I've touched every layer of the stack.
In 2019, I walked into TD Bank's Hosting Solutions group and learned what enterprise infrastructure really means. Not the whiteboard version—the 3 AM change windows, the RACI matrices that actually get followed, the vendor calls where Hitachi and Cisco are both pointing fingers and you're the one who has to make it work.
Over two years, I delivered 60+ infrastructure projects across TD's Direct Channel, Securities, and Wealth divisions. I managed the build and deployment of 400+ servers—physical iron and VMware Cloud. When COVID hit, I was part of the team that stood up the CRA forms and help finder systems that Canadians actually used.
That work taught me something important: Big 5 banks don't move slow because they're incompetent. They move deliberately because the cost of failure is enormous. When you're handling infrastructure that touches millions of Canadians' money, you earn your caution.
The Cloud Pivot
In 2022, I moved to TELUS Health and led something different—the first successful GCP migration for the Connecting Ontario healthcare platform.
Same regulatory intensity. Same stakeholder complexity. But now I was pulling systems out of data centres instead of building them in.
The skills transferred more than I expected. The governance muscle, the cross-team coordination, the ability to produce documentation that actually gets read by legal and security teams—all of that came from TD. What was new was learning to think in cloud-native terms: infrastructure as code, migration frameworks, operational readiness for systems that don't live on hardware you can touch.
The AI Layer
Most recently, through freelance consulting, I've been building what I think is the next evolution: AI-enabled PMO systems.
Not AI as a buzzword. AI as workflow automation that actually works:
- Prompt libraries that generate task briefs and acceptance criteria
- Automated risk flagging before humans even see the ticket
- Meeting summaries that write themselves
- Executive dashboards that update without manual data entry
The results? 23% faster cycle time. 35% reduction in meeting overhead. On-time delivery improvements that compound quarter over quarter.
What I've Learned
Looking back across TD, TELUS Health, and my freelance work, here's what I know now:
1. Governance isn't the enemy of speed—bad governance is.
The discipline I learned in Big 5 banking makes me faster in other environments, not slower. When you know how to navigate compliance, you stop fighting it and start designing around it.
2. The infrastructure-to-cloud journey is a people problem.
The technology is the easy part. The hard part is getting teams who've spent 15 years managing physical servers to trust systems they can't see.
3. AI won't replace PMs—but PMs who use AI will replace those who don't.
The automation I've built doesn't eliminate project management. It eliminates the drudgery that keeps good PMs from doing actual leadership work.
The Bridge Perspective
I've been on both sides of the infrastructure-to-cloud journey. At TD, I managed physical server builds and VMware deployments—the traditional infrastructure reality that still runs core banking. At TELUS Health, I led a first-of-kind GCP migration. Through freelance work, I've built AI-powered workflows that most enterprise PMs haven't caught up to yet.
Most organizations are somewhere on that journey. They're not fully legacy, but they're not cloud-native either. They're interested in AI, but they don't know where to start.
That's where I live now—helping teams bridge the gap between where they are and where they need to be.
What's Next
I'm looking for the next challenge—ideally somewhere in Canadian financial services or enterprise tech where I can bring all three layers together: the infrastructure discipline, the cloud migration experience, and the AI-enabled PMO practices that most organizations haven't adopted yet.
If you're building something interesting, let's talk.
Darshi Ajjamada is an AI-driven Project Manager with 10+ years of experience across banking, healthcare, and enterprise cloud programs. View full résumé or connect on LinkedIn.