Leadership lessons from sunsetting a product

Why sunsetting is a strategic necessity

In product development, we’re trained to chase growth - launching new features, scaling adoption, and expanding markets. But what happens when a product reaches the end of its lifecycle? Whether driven by poor financial performance, low demand, technological obsolescence, or portfolio optimization, the decision to sunset a product is often seen as a retreat, when in reality, it’s a strategic pivot.

I’ve led multiple product transitions, and one of the most transformative experiences came when I sunset a legacy platform that had served our clients for nearly a decade. It wasn’t easy. There were emotional ties, technical dependencies, and customer contracts to navigate. But it was necessary and it taught me that endings, when done right, can be just as powerful as beginnings.

The sunsetting framework

The framework offers a structured approach to decommissioning a product. Here’s how it unfolds:

Strategic planning

Every sunset begins with a question: Why now?

In my case, the platform was showing signs of fatigue, rising maintenance costs, declining usage, and a newer solution waiting in the wings. This platform, which was a decade old, was built on legacy and costly technology. I documented the rationale, aligned it with our business strategy, and presented a clear case to leadership. I received support from the entire C-suite, including the Chief Product Officer, who made the sunset a top priority for our team.

Cross-functional team formation

Sunsetting is a team sport. I assembled a cross-functional task force of approximately 20 core individuals to tackle this project, which spanned roughly nine months from initial planning to full decommissioning. The team was structured as follows:

· Product managers to lead strategy (2 people)

· Engineering to manage decommissioning (12 engineers)

· Legal and privacy to handle compliance (2 people)

· Finance to assess impact (1 person)

· Marketing and comms to shape messaging (2 people)

· Client success to guide transitions (1 person)

One lesson I learned early: don’t underestimate the emotional impact on internal teams. While the broader organization was relieved about the change due to the platform's known issues, the core team felt a deep sense of loss. Engineers who built the product felt a sense of loss. I held retrospectives not just to plan, but to honor the work.

Execution plan and timeline

I created a phased execution plan and roadmap:

· Internal announcement and alignment

· External communication with 12-month notice

· Migration support and training

· Final shutdown and post-sunset cleanup

I used tools like Aha! Roadmap and Confluence to track progress. Weekly standups kept everyone aligned. One unexpected challenge? A third-party integration with a vendor we’d forgotten about. It delayed our timeline by a month but reinforced the need for thorough dependency mapping.

Customer-centric transition

Our clients, a mix of small and large financial institutions, were understandably concerned about the shutdown. Many of them had built critical daily workflows around our platform, using it for tasks like managