Softwr

Remote Work · head to head

ConnectWise vs Datadog

C

ConnectWise

Remote Work

Software built to power your business

From
On request
Rated
-
Full reviewWebsite
Datadog logo

Datadog

Technology

Modern monitoring & security

From
$15/month
Rated
-
Full reviewWebsite

The short version

  • Each has a real cost: ConnectWise rMM, backup and cybersecurity products require filling out a quote request form rather than showing a price; only ScreenConnect remote support pricing is shown directly on the site, per connectwise.com, August 2026; Datadog consumption-based pricing model makes costs hard to predict and can scale quickly

Where they differ

Only the attributes on which ConnectWise and Datadog actually diverge.

Attributes where ConnectWise and Datadog differ
AttributeConnectWiseDatadog
Starting priceOn request$15/month
Pricing modelquoteUnknown
PlatformsWebWeb, Linux, Windows, macOS
CategoryRemote WorkTechnology
FoundedUnknown2010

Identical on both: free tier (No), user rating (Not yet rated).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in ConnectWise

Nothing recorded that Datadog does not also cover.

Only in Datadog

  • Infrastructure monitoring
  • Application performance monitoring
  • Log management
  • Real user monitoring
  • Synthetic monitoring
  • Security monitoring
  • Network monitoring
  • Serverless monitoring

What people use each for

The jobs each tool is most often brought in to do.

ConnectWise

No use cases recorded yet. See the ConnectWise review.

Datadog

  • Infrastructure monitoringnot ConnectWise
  • Application performancenot ConnectWise
  • Security monitoringnot ConnectWise
  • Log analysisnot ConnectWise
  • Cloud monitoringnot ConnectWise

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

ConnectWise

  • RMM, backup and cybersecurity products require filling out a quote request form rather than showing a price; only ScreenConnect remote support pricing is shown directly on the site, per connectwise.com, August 2026

Datadog

  • Consumption-based pricing model makes costs hard to predict and can scale quickly
  • Add-on modules significantly increase costs: custom metrics, indexed spans, extended retention
  • No free tier for production monitoring
  • High costs for organizations with large amounts of log data or high-cardinality metrics

Pricing, plan by plan

ConnectWise

On request

No published plan breakdown. See the ConnectWise review.

Datadog

$15/month
  • Infrastructure Monitoring$15/month
    • Host monitoring
    • Basic dashboards
  • APM$31/month
    • Application performance monitoring
    • Trace collection
  • Log Management$0.1/gb
    • Log indexing
    • Search and filter

Which should you pick?

Choose ConnectWise if

Nothing in the data separates ConnectWise from Datadog on the points above - pick on price and on how each one feels to use.

ConnectWise review

Choose Datadog if

  • You need infrastructure monitoring.
  • You work on Web, Linux, Windows, macOS.
  • You also want application performance monitoring.
Datadog review

Questions people ask

Is ConnectWise or Datadog better?
Neither clearly leads. ConnectWise starts at On request and Datadog at $15/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, ConnectWise or Datadog?
ConnectWise starts at On request and Datadog at $15/month.
Does ConnectWise or Datadog run on more platforms?
ConnectWise runs on Web. Datadog runs on Web, Linux, Windows, macOS.
What can ConnectWise do that Datadog cannot?
Datadog covers Infrastructure monitoring, Application performance monitoring, Log management, Real user monitoring.

Answered from the vendors’ own pages

Datadog: How is Datadog pricing structured?

Datadog uses consumption-based pricing tied to data volume ingested, hosts monitored, and products enabled. Infrastructure Monitoring starts at $15/host/month, APM at $31/host/month, and Log Management at $0.10/GB for indexed logs.

Source
Datadog: Does Datadog offer a free tier?

Datadog offers a free trial but not a permanent free tier for production monitoring. Pricing begins with paid plans only.

Source
Datadog: What integrations does Datadog support?

Datadog offers 1000+ built-in integrations including AWS, Kubernetes, Docker, Azure, GCP, and most major cloud platforms and services.

Source
Datadog: Can Datadog monitor Kubernetes clusters?

Yes. The Datadog Agent runs as a DaemonSet to provide real-time visibility into pods, nodes, deployments, and control-plane health across major Kubernetes distributions including EKS, AKS, GKE, OpenShift, and others.

Source
Datadog: How can I reduce Datadog costs?

Datadog bills based on indexed logs, custom metrics, and high-cardinality tags. Costs can be unpredictable and may run 2-3x estimates. Prepaying annually can secure 5-15% discounts.

Source
ShareXLinkedInRedditWhatsAppEmail

Related pages

More on ConnectWise

More on Datadog

Keep looking

Other head to heads