Eight lessons from eight years as a cloud product manager
"We need this feature to support enterprise customers," the sales engineer insisted during our weekly triage call. "A major competitor is threatening to take the deal."
I looked at the request: a complex networking feature that would take six months to build and serve exactly 12 customers. Meanwhile, our backlog had 47 developer experience improvements that could impact thousands of users daily. This was my third month as a cloud product manager, and I was about to learn the first of many expensive lessons about building products at cloud scale.
Eight years later, after managing products that serve millions of developers and handle trillions of requests monthly, I've learned that cloud product management is fundamentally different from traditional software product roles. The stakes are higher, the complexity is exponential, and the decisions you make today will either scale gracefully or become tomorrow's technical debt nightmare.
Here are the eight lessons that took me years to learn—and cost my teams countless hours when I got them wrong.
Lesson 1: Your biggest competitor is the status quo
Early in my cloud product career, I obsessed over feature parity with other major cloud providers. I'd spend hours analyzing their service catalogs, mapping our gaps, and prioritizing features based on competitive positioning. This approach felt logical but led us down a rabbit hole of me-too features that customers rarely adopted.
The breakthrough came when I started shadowing our solution architects during customer calls. I discovered that our real competition was customers' existing on-premises infrastructure and the "good enough" solutions they'd built internally.
Customers don't migrate to the cloud because you have the same features as competitors. They migrate when you solve problems their current setup can't handle, or when you make their lives dramatically easier. Focus on being 10x better at specific workflows rather than 10% better at everything.
What this means practically: Stop building features just because competitors have them. Instead, identify the workflows where customers are struggling with their current solutions and make those experiences magical.
Lesson 2: Scale breaks everything, including your assumptions
I learned this lesson the hard way when our compute service started experiencing mysterious performance degradation at high scale. Our architecture worked perfectly in testing with hundreds or even thousands of instances, but something about crossing into tens of thousands of concurrent instances caused cascading failures.
After two weeks of debugging, we discovered the issue was in a dependency we hadn't considered at scale. At cloud scale, even seemingly unrelated components become bottlenecks.
The key insight: Problems that are invisible at small scale become catastrophic at cloud scale. Performance issues that don't matter for 100 users become deal-breakers for enterprise customers running 10,000 instances.
What this means practically:
- Test at realistic scale from day one, even if it's expensive
- Build circuit breakers and graceful degradation into everything
- Assume every system component will eventually become a bottleneck
Lesson 3: Developer experience trumps feature richness every time
Three years ago, we launched a machine learning service with dozens of configuration parameters and support for multiple ML frameworks. Our engineering team was proud of the flexibility and power we'd built. Customers hated it.
Meanwhile, a competitor launched with just a few configuration options and support for one framework. Their adoption rate was significantly higher than ours.
The lesson: Cloud customers—especially developers—value simplicity and reliability over feature richness. They want to solve business problems, not become experts in your service configuration.
We redesigned our ML service around a few simple use cases: image recognition, text analysis, and predictive analytics. Each had smart defaults and one-click deployment. Adoption increased dramatically within months.
What this means practically:
- Design for the 80% use case first. Advanced configuration can come later
- Make the first five minutes magical. If users can't get value quickly, they'll never see advanced features
- Default configurations should work for most customers without modification
Lesson 4: Pricing is your most powerful product feature
I used to think pricing was a business decision that happened after product decisions. I was completely wrong. In cloud services, pricing model IS product strategy.
I've seen how different pricing approaches can completely change customer behavior patterns. A service priced one way encouraged customers to consolidate usage into fewer, larger deployments. When the pricing model changed to align better with cloud-native practices, customers naturally adopted more distributed architectures that made better use of the platform's capabilities.
What this means practically:
- Your pricing model shapes customer behavior more than your documentation
- Align pricing incentives with the behaviors you want to encourage
- Simple pricing beats optimal pricing every time
Lesson 5: Enterprise sales cycles will derail your roadmap (if you let them)
"A major enterprise customer is evaluating our platform for a seven-figure deal, but they need custom VPC peering by Q4." Sound familiar? Large enterprise deals create gravitational pull that can distort your entire product strategy.
I've seen cloud products become Frankenstein monsters because PMs tried to satisfy every enterprise requirement. The result: products that serve 10 large customers well but provide poor experiences for 10,000 smaller ones.
The framework that saved me: For every enterprise-driven feature request, ask three questions:
- Can we solve this with configuration instead of code?
- Will this benefit our broader customer base within the next year?
