I’ve been in the tech game for a while now. I’ve seen companies rise and fall, and I’ve learned a thing or two about what it takes to build a successful startup. One of the most critical aspects of scaling a tech company is having the right tools in place. And when it comes to monitoring and observability, Datadog is a name that comes up a lot.
I’ve personally been involved in onboarding over 100 companies to Datadog, both as a founder and as an investor. I’ve seen the good, the bad, and the ugly. And I’m here to share some of my hard-won lessons with you.
So, if you’re thinking about using Datadog, or if you’re already using it and want to get the most out of it, this article is for you.
Here are 13 things I learned after onboarding 100+ companies to Datadog.
Don't Boil the Ocean
When you first start with Datadog, it’s tempting to try and monitor everything. I get it. The platform is incredibly powerful, and you want to take advantage of all its features. But trust me, that’s a recipe for disaster.
You’ll end up with a flood of data, a ton of noise, and a team that’s completely overwhelmed. Instead, start small. Identify a handful of the most critical metrics for your business—the ones that tell you if you're making money or losing users. Focus on those first. Once you have a rock-solid foundation, you can start to expand your monitoring footprint.
I remember one of my portfolio companies, a promising e-commerce startup, made this exact mistake. They were so excited about Datadog that they tried to monitor every single metric from day one. The result? They were drowning in alerts, and their engineers were spending all their time chasing down false positives. It wasn't until we convinced them to take a step back and focus on the essentials that they started to see the real value of the platform.
Your Tagging Strategy is Everything
I can’t stress this enough: a good tagging strategy is the foundation of a successful Datadog implementation. Without it, you’ll have a hard time filtering your data, creating meaningful dashboards, and setting up effective alerts.
Think about the different dimensions you want to slice and dice your data by. For example:
- Environment:
prod,staging,dev - Service:
web,api,db - Customer:
customer-id
The more consistent and granular your tagging, the more powerful your monitoring will be.
At RemoteTeam, we had a very strict tagging policy. Every metric had to be tagged with the service, the environment, and the cloud provider. It was a bit of a pain to set up initially, but it paid off in the long run. We were able to quickly identify issues, track performance over time, and make data-driven decisions about our infrastructure.
Dashboards are for Storytelling
A dashboard is not just a collection of charts and graphs. It’s a story. It should tell you what’s happening in your system, why it’s happening, and what you need to do about it.
When you’re creating a dashboard, think about the audience. Who is it for? What are they trying to accomplish? What information do they need to see at a glance? A dashboard for your executive team should look very different from a dashboard for your on-call engineers.
I’ve seen some truly terrible dashboards in my time. I’m talking about dashboards with hundreds of widgets, no clear organization, and a color scheme that would make your eyes bleed. Don’t be that person. Keep it simple, keep it focused, and tell a clear story.
Alerts Should be Actionable
An alert that isn’t actionable is just noise. It’s a distraction that takes your team’s attention away from the things that really matter. Every single alert you set up should be tied to a specific, concrete action that someone needs to take.
For example, instead of setting up an alert that says “CPU usage is high,” set up an alert that says “CPU usage is high on the web servers, and it’s affecting customer response times. You need to scale up the fleet.”
The more context you can provide in your alerts, the better. Include links to relevant dashboards, runbooks, and playbooks. Make it as easy as possible for your team to diagnose and resolve the issue.
Don't Forget About Logs
Metrics are great for telling you what’s happening in your system, but they don’t always tell you why. That’s where logs come in. Logs provide the rich context you need to understand the root cause of an issue.
Datadog’s log management capabilities are incredibly powerful. You can search, filter, and analyze your logs in real-time. You can also create metrics from your logs, which is a great way to get more visibility into your application’s performance.
One of the companies I invested in, a fintech startup, was struggling with a particularly nasty bug. They were seeing a spike in errors, but they couldn’t figure out why. It wasn’t until they started sending their application logs to Datadog that they were able to track down the problem. It turned out to be a race condition that was only triggered under very specific circumstances.
APM is a Revelation
If you’re running a modern, microservices-based application, you need to be using APM. There’s just no way around it. APM gives you end-to-end visibility into your application’s performance, from the front-end to the back-end.
You can see how long each transaction is taking, where the bottlenecks are, and which services are talking to each other. It’s like having an X-ray of your application.
I was working with a SaaS company that was having performance issues. Their customers were complaining about slow load times, but they couldn’t figure out where the problem was. We enabled Datadog APM, and within minutes, we were able to see that one of their downstream services was timing out. It was a simple fix, but it would have been impossible to find without APM.
Custom Metrics are Your Secret Weapon
Datadog comes with a ton of out-of-the-box integrations, but the real power of the platform comes from custom metrics. Custom metrics allow you to track the things that are unique to your business.
For example, you might want to track the number of new sign-ups, the amount of revenue you’re generating, or the number of items in your users’ shopping carts. These are the metrics that really matter to your business, and they’re the ones you should be focusing on.
