from the source, not self-reported
Every number on this page can be traced to a page we crawled or a posting we read. Full methodology →
- Job postingsRead hourly from career sites. A tool counts when the employer's own text names it as the team's system; both tools can count for one company.
- Website and DNSScripts and embeds on the company's pages, plus SPF, DKIM, MX and CNAME records of its domain that point at the vendor.
- SegmentsCountry, size and industry from the company profile built from its website.
- Not a reviewNo ratings, prices or feature claims. For those, read the vendors.
Calendly vs Microsoft Outlook: questions
Which is more used, Calendly or Microsoft Outlook?
By companies naming it in their own job postings, Microsoft Outlook (23,962) over Calendly (114). By website-and-DNS footprint, Calendly (83,363 vs 0), because its scripts and mail records sit on many small company sites.
Who chooses Calendly?
65% of Calendly companies have 2 to 200 employees, against 41% for Microsoft Outlook. 10% of Calendly companies have over 1,000 employees, against 26% for Microsoft Outlook.
Do companies run both?
28 companies name both in their postings, usually Calendly in marketing and Microsoft Outlook in sales, or during a migration.
Where do these numbers come from?
From the employer's own text in job postings read hourly from career sites, and from scripts found on company websites in our crawl. No vendor data, no surveys.
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