How to break into cloud careers when you're stuck in on-premises roles

My Top 3 Pieces of Advice

Jul 03, 2025

Hey, Prasad here 👋 I'm the voice behind the weekly newsletter "Big Tech Careers."

In this week's article, I provide my top three pieces of advice on how you can transition your career to cloud.

If you like the article, click the ❤️ icon. That helps me know you enjoy reading my content.

I do get a lot of LinkedIn DMs. I try and respond to as many as I can. But then there are a few LinkedIn messages which stand out because:

They provide proper context
They have done their due diligence
They have clear ask

One such DM is as follows:

Subject: Seeking Your Guidance on Cloud
Hi Prasad,

I hope you are doing well.

I always enjoy reading your articles and follow many individuals from the BeSA program. Currently, I am a Senior Infrastructure Solution Architect, having dedicated 10+ years to my organization. My experience primarily lies in On-Prem technologies, but I am very enthusiastic about cloud solutions. In 2020, I earned my AWS Solution Architect-Associate certification and Terraform certification out of personal interest. Unfortunately, due to the constraints of my role with On-Prem systems, I have not been able to apply these skills effectively in practice.

I am eager to transition into cloud opportunities but find my options limited within my organization. Although attending the BeSA program was encouraging and insightful, I still feel trapped in my current situation. To stay updated with technology trends, I subscribe to training providers like Pluralsight and read books such as "Solutions Architect's Handbook" along with various resources on cloud computing. However, it has become increasingly clear that it is time for me to explore new career paths specifically focused on cloud technologies.

What would be your top three pieces of advice for breaking through this cocoon and pursuing opportunities in the cloud sector? Your insights would be invaluable as I navigate this transition.

Best regards,
XXX

Here's my personalized advice to this person, shared publicly, to help any newsletter readers who find themselves in a similar position.

Here are my top three pieces of advice for breaking into cloud opportunities:

1. Create Visible Proof of Your Cloud Expertise

Since you can't demonstrate cloud skills in your current role, you need to create external evidence of your capabilities.

Start a cloud-focused blog or LinkedIn newsletter where you document hands-on projects, architectural decisions, and lessons learned.

Build real projects using AWS free tier resources - perhaps migrate a fictional on-premises application to the cloud, or create a multi-tier architecture that showcases your understanding of cloud-native patterns.

This visible portfolio will be crucial when speaking with potential employers who might otherwise overlook candidates without direct cloud experience.

The best example I can give you of someone doing this effectively is Janarthanan Ravikumar. Take a look at his LinkedIn profile, particularly the featured posts showcasing the hands-on projects he's been building and sharing publicly. These aren't your beginner projects like 'Launch an EC2 instance' or 'Create an S3 bucket' tutorials. He goes well beyond the basics.

Here are some of the projects he's completed:

What sets his work apart is how he presents these projects—complete with detailed architecture diagrams, AWS Management Console screenshots, and GitHub repositories containing code snippets and comprehensive step-by-step documentation.

2. Leverage Your On-Premises Experience as a Strategic Advantage

Don't view your 10+ years of on-premises experience as a limitation - it's actually a significant competitive advantage. Many organizations are in the middle of cloud migration journeys and desperately need architects who understand both worlds.

Position yourself as someone who can bridge the gap between legacy systems and cloud-native solutions. Depending on your background, skills and experience, focus your networking and job search on companies undergoing digital transformation rather than cloud-native startups.

Your ability to speak to the challenges of hybrid architectures, data migration strategies, and organizational change management makes you incredibly valuable to the right employer.

This approach works because you are not competing with cloud-native candidates on their turf - you are offering something they couldn't: deep understanding of the problems that cloud solutions are meant to solve. Companies value this perspective because most cloud migration projects fail not due to lack of cloud knowledge, but due to insufficient understanding of the existing systems being migrated.

3. Build Strategic Relationships Within the Cloud Community

Networking in the cloud space is fundamentally relationship-driven. Make it a priority to attend local AWS user groups, cloud meetups, and industry conferences—many offer virtual participation options that make them accessible regardless of location.

On LinkedIn, engage authentically with cloud architects and hiring managers. Share meaningful insights, contribute thoughtful comments to posts, and offer your unique perspective on cloud migration challenges. This isn't about self-promotion; it's about adding genuine value to conversations.

The AWS Community Builder program can be a game-changer for building relationships within the cloud community. I've witnessed many professionals launch successful cloud careers through this program. However, gaining acceptance isn't straightforward—you'll need to apply and stand out among thousands of applicants. Building visible proof of your cloud expertise and sharing your knowledge publicly will significantly strengthen your application.

You might view this as a chicken-and-egg dilemma: needing to create content to join the community builder program to unlock opportunities. Instead, think of it as a flywheel effect. Those who embrace this flywheel mindset are the ones who truly take off. I came across a LinkedIn post - it showcases how Brook Jamieson and Linda Haviv both started by learning AWS and sharing their journey publicly, stayed in touch using AWS Community Builders program, supporting each other along the way. Today, they're recognized cloud experts.

Seek out people who are on a similar journey within these cloud communities. Having companions on the path makes the entire experience more manageable and enjoyable.

Final thoughts

Breaking into cloud careers isn't just about technical certifications—it's about demonstrating your ability to solve real problems with cloud technologies. The combination of visible expertise, strategic positioning of your existing experience, and authentic relationship building creates a powerful foundation for career transformation.

Your transition timeline might be longer than you'd prefer, but your combination of existing experience and cloud certifications positions you well cloud roles rather than junior positions. Stay patient but persistent, and consider that the right opportunity might come from an unexpected direction.

Your journey from on-premises to cloud isn't a weakness to overcome; it's a unique strength that many organizations desperately need. The cloud industry values professionals who can bridge traditional infrastructure with modern cloud solutions, understand the complexities of migration, and guide organizations through digital transformation.

The path may seem challenging, but every cloud expert started where you are today. What sets successful career transitioners apart is their willingness to consistently create, share, and engage with the community while building genuine relationships along the way.

Have a specific career question or challenge you're navigating?

I regularly receive thoughtful messages like the one shared above, and I'm always happy to provide personalized guidance. Whether you're stuck in a similar situation, exploring a career pivot, or looking for strategic advice on breaking into cloud technologies, feel free to reach out with your specific context and clear questions.

The more detailed and specific your question, the more valuable advice I can share—not just for you, but for others in the community who might be facing similar challenges.

Big Tech Careers