At MovieLaLa, we had a custom metric that tracked the number of movie trailers that were being watched. It was a simple metric, but it was a great indicator of user engagement. We used it to make decisions about which trailers to promote and which ones to bury.
Anomaly Detection is Your Friend
As your system grows, it becomes harder and harder to set meaningful alert thresholds. What’s normal for a Tuesday morning might not be normal for a Saturday night. That’s where anomaly detection comes in.
Datadog’s anomaly detection algorithms can automatically learn the normal behavior of your system and alert you when something is out of the ordinary. It’s a great way to catch problems before they become critical.
I remember one time, we got an anomaly detection alert for one of our databases. The query latency was slightly elevated, but it was still within our normal threshold. We probably would have ignored it, but the anomaly detection algorithm flagged it as unusual. We investigated, and it turned out to be an early warning sign of a much bigger problem. We were able to fix it before it caused a major outage.
Don't Ignore Security
Datadog is not just for monitoring performance. It’s also a powerful security tool. You can use it to detect threats, investigate incidents, and monitor for compliance.
Datadog’s security monitoring features are still relatively new, but they’re already very impressive. You can collect security signals from all of your systems, from your cloud infrastructure to your applications. You can also create custom security rules to detect specific threats.
I was talking to a CISO at a large enterprise company, and he told me that Datadog had become an essential part of their security strategy. They were using it to monitor for everything from insider threats to zero-day exploits.
The Cost Can Add Up
Let's be real: Datadog is not a cheap platform. The cost can add up quickly, especially if you’re not careful. It’s important to have a good understanding of the pricing model and to keep a close eye on your usage.
There are a few things you can do to control your costs. First, be selective about the data you’re sending to Datadog. Don’t send everything. Second, use the right data retention policies. You don’t need to keep all of your data forever. Third, take advantage of Datadog’s cost management features. You can set up budgets, track your spending, and get recommendations on how to optimize your usage.
I’ve seen companies get hit with some pretty big bills from Datadog. It’s usually because they weren’t paying attention to their usage. Don’t let that happen to you.
The Learning Curve is Steep
Datadog is a powerful platform, but it’s not easy to master. The learning curve is steep, and it takes time to become proficient. Don’t expect to be an expert overnight.
Invest in training for your team. Datadog has a ton of great resources, including documentation, tutorials, and webinars. Take advantage of them. You should also consider getting certified. It’s a great way to validate your skills and show that you’re serious about mastering the platform.
I’ve seen a lot of companies struggle with Datadog because they didn’t invest in training. Their engineers were fumbling around, trying to figure out how to use the platform. It was a huge waste of time and money.
The Community is Amazing
One of the best things about Datadog is the community. There’s a huge community of users who are passionate about the platform and who are always willing to help. If you’re stuck, there’s a good chance that someone else has already solved the same problem.
The Datadog community is active on Slack, on the forums, and at meetups. Get involved. Ask questions. Share your knowledge. It’s a great way to learn and to connect with other people who are using the platform.
I’ve learned so much from the Datadog community over the years. I’ve gotten help with everything from setting up complex monitors to debugging tricky performance issues.
It's More Than Just a Tool
Datadog is more than just a tool. It’s a culture. It’s a way of thinking about monitoring and observability. It’s about being data-driven, proactive, and collaborative.
When you adopt Datadog, you’re not just buying a piece of software. You’re buying into a new way of working. You’re empowering your team to take ownership of their services, to make data-driven decisions, and to work together to solve problems.
I’ve seen it happen time and time again. When a company truly embraces Datadog, it transforms the way they work. They become more efficient, more reliable, and more innovative.
Final Thoughts
So there you have it. 13 things I learned after onboarding 100+ companies to Datadog. I hope you found these lessons helpful. Datadog is an incredibly powerful platform, but it’s not a silver bullet. It takes time, effort, and a willingness to learn to get the most out of it.
But if you’re willing to put in the work, the payoff is huge. You’ll have a more reliable, more performant, and more secure system. And you’ll be able to make better decisions about your business.
Now I want to hear from you. What have you learned from using Datadog? What are your biggest challenges? Let me know in the comments below.
Frequently Asked Questions
How were these items selected?
Each item on this list comes from direct experience, either from building my own companies or from patterns I've observed across the 200+ startups I've invested in. I prioritize practical, actionable items over theoretical concepts.
How do I know which items apply to my situation?
Start by honestly assessing where your biggest bottleneck is right now. The items that address that specific constraint will give you the highest return on your time and energy.
Are these recommendations still relevant in 2026?
Absolutely. While specific tools and tactics change, the underlying principles remain consistent. I update my thinking regularly based on what I'm seeing in the market and across my portfolio companies.
Which item on this list has the highest impact?
It depends on your stage and context, but in my experience, the items near the top of the list tend to have the broadest applicability. That said, sometimes the less obvious items create the biggest breakthroughs for specific situations.