Most mid-sized employers treat a cloud migration as a technology project with a technology budget. The projects that run late or over cost usually have something else in common: nobody planned who would do the work, who would run it afterward, and who would pay for the gap in between.
This is a look at the four pressure points we see most often and the hiring decisions behind each one.
1. Legacy systems need people who know both sides
Older systems rarely move cleanly. Data formats differ, custom integrations break, and workflows that grew up around on-premises tools have to be rebuilt rather than copied.
The person who understands why the old system behaves the way it does is often a long-tenured employee who is not a cloud specialist. The person who knows the target platform has never seen your data. Neither can finish the job alone.
What to do:
- Name the internal owner of each legacy system before the project starts.
- Pair that person with a cloud engineer or data engineer for the full length of the migration, not just the kickoff.
- Document the workarounds. Every legacy system has them, and they are the first thing lost in a move.
2. Costs rise after go-live, not before
The migration budget is usually reasonable. The run-rate afterward is where owners and controllers get surprised. Usage-based pricing means a busy month costs more than a quiet one, and an application that makes more calls than planned can push a bill well past forecast.
Scope also grows. A company that moves its CRM and likes the result will want to move finance, reporting and operations next. Each step is sensible, and together they are a different project from the one that was approved.
For finance leaders, three habits help:
- Budget for the cloud environment as an ongoing operating line with an owner, not a one-time capital event.
- Assign someone to review usage and spend every month. That is a real part of a job, not a favour.
- Put a stage gate between phases so added scope gets its own approval and its own numbers.
This is also where the AI and data hires matter. Teams that want analytics or machine learning on top of cloud data tend to underestimate both the compute cost and the cleanup work needed first.
3. The skills gap shows up in your existing team
Your network administrator, your database lead and your ERP analyst already know your business. After a migration, their tools change. Some adapt quickly. Others lose months of productivity, and a few get frustrated enough to leave.
Training is the obvious answer, but it takes time that a busy team does not have. Operations leaders should plan for a dip in output during the changeover and decide in advance how it will be covered.
You have three realistic options:
| Option | Best when | Watch for |
|---|---|---|
| Train current staff | The team is stable and the platform is well documented | Slow progress while they keep up daily work |
| Hire permanent specialists | The cloud environment will be core for years | Long searches in a tight market |
| Bring in contract talent | The project has a clear end date | Knowledge leaving when the contract does |
Most employers end up with a mix. Contract specialists carry the build, current staff learn alongside them, and one or two permanent hires take over the run.
4. Plan the handover on day one
The weakest point in many migrations is the end. A contractor or consulting team finishes, the environment goes live, and the people left behind have never touched the hard parts.
Build the handover into the plan:
- Require written runbooks and recorded walk-throughs as deliverables.
- Have your own staff do part of the work, supervised, before the project closes.
- Decide who is on call, who approves changes and who owns security before launch, not after the first incident.
- Keep a short overlap period where the outside team is still reachable.
Hiring for a migration in Canada and the US
Cloud, security and data engineering skills are in demand on both sides of the border, and the best candidates are rarely looking. A search that starts after the project is already behind will cost you weeks you do not have. Start the role definition early, be specific about which platform and which stage of the work, and decide up front whether the role is contract or permanent.
A role described as general IT support will attract the wrong people. A role described as owning the cut-over of three named systems in nine months will attract the right ones.
What to do next
Before approving a migration, write down four things: who owns each legacy system, who owns the monthly cloud bill, which skills you will train versus hire, and who runs the environment after the project team leaves. If any of those is blank, that is your first hire or your first contract.
A Traverse recruiter can help you work out the mix of contract and permanent roles and find the people to fill them.