Managing Vendor Relationships in DevOps: Best Practices and Pitfalls

Three years ago, I was the guy fielding angry calls at 3 AM because our monitoring service decided to take a nap during Black Friday. Two years ago, I watched my team burn through a weekend trying to get our new deployment tool to actually deploy something. Last year, I spent six months in vendor hell because nobody bothered to read the fine print on our cloud storage contract.

Yeah, I’ve made every mistake in the book when it comes to vendor management. And frankly, most DevOps teams are making the same mistakes I did. So here’s what I wish someone had told me back then.

Your DevOps pipeline is basically a house of cards built on other people’s software. Think about it – you’re probably using AWS or Google Cloud, maybe Jenkins or GitHub Actions, Datadog or New Relic, Docker Hub, npm registry, and God knows what else. Each one of these is a potential point of failure.

The scary part? Most teams don’t even know how many vendors they’re dependent on until something breaks. Last month, I helped a startup count their vendor dependencies. They thought they had maybe 8-10 critical services. Turns out it was 23. Twenty-three different companies that could ruin their day if they decided to have problems.

When I first started engaging with vendors, I was far too polite as their customer. I’d listen to their sales presentation and, after an obligatory agreement nod, sign the contracts without enough focus on the hard questions I should have asked. Big mistake.

Now I’m that guy who asks uncomfortable questions in the first meeting. “What happens when your service goes down? How long does it actually take to get support? Can I get three customers using this in production for more than a year?”  If each of their answers includes some level of defensiveness, any avoidance, or attempt to give the pitch again instead of answering your questions – that is where your first red flag is.

Sales reps are nice, but they’re not going to help you at 2 AM when everything’s on fire. You need relationships with actual engineers and support people who understand your technical setup.

Here’s what I do now: after signing any contract, I ask for introductions to their technical team. I set up informal coffee chats with their engineers. I join their user communities. When problems happen (and they will), I’m not just ticket number 47891 – I’m “that guy from the coffee chat who asked smart questions about their API.”

Most SLAs are garbage. They’re written by lawyers to protect the vendor, not you. “99.9% uptime” sounds great until you realize it doesn’t cover the times when their service is technically up but performing so poorly that it’s unusable.

I learned this the hard way with a monitoring vendor. They were technically meeting their SLA while our alerts were taking 20 minutes to fire. Twenty minutes! By the time we got notified, half our users had already given up and gone home.

Now I write SLAs around what actually matters to my business. Response time for critical alerts. Time to acknowledge support tickets. Maximum downtime per incident. Real stuff that affects my team’s ability to do their job.

Two companies ago, we decided to go with a vendor that promised to handle everything – CI/CD, monitoring, security scanning, the works. The sales demo was gorgeous. The pricing looked reasonable. The integration was supposed to be seamless.

Six months later, we were spending more time fighting with their platform than actually shipping code. Their CI/CD was decent but their monitoring was terrible. Their security scanning flagged everything as a critical vulnerability, including a jQuery library that was three versions old.

We ended up ripping it all out and going back to best-of-breed tools. Cost us three months and a lot of credibility with upper management.

I once worked with a vendor whose support team seemed to exist in a parallel universe. Tickets would disappear into the void. Follow-ups would go ignored. When they followed up with me, it was with the “have you tried turning it off and on again?”.

The breaking point came during a production incident. Their service was down, our applications were failing, and their support team’s response was to close our ticket as “resolved” without actually fixing anything. I spent the next week migrating everything to their competitor.

Nothing ruins your day quite like opening a vendor bill and seeing a number that’s three times what you expected. This happened to me with a cloud storage vendor. Their pricing model was so complex that even their own sales team didn’t understand it properly.

Turns out we were getting charged for API calls, storage, bandwidth, and something called “metadata operations” that nobody had ever mentioned. By the time I caught it, we’d already blown through our quarterly budget.

I don’t care how good their marketing is or how many awards they’ve won. I want to see their service fail gracefully. I want to see how their support team handles problems. I want to know what happens when their engineers push a bug to production.

Here’s a trick I use: during the evaluation process, I deliberately try to break their service. I send malformed API requests. I try to exceed their rate limits. I simulate network failures. The vendors who handle this professionally and show me exactly what happens are the ones I want to work with.

I don’t just talk to their official reference customers. I dig around GitHub, Stack Overflow, and Twitter to see what people are actually saying about them. I look for patterns in complaints. I pay attention to how they respond to criticism.

One vendor I was evaluating had great official references, but I found a bunch of angry posts on Reddit about their billing practices. Guess what? Those Reddit users were right.

Before I sign any contract, I plan the breakup. I know that sounds pessimistic, but it’s saved my butt more times than I can count. I document how to extract our data, what the migration process would look like, and what the contract termination clauses are.

Having an exit strategy isn’t planning to fail – it’s planning to have options.

Vendor dashboards are pretty, but they don’t tell you what you need to know. I track metrics that directly impact my team’s ability to deliver software:

• How long does it take to deploy a change?
• How often do deployments fail because of vendor issues?
• How long does it take to get help when something breaks?
• What’s the real cost per deployment/user/transaction?

These are the numbers that matter. Everything else is just marketing fluff.

Here’s a metric most people ignore: is this vendor making my team’s life easier or harder? Are they reducing toil or creating it? Are they helping us ship faster or slowing us down?

I do informal surveys with my team every quarter. Simple questions: “Which vendors do you love working with? Which ones make you want to throw your laptop out the window?” The answers are usually more revealing than any performance dashboard.

The best vendor relationships I have feel like partnerships. We share roadmaps. We give each other feedback. We work together to solve problems. They want us to be successful. They want this for their own sake!

Of course, building this type of relationship doesn’t just happen. A relationship with a vendor takes ongoing work. It’s not just this communication over POC’s or how the product is working. This involves periodic technical conversations, ongoing feedback to be honest with them about what’s going okay, and not so great, as well as working together in collaboration on the tricky problems.

If something isn’t working, I tell the vendor exactly what the issue is, and what effect this has on our business. There are vendors that appreciate this honesty, and work with us to fix it. The bad ones get defensive or try to blame us.

I refer good vendors to other teams. I participate in their user communities. I provide feedback on their roadmaps. I speak at their conferences. When vendors see that I’m invested in their success, they’re more likely to be invested in mine.

Managing vendor relationships in DevOps isn’t about finding perfect tools or negotiating killer contracts. It’s about building a network of partners who help your team deliver software faster and with less stress.

The vendors you choose today will shape your capabilities for the next few years. Choose carefully, manage actively, and always keep your options open. Learn from my mistakes so you don’t have to make them yourself.

And remember – when a vendor relationship isn’t working, it’s usually not your fault. Don’t stick with bad vendors out of loyalty or sunk cost fallacy. Your team’s productivity and your own sanity are worth more than any contract.