- Is this customer willing to pay enough to justify the true cost of building and maintaining this feature?
If the answer to any question is no, find an alternative solution or walk away from the deal.
What this means practically: Enterprise customers are important, but don't let their specific needs hijack your product vision. Build a platform that scales to thousands of customers, not a consulting service for a select few.
Lesson 6: Regional expansion is harder than it looks
"We'll just deploy our service to three new regions next quarter." This sentence has haunted more cloud product roadmaps than any technical debt or competitor pressure.
Regional expansion sounds straightforward—copy your infrastructure to new data centers, update your routing, and you're done. In reality, every new region introduces complexities you didn't anticipate:
- Data residency and compliance requirements vary dramatically
- Network latency between regions affects service dependencies
- Local infrastructure providers have different capabilities and limitations
- Support and operations coverage becomes exponentially more complex
We spent many months getting our storage service stable in international regions because we hadn't considered how network partitions between regions would affect our consistency guarantees.
What this means practically:
- Plan for regional expansion from day one, even if you're starting with one region
- Build services that can operate independently when inter-region connectivity fails
- Factor compliance and data residency requirements into your core architecture decisions
Lesson 7: Your monitoring strategy is your product strategy
At cloud scale, you can't rely on customer reports to understand product health. By the time users complain, thousands of workloads are already affected. This makes monitoring and observability critical product capabilities, not operational afterthoughts.
But here's what took me years to understand: the metrics you choose to monitor determine which problems you'll solve and which you'll ignore.
When we focused primarily on availability metrics (uptime, error rates), we built a reliable but slow service. When we added performance metrics (latency, throughput), we discovered that a significant portion of our "successful" API calls were taking far too long to complete. Customers weren't reporting this as downtime, but they weren't happy either.
The breakthrough insight: Your monitoring dashboard should reflect customer outcomes, not just system health.
What this means practically:
- Monitor business metrics alongside technical metrics
- Track user workflow completion rates, not just API success rates
- Build alerting around customer impact
Lesson 8: Platform thinking beats product thinking at cloud scale
The biggest mindset shift in cloud product management is moving from "product thinking" to "platform thinking." Traditional products solve specific problems for specific users. Cloud platforms enable other people to solve problems you haven't even imagined yet.
This shift changes everything about how you evaluate features, prioritize development, and measure success.
Product thinking: "How can we build the best machine learning inference service?" Platform thinking: "How can we enable developers to build any machine learning application they can imagine?"
The difference shows up in dozens of daily decisions:
- API design: Platform APIs need to be composable and extensible, not just functional
- Feature prioritization: Platforms prioritize building blocks over complete solutions
- Success metrics: Platform success is measured by what others build on top of you, not just direct usage
When we redesigned our compute service with platform thinking, adoption by ISVs and solution builders increased substantially because they could build products we never would have created ourselves.
What this means practically:
- Design APIs that can be combined in unexpected ways
- Build primitives that enable solutions rather than complete solutions
- Measure ecosystem health alongside direct product metrics
The meta-lesson: embrace complexity, but hide it from users.
All eight lessons point to a fundamental truth about cloud product management: you're managing complexity that users never want to think about. Regional failover, auto-scaling, security patching, compliance, data replication—these are the problems cloud services solve so developers don't have to.
The art of cloud PM is building sophisticated systems that feel simple. This requires a different set of skills than traditional product management: you need to understand distributed systems, operational complexity, and infrastructure economics while still focusing relentlessly on user experience.
But when you get it right, you're not just building products—you're building the foundation that enables thousands of other people to build products. That's what makes cloud product management uniquely rewarding and uniquely challenging.
After eight years, I'm still learning. Cloud computing is evolving so rapidly that strategies that worked two years ago are obsolete today. But these eight lessons have remained constant, forming the foundation for every successful cloud product decision I've made.
The cloud industry needs more product managers who understand these realities. Because ultimately, the quality of cloud platforms determines the pace of innovation for entire industries.
About the author
Rishab Jolly
With a deep background in cloud computing, observability, and product management, Rishab Jolly drives innovation as a Senior Product Manager at Microsoft. He leads strategy and execution for Azure Application Insights, helping businesses around the world monitor and optimize their digital experiences. A product thinker at heart, Rishab is passionate about building solutions that balance customer needs with business growth. Beyond the world of tech, he’s a podcaster, dog dad, and travel enthusiast. Whether he’s designing better monitoring tools or sharing leadership insights with his 20K+ LinkedIn community, Rishab blends curiosity, creativity, and customer obsession into everything he does.