Imagine you’re the CTO of a digital bank. Your customers expect to open an account in minutes, transfer money instantly, access real-time spending insights, and get fraud alerts—all from their mobile devices. Behind the scenes, dozens of systems keep the experience flowing smoothly: core banking infrastructure, identity verification tools, AI-driven analytics, fraud detection engines, and customer service platforms—all owned by different teams, using different tools, across different geographies and time zones.
This is what digital product development looks like today. Gone are the days of predictable, linear release schedules. Modern digital product organizations operate in a fast-moving, interconnected environment where cross-functional teams build, release, and iterate in parallel. This enables rapid innovation, but it also brings tremendous complexity.
The Modern CTO’s Role
Today’s CTOs sit at the intersection of business strategy and product delivery. They’re accountable not simply for shipping code, but for shipping outcomes. That means navigating a complex web of priorities, platforms, and people to deliver innovations that move the business forward.
More and more organizations are embracing a “two-in-the-box” model, where Product Management and Engineering co-own outcomes. This model promises greater innovation and responsiveness—but only if both sides are tightly aligned.
That alignment is built on three things:
- Visibility across teams, tools, and workflows
- Shared accountability for business outcomes
- The ability to course-correct quickly as market conditions or customer needs evolve
Unfortunately, most organizations fall short in these areas.
According to Planview research, 45% of executives say they struggle to quantify ROI from digital transformation efforts. Many report months—even years—of delay in bringing new products or features to market.
But these challenges aren’t insurmountable. With the right solutions and approach, CTOs can streamline development, prioritize the most important work, and deliver faster—without sacrificing quality.
In this blog series, we’ll explore the most critical challenges facing today’s digital product organizations—from aligning strategy and execution to balancing innovation work with the effort required to keep platforms modern. Each post will explore a specific obstacle, unpack its real-world impact, and offer practical solutions that forward-thinking CTOs and product leaders are using to accelerate delivery, increase ROI, and build products that truly move the business forward.
Challenge 1: Driving Visibility and Strategic Alignment
Let’s start with one of the most fundamental obstacles to digital product success: lack of visibility and strategic alignment.
Understanding the Problem
Most digital product organizations suffer from a persistent disconnect: delivery teams execute work, but they have no idea how that work relates to business goals. Engineering teams may be hitting their sprint goals by completing story points and shipping small incremental features, but the larger initiatives that drive real business value may be delayed, deprioritized, or derailed.
Here’s what typical misalignment looks like on the ground:
- Development teams are measured on story points and sprint velocity, but these KPIs don’t relate to executives’ goals for customer acquisition, revenue, and retention.
- Product and engineering data lives in silos—spread across Jira, ServiceNow, Aha!, Excel sheets, PowerPoints, emails, and out-of-date dashboards.
- Product priorities regularly shift without notice and without consideration for impact to teams or strategy, making roadmaps obsolete within weeks, or even days, of their publication.
- Leaders use outdated, conflicting, or incomplete data to make critical decisions.
- No one has a clear line of sight into whether current work is advancing the company’s most important goals.
This disconnect creates a “black box” effect: lots of motion, but uncertain progress.
The Impact of Poor Visibility and Misalignment
When CTOs and product leaders lack a clear line of sight into what teams are working on and how that work relates to strategic goals, the consequences are far-reaching and deeply felt across the organization. What might start as small inefficiencies can compound into critical business failures.
Let’s break down the real-world impact in more detail:
1. Wasted Effort on Low-Impact Initiatives
Without a unified system to track work against strategic priorities, teams often default to completing the next item in their backlog—whether or not it’s the most valuable or urgent thing to do. They may deliver on time, but they deliver the wrong thing.
Real-world example: A development team might spend weeks perfecting a new UX enhancement for a mobile app while a high-impact compliance update sits on the back burner, potentially putting the business at regulatory risk.
The result: Engineering resources are consumed by features that don’t contribute to business goals. Morale takes a hit when teams face harsh criticism for failing to meet critical regulatory requirements.
2. Delays in Product Launches
Strategic product launches often involve complex dependencies that span multiple teams and tools. Without clear visibility into how those pieces fit together—or where things are slipping—delivery timelines become unreliable.
Real-world example: A critical integration point with a third-party vendor gets delayed by two weeks, but no one on the primary team notices until the end of the sprint. Now, the entire launch is pushed back a month.
The result: Deadlines are missed, customer commitments slip, leadership loses confidence, and downstream plans for go-to-market campaigns must be rescheduled and prioritized.
3. Missed Market Opportunities
In today’s competitive landscape, timing is critical. Delays in feature releases, market expansion, or regulatory response can mean missed opportunities and lost revenue.
Real-world example: Your competitors roll out real-time account insights before your product is ready. Customers churn, new opportunities stall, and your value proposition becomes harder to defend.
The result: Instead of leading the market, you’re stuck playing catch-up with a product roadmap that reacts to change rather than driving it.
4. Lost Revenue and Reduced ROI
When product development isn’t clearly tied to business objectives, it’s difficult to forecast ROI—and even harder to capture it. Misaligned initiatives consume time, money, and precious team capacity without delivering measurable value.
