3. Is Now the Right Time?

2024-09-01

There’s a common belief among engineering teams that you shouldn’t migrate to AWS until your infrastructure is "mature enough." But in practice, the opposite is often true. Immaturity is a reason to migrate, not a reason to wait.

We’ve worked with many teams who lacked good CI/CD, had no good monitoring, and didn’t use containers or IaC. What happened after migration? The cloud forced them to mature. AWS acts as an accelerator for infrastructure discipline. It encourages automation, better separation of concerns, and clearer ownership models.

When You Shouldn’t Migrate

That said, there are valid reasons to delay a migration — but they rarely come from tech debt or team gaps. The real red flags are business-timing related:

You're weeks away from a major product launch
You’re in the middle of a critical sales cycle or fundraising event
Your product is stable, under no pressure, and not evolving
The business is declining or pivoting, and product direction is unclear

Migration during chaos compounds risk. You may still need to migrate, but the timing has to be surgical. Don’t try to replatform during your peak load season or while rewriting your frontend stack.

Signs You’re Overdue

In most cases, companies don’t migrate too early — they migrate too late. If you're seeing the following, you're probably already paying the price of delay:

Infra-related incidents are spiking
Developers are slowed down by provisioning or deployment issues
It's hard or expensive to hire infrastructure engineers
Developers are losing morale and confidence in the system
Too much spend on ops or third-party babysitting of infrastructure
You’ve recently raised funding and are expected to scale
You’re expanding into new regions and hitting infrastructure limitations
Usage is growing, but stability is dropping
Releases are blocked by infra constraints
Compliance is becoming urgent and your current system won’t pass

If you’re seeing any of these, your development process is bleeding. Delaying migration won’t stop the bleeding — it will just bury it deeper.

The Cost of Waiting

We’ve seen what happens when companies delay the decision too long:

Tech debt piles up, making the eventual migration harder
Critical infra knowledge stays siloed in a few senior engineers
Velocity continues to decline, making every sprint feel heavier
Production incidents increase, eroding customer trust
Developer frustration rises, and talent begins to churn
Ops teams burn out, and start making avoidable mistakes
Teams start building workarounds, entrenching poor patterns

One of the worst scenarios? A team builds multiple internal tools to "work around" infrastructure gaps, only to throw it all away six months later after the migration finally happens. You end up rewriting code and culture.

Good Timing for Migration

The best migrations happen during windows of strategic clarity — ideally when the team can breathe a little. Good moments include:

After a funding round, but before product pressure peaks
During a dedicated infra quarter or platform rewrite
Alongside product refactors or backend modularization
During a planned go-to-market pause (e.g., between product versions)
As part of a move into new markets or regions

What to avoid: doing it while rebranding, launching a new app, replacing your CRM, or onboarding half the company. Migrations need headspace.

How to Scope It Right

Once you commit, the trick is to scope smart. We never recommend migrating everything at once. Instead:

Start with one service or workload that’s easy to isolate
Pick something self-contained, with a clear outcome or user impact
Avoid stateful components (like databases) early on if possible
Run infra in parallel before cutting over fully
Use an “infra MVP”: minimal pipelines, observability, and IaC
Track internal wins and demo them to build buy-in
Tie phases to business milestones, not arbitrary timelines
Use standard infrastructure modules/templates to avoid decision paralysis
Train your team so they can manage and scale what you’ve migrated

In one client project, we began with just the background job runner — stateless, replaceable, low-risk. After success, the team migrated their API tier in weeks. What worked was not the tooling. It was the scoping and momentum.

What Readiness Really Means

Migration readiness isn't about your CI/CD maturity. It’s not about having perfect diagrams or hiring three platform engineers first. Readiness means:

You have a reason to move
Your product is evolving or scaling
Your team is open to change
Your business has headroom to focus

Most companies are more ready than they think. The key is not waiting for perfect conditions — it's about choosing the right entry point, scoping realistically, and committing with alignment.

If your product is moving forward, but your infra isn’t keeping up — that’s your signal. It’s time.