Learn how reframing modernization as a product strategy, instead of a code exercise, helps teams accelerate value delivery, lower costs, and unlock scale through clear goals, strong leadership, and true product-engineering partnership.
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Jason McFadden is Principal Strategist, ISV & SaaS at Caylent. He helps SaaS leaders scale with clarity, speed, and confidence, bridging the strategist’s view with the operator’s urgency to turn AI, cloud, and product strategy into shipped work and measurable results. He scaled Book4Time to $2.5B in annual transactions, co-founded Avail, served as Entrepreneur in Residence at Platform Calgary, and holds the AWS Certified AI Practitioner credential. A 15-time keynote speaker, he has delivered talks at SaaS North, Collision, Elevate, Mesh, and other major stages. His talks show how AI and cloud are reshaping the way companies build, compete, and scale and how leaders can turn that shift into value that lasts.
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Anjanette Houser is Director of Product Management at Caylent, where she partners with clients to design AI-powered solutions and scale product practices. With deep expertise in HealthTech, SaaS, and digital consulting, she has a proven track record of turning complex technical challenges into user-focused outcomes. Anjanette thrives on building strategies that balance innovation with clarity while empowering teams through mentorship and collaboration. Outside of work, she enjoys gardening, cooking for her family, and following her favorite band, Ween.
View Anjanette's articlesMost modernization efforts fail because they focus on code instead of outcomes. This article reframes modernization as a product strategy — one that unlocks velocity, experimentation, and scale when it’s tied to clear goals and strong product leadership.
In this blog, you’ll learn:
If your roadmap is stuck or your platform can’t keep pace with ambitions, modernization may be the key. Modernization can’t be treated as an engineering initiative, but embraced as a product strategy.
Modernization is everywhere. It’s driving boardroom conversations, reshaping roadmaps, and creating pressure to move faster. Customers expect it, and teams feel the urgency. The challenge is that many organizations respond by rushing straight into delivery. They refactor stacks, rebuild services, or swap out tools without pausing to ask what the effort is truly meant to achieve.
Modernization delivers the how, but without a clearly defined why, the effort becomes spend without payoff.
Legacy systems don’t just slow down engineers. They slow down the entire business. Decisions get delayed, experiments stall, and launches lose momentum. A new pricing model might never advance because usage data is fragmented. Onboarding experiments collapse under hard-coded flows. Even major product releases struggle to escape a web of brittle integrations. What looks like an engineering bottleneck is actually a systems bottleneck.
This is where product leadership becomes critical. At Caylent, we’re known for moving fast and delivering technically sophisticated solutions. But speed without direction is a gamble. You might ship quickly, but will it create real value, be usable, or scale effectively? Product leadership provides that clarity by defining and driving outcomes, ensuring we focus on the right things at the right time for the right reasons. That alignment is what prevents waste, keeps teams focused, and creates lasting value.
When Product brings clarity, modernization delivers speed. Together, they unlock long-term success.
Most modernization efforts fail because they start with technology. Teams chase architectural purity, rebuild services, or plan massive rewrites without tying them to business outcomes.
The solution is to focus modernization on the parts of the application that are slowing you down. Target the constraints that block key product initiatives, delay launches, or add risk every time you ship.
Modernization only works when it’s tied to velocity. By velocity, we don’t just mean speed. We mean the ability to ship reliable code frequently, reduce lead time from idea to release, onboard new users and teams without friction, and respond to market shifts without re-architecting your platform. True velocity is the combination of technical flexibility, operational readiness, and product confidence, and modernization should accelerate all three.
This requires product and engineering working together, not just to reduce tech debt but to unlock speed where it matters most.
When Product is part of an engagement from the beginning, teams gain the structure and alignment they need to succeed. Product ensures that:
The impact of strong product leadership isn’t always visible in a Git repo, but it shows up in every decision downstream. Engineers thrive when the “why” is clear. With a clearly articulated “why,” developers can build with confidence, challenge assumptions with purpose, and make technical decisions that directly support meaningful outcomes.
The most successful modernization projects don’t start with technology. They start with curiosity. What are we solving? Why now? For whom? And how will we know when we’ve succeeded?
Product, at its core, produces clarity. And clarity multiplies the value of every other investment.
When done through a product lens, modernization reshapes a company’s ability to execute across five dimensions:
Legacy systems don’t just slow engineers down. They slow down decision-making, product iteration, and cross-team alignment.
Why? Because they embed tribal knowledge, brittle processes, and invisible dependencies that make even small changes risky. What seems like a small change can quickly spiral into risk: one deployment threatens to break several others, and suddenly every release needs another meeting, a workaround, or an all-hands fire drill. In that sense, technical debt isn’t just technical, it’s organizational.
Modern platforms shift the equation. By decoupling services, improving observability, and embedding automation in testing and deployment, they allow teams to move in smaller, safer steps. Infrastructure as code, feature flags, and preview environments make it possible to experiment without compromising stability. Instead of waiting weeks for a release window, product teams can validate hypotheses in real time.
This shift changes the rhythm of delivery. When teams can deliver value quickly, they build confidence. That confidence unlocks more collaboration, more experimentation, and more willingness to invest in platform improvements.
Modernization acts less like a milestone project and more like a flywheel, constantly reinforcing itself.
The impact extends across the organization. Faster delivery tightens feedback loops, streamlines onboarding, strengthens product–platform alignment, and enables iterative integration of user and business feedback, which is often overlooked in traditional mindsets.
Over time, modernization stops being a singular initiative and instead becomes the way the business naturally operates.