Real-world example: A product leader greenlights a passion project based on personal interest rather than market demand. Despite months of development, the feature sees little adoption, as it doesn’t solve a known customer problem or align with strategic goals.
The result: Resources are spent with minimal return. Finance teams grow wary of funding new initiatives, and future innovation efforts face increased scrutiny.
5. Falling Behind the Competition
Perhaps the most dangerous consequence of poor visibility is inertia. When organizations can’t see what’s happening, they can’t course-correct quickly and end up moving slower. In a market driven by speed, that’s a killer.
Real-world example: A competitor with streamlined delivery capabilities can test, launch, and iterate on a new product in six weeks. Your teams are spending half their time in meetings just to keep each other up to date, so it takes them six months to reach the same milestone.
The result: When you’re slow to respond, people notice. You risk becoming irrelevant as analysts critique your ability to deliver and customers choose faster, more responsive alternatives.
6. Erosion of Team Collaboration
Misalignment impacts outcomes and weakens the collaboration that drives innovation. When Product, Engineering, and executive stakeholders have conflicting views on progress or priorities, teamwork breaks down.
Real-world example: Product managers think work is progressing because story points are being burned down. Engineering teams are frustrated because shifting priorities are constantly derailing their work. Business leaders are in the dark about delays.
The result: Finger-pointing replaces partnership. Silos deepen. And it becomes harder to align on future goals because the present feels so disjointed.
How Planview Helps: A Unified View of Initiatives, Work, and Outcomes
Planview addresses this challenge head-on by giving CTOs and product leaders a single, connected view of how work is progressing across the organization, where it is at risk, and how it aligns with strategic priorities.
Here’s how it works across three critical dimensions:
1. Alignment to Strategic Priorities
Planview connects the dots between high-level business strategy and day-to-day execution. It enables real-time tracking of how work aligns to your priorities and highlights potential risks to the plan, so you can spot disconnects early and adjust course before it’s too late.
Key capabilities include:
- Real-time tracking of development activities against strategic objectives
- AI-powered insights to flag misaligned work before it becomes a sunk cost
- Portfolio-level visibility that uncovers dependencies across teams, tools, and time zones
With this level of transparency, you’re not relying on endless status meetings, outdated data, or gut checks. You have live insights into how every epic, feature, and story ladders up to your most important goals.
2. Outcome-Based Analytics
Traditional engineering metrics like velocity, burndown, and story points tell you what’s getting built, but they don’t tell you how (or whether!) it matters.
Planview elevates the conversation by integrating business value into your analytics. That means:
- Delivery data is tied to real business outcomes
- Performance is evaluated against company-wide goals, not team-level activity
- You can see the connected value being delivered as work progresses, not just after a single feature goes live.
This shift from focusing on output to driving outcomes enables CTOs to lead with value instead of execution. It also equips them to engage CFOs and board members in more strategic, ROI-driven conversations.
3. AI-Powered Decision Support
In fast-moving environments, reactive decision-making is too slow. Last quarter’s plans might not be relevant anymore. Planview’s AI capabilities help CTOs anticipate issues and flag risks before they derail progress.
Its AI-powered platform helps organizations:
- Forecast delivery timelines based on historical and real-time data
- Identify risks, blockers, and bottlenecks before they slow down delivery
- Recommend re-prioritizing work based on shifting goals or constraints
With AI working in the background to surface these insights proactively, CTOs can make faster, more informed decisions—and empower teams to do the same.
Real-World Example
Let’s go back to our digital banking scenario.
You’ve got an initiative to launch a new AI-driven savings feature by the end of Q3. It involves three teams working across five tools. Early dashboards show progress, but delays are creeping in. Without integrated visibility, you’d only find out once the deadline slips.
With Planview:
- You immediately see that one team is working on a feature that isn’t tied to the Q3 goal
- AI flags a dependency risk on an API integration that hasn’t started yet
- Outcome metrics show that another team’s velocity is high, but they’re building a backlog of non-priority features
Now you can intervene early, reassign work, align priorities, and keep your initiative on track—before it becomes a fire drill.
Turning Visibility into a Competitive Advantage
When you can’t see clearly, it’s hard to move fast, and even harder to move in alignment with strategic goals. That’s the challenge many modern CTOs face: trying to steer a high-speed product organization with foggy visibility and a disconnected sense of progress. But it doesn’t have to be that way.
With unified insights and outcome-based alignment, you’re not just tracking work—you’re building a clear path from idea to impact. That clarity turns hesitation into momentum so your delivery teams can keep you ahead of your competitors.
But clarity alone isn’t enough if your tools don’t talk to each other.
In our next blog, we’ll tackle the challenge of unifying fragmented toolchains. You’ll learn how disconnected systems create drag, why patchwork solutions fall short, and what it takes to build a cohesive toolchain that accelerates collaboration and delivery across teams.
If you’re ready to see this in practice, watch a demo of Planview’s digital product development solution and discover how top organizations are turning strategy into execution to deliver faster and drive greater impact.
