I’ve talked to so many people—team leads, managers( even from some of the top product companies who are willing to pay higher than industry average), and even startup/unicorn founders—and there’s one complaint I hear over and over: it’s really hard to hire good DevOps people. They’re always saying things like, “It’s so tough to find someone with the right depth of skills.” What’s your take on this? Why do you think hiring DevOps experts is such a challenge? Have you faced the same issue in your own experience?

Edit 1: I agree while there are some who want to underpay and ask the sky, this cohort also includes a folks from some of the top product companies who work with as part of my corporate workshops. The complaint is more of n the lines of depth of skills. Their say is people put 15 different skills in their resume, have certifications as well, but seem to have surface level knowledge. I have rephrased the original question accordingly.

Edit 2 :

I am not a recruiter. I am a corporate trainer, specialised in Devops , and ofcourse a self made Devops guy who started with his Linux/ops/tech ops career even before devops as a word was born. . The reason why I ask this is to provoke both sides, companies who want to hire but struggling ( not because of cost reasons, people who want to underpay for someone who is adding lot of value, let them suffer, and rot them in hell… ) and techies who want to make a career in devops and struggling to think about the root cause and the real problems, and come up with solutions, together.

I manage a mature SaaS product and I’ve ended up as the accidental DevOps person after replacing an offshore team that didn’t really have the role covered. I’m technical, but not at the level I need for where we’re headed, so it’s time to bring in someone who genuinely knows the space. Ideally on a contract to tackle the big projects , then hopefully keep them on part-time afterward for ongoing support.

This isn’t a job post (I’ll share that to r/devopsjobs soon), but I’m looking for advice from people here who’ve been on either side of this. If you want to DM with thoughts or recommendations, my inbox is open.

The main projects are things like finishing our Jenkins to ArgoCD migration, stabilizing the dev environment, upgrading Kubernetes and keycloak, fixing Terraform drift, and tightening up security by swapping bastion for SSM. Down the line we’ll need a coordinated Postgres upgrade and help implementing something like Flyway. I have a rough roadmap with phases, but I also want the person I hire to shape it once they’ve seen the guts.

Where I could use your help is figuring out the right approach.

First, what’s a sane way to interview and evaluate someone who’s supposed to outclass you? I'm thinking of one focused technical conversation to hear their high-level plan for the Jenkins migration, and then maybe a short, paid working session in a non-prod environment to see how they think. Is that a good signal, or is there a better way to assess real-world skills?

Second, where do you actually find great freelance talent these days beyond the job subreddits? Are places like Upwork, boutique agencies or certain communities worth cutting through the noise for?

Third, what's a safe but effective way to handle day one access? My instinct is to start with more limited permissions and expand as we build trust, but I don’t want to slow them down. How do you prefer to start when you join a new project?

Finally, I have a roadmap, but I want the person I hire to have ownership and help shape it. I want someone who’ll call out gaps in my plan, not just follow checklists. For the contractors here, what are the green flags that tell you a client will actually listen to your expertise, and what are the red flags that tell you to run?

Budget isn’t FAANG, but it’s sane. I care more about working with someone who’s proactive, communicates clearly, and leaves things tidier than they found them. If you’re interested, keep an eye out for the official post, but I’d really appreciate any advice on process, places to look, or things I might not know enough to ask yet. Thanks.

Is there any 90 Days DevOps Challenge to improve oneself in DevOps technologies?