When change is expensive, every decision becomes high stakes. Teams often delay improvements, hesitate to experiment, and stick to ideas that feel “safe.” By contrast, lowering the cost of change opens the door to more experimentation. Teams can test, learn, and adapt without needing perfect foresight. That kind of agility creates a competitive advantage, because innovation isn’t about big bets; it’s about learning faster than the market.
Decoupled services help by reducing the blast radius of change. A single component can evolve without risking the whole system. CI/CD practices add another layer of reassurance: automated tests, consistent deploys, and quick rollbacks that make change more predictable. Instead of hoping things work, teams gain the confidence of knowing they can, and that if something doesn’t, it can quickly be undone. That confidence slashes risk, cost, and anxiety.
Strategy isn’t just choosing a direction. It’s knowing when to change course, and why that decision matters. Lowering the cost of change gives leaders more opportunities to adjust, whether in response to competitors, customers, or market shifts, without needing to rebuild everything from scratch. It makes adaptability part of the system. And in fast-moving markets, adaptability is often what separates those who keep pace from those who fall behind.
Autonomy helps remove common bottlenecks. Instead of waiting on centralized approvals, platform teams, or cross-functional handoffs, teams can move at their own pace. When they own their domain end-to-end, they tend to move faster and take greater care. Speed improves, but so does quality, because accountability sits closer to where the work happens.
Autonomous teams also tend to invest in their own velocity. They build internal tooling, improve test coverage, and streamline deploys in ways that are tuned to their needs. These may seem like small investments, but over time they compound. The result is less wasted effort, faster delivery, and more capacity for product work.
Ownership changes the conversation. Questions shift from “who’s going to fix this?” to “how do we prevent it next time?” With true ownership, teams stop throwing work over the wall. They make better tradeoffs, design with maintainability in mind, and take pride in outcomes rather than just outputs. Decision-making moves closer to the problem, and accountability moves closer to the user.
Legacy environments often slow progress in ways that go beyond outdated code. Hidden dependencies, fragile integrations, and layers of approvals make even small changes feel risky, which can create hesitation and reinforce a culture of caution over experimentation.
In contrast, modern platforms are designed with experimentation in mind. They provide reusable infrastructure like feature flagging, A/B testing frameworks, observability, and deployment automation, making it easier for teams to focus on ideas rather than reinventing the wheel. This creates an environment where cycles move faster, bets feel smaller, and the risks of trying something new are easier to manage.
Organizations that are able to test ideas frequently tend to gain an edge. They learn faster, adapt quicker, and uncover value others might miss. They develop the ability to learn faster, adapt quicker, and uncover value others might miss. Over time, this creates a flywheel where experimentation drives better decisions, stronger outcomes, and ongoing innovation.
Importantly, this approach enables teams to fail quickly, which is a key part of experimentation. Those who embrace this mindset see its benefits and make it a natural part of their culture. In this way, testing isn’t just a tactical advantage. The best outcomes are often rooted in fast failures, embedding learning into the very fabric of the company.
Rigid systems often hardcode assumptions about how your business works, such as pricing models, customer types, or data flows. When opportunities for growth appear, whether that’s entering new regions, introducing bundles, or opening new channels, those systems become the bottleneck.
Modern architectures are designed to avoid that trap. By relying on decoupled services, APIs, and cloud-native infrastructure, organizations can more easily tap into new markets, adapt offerings, or test entirely new products without overhauling their core systems. This kind of flexibility allows teams to respond more quickly when opportunities arise, without derailing the entire roadmap.
Disruption is less about competition alone and more about timing. Market shifts don’t necessarily reward the company with the best long-term strategy, but rather the one that can act on it in the moment. Modern platforms create space for that agility, turning disruption from a threat into an opening to seize.
The stack can be modernized by cleaning up the architecture, moving to containers, adopting event-driven patterns, and automating deployments.
But none of it matters if your teams can’t move faster.
That’s the test. Does modernization actually increase velocity? If every team is still guessing at how to build, wire things up, or push to production, then you’ve just made the platform more complicated instead of more powerful.
Enablement is what turns modernization into momentum.
It’s how you make good decisions repeatable, best practices discoverable, and infrastructure usable by the people who need it most, the builders.
What that looks like in practice:
If modernization is the engine, enablement is the accelerator.
Modernization isn’t just a technical upgrade. It’s a product enabler. Product leaders need a framework to connect modernization to faster delivery, better customer experiences, and business growth.
A simple set of questions helps connect modernization work to product impact:
As a product leader, facing a slow roadmap can feel frustrating. The good news is you don’t need to become a systems architect to fix it, but you do need a framework for prioritizing modernization so it directly supports your goals.
1. Find your friction
Start by reviewing the initiatives that should have already been shipped by now. What’s holding it back? Maybe it’s slow environment provisioning, tangled entitlements, missing usage data, or brittle billing logic. When you hear “that’s hard to change,” you’ve uncovered a constraint worth addressing.
2. Define the unlock
Every constraint, once removed, unlocks new possibilities. Could you ship faster? Run more experiments? Open a new customer segment? This is where you tie modernization back to business impact. It’s not about refactoring for its own sake, but about making progress visible and valuable.
3. Partner on the path
You don’t have to own the architecture, but you do share responsibility for the outcomes. Work closely with engineering to define success together. Keep the scope focused, iterate quickly, and demonstrate value early.
Modernization isn’t a single project you check off a list. It’s a series of strategic unlocks, and it’s too important to leave to engineering alone. How fast you learn, how often you ship, and how flexibly you grow are all shaped by these choices. That makes modernization core product territory.
We partner with SaaS companies to turn modernization into momentum. That means identifying the constraints that slow you down and building the systems that speed you up without requiring a full rewrite.
Our approach helps you:
We support you with:
Contact us today to see how we can help your organization.
Jason McFadden
Anjanette Houser
