Wolf&Grayson EditorialCloud is not a destination; it is a journey. It is a long-term business redesign that must start with a clear purpose, anticipate organizational and financial implications, and invest in people, governance and realistic multi-year planning to succeed.
“There is no one size fits all. Before you say ‘we are going to do a cloud migration,’ you need to understand your why,” says Rose Hecksher Schamberger, a global technology executive and fractional CTO. She has led large-scale cloud programs across North America, Europe, Asia and Latin America, guiding enterprises and early stage companies through high-stakes migrations on both AWS and Azure. She shares the core principles that she believes every organization must consider when approaching cloud transformation.
Start With The “Why,” Then Design The Roadmap Beyond Day One
Schamberger’s first principle is simple: no architecture decision should be made without a clear business rationale. Security gaps in aging on-prem environments, the need for managed infrastructure, ambitions around resilience and scale on AWS or Azure, any of these can be valid drivers. The mistake, she argues, is treating the cloud move as a goal in itself.
“Understand your why,” she says. “Understand what would be the best, not exactly during the migration, but long term, and then create a roadmap that goes at least two or three years ahead.” That roadmap must look beyond cutover dates and sprint plans. It needs to anticipate how team structures will change, what skills will be required, how incident management will evolve, and how costs will behave as usage grows.
She describes the start of a migration not as an ending, but a beginning. Once workloads land in AWS or Azure, new capabilities become available, and so do new risks. The real value is created in the years that follow, as organizations modernize architectures, refine their use of managed services and continuously tune for performance, cost and reliability.
Cloud Transformation Is A Company-Wide Puzzle, Not A Pure Tech Project
Many executives still frame cloud transformation as an engineering challenge. Schamberger prefers a different metaphor. “It is a puzzle,” she says. “You have your puzzle sitting on a table and now you are moving this puzzle to the next table. You have to be careful because pieces can fall off.”
The “pieces” she refers to are not just services and databases. They include customer support workflows, escalation paths, sales commitments, access models, compliance reviews and vendor contracts. In a SaaS or ecommerce business, for example, support teams may rely on specific tools or network paths to access customer environments. Those assumptions can break during a move to AWS or Azure unless they are mapped deliberately.
She urges leaders to trace the end-to-end flow, from first customer contact to day-to-day operations, and to ask hard questions. If an incident occurs after the migration, who owns what? How will reliability targets be negotiated and enforced? What needs to change in customer support, DevOps, security, tech ops and finance so the organization functions as a single ecosystem rather than a series of handoffs?
“Yes, there is the technical part,” Schamberger says. “But you have to look at the end-to-end operations of your company to understand every single part that is going to be impacted, positive or negative, and make sure you adjust.”
Non-Negotiables: Cost, Governance And Cloud-Native Skills
When asked for her non negotiable principles for AWS and Azure transformations, Schamberger outlines four core pillars:
- Cost Optimization Comes First
Moving from on-premise infrastructure to the cloud usually increases costs, because you’re switching from capital expenses (capex) to operational expenses (opex), and many companies are surprised by this. While cloud offers major benefits, it rarely reduces costs. Schamberger stresses the need to model spend early, involve finance, understand pricing mechanics and align teams around the reality that security, reliability and scale are the true drivers of transformation. - Governance Across Every Touchpoint
Governance must extend far beyond engineering. “Do not think this is a product development issue that engineering will take care of,” she says. Every function that interacts with the product, from sales to support to security, needs clarity on new responsibilities and guardrails in a cloud environment. - Investing in Cloud-Native Talent
Schamberger calls talent readiness essential. Cloud native work on AWS or Azure demands new processes and patterns. “Make sure your engineering team is trained for cloud native development,” she says, emphasizing equal investment in operations training to ensure teams can support and troubleshoot effectively. - Bring in Expertise When Needed
She encourages companies to seek external guidance when facing large transformations. Fractional CTOs or cloud specialists can assess architectures and design realistic multi-year plans. “Things get worse before they get better,” and experienced support keeps teams focused on long term outcomes rather than early turbulence.
AI, FinOps And The Next Chapter Of Cloud Architecture
Looking ahead five to ten years, Schamberger sees AI and disciplined financial operations as permanent features of cloud architecture. “AI is not a trend anymore, it is a reality,” she says, but she is quick to add that many applications are not yet ready to leverage cloud AI services effectively. Compute and query costs on AWS, Azure or GCP can rise quickly if architectures are not carefully designed.
She views FinOps as “a necessity” because cloud costs are inherently more variable than traditional on-prem models. Provider choice, tech stack, licensing and data strategy all influence spend, whether a company opts for hot, on demand data or cheaper, less available storage tiers. For Schamberger, the role of a modern cloud architect is increasingly about balancing these forces: reliability and speed on one side, AI-driven innovation on another, and financial sustainability running through the middle.
She also points to reliability and deployment practices as underused advantages of AWS and Azure. Cloud infrastructure enables redundancy, controlled rollouts and rapid rollback that are difficult to match in fixed on-prem environments. When organizations design for their true peaks and lows, automate deployment pipelines and treat experiments as reversible, they reduce risk for both internal teams and customers.
Architecture Anchored in Reality
Across all of this, Schamberger returns to the same core belief: the architecture only works if it is anchored in business reality and human capability. As she puts it, “It is never all or nothing. You have to understand the big picture after you move.” The cloud can provide extraordinary tools, but it cannot replace clear thinking about why the transformation exists in the first place, who it serves, and how the organization will run once the move is complete.
For more insights from Rose Hecksher Schamberger on cloud, AI and scaling technology teams, connect with her on LinkedIn or visit her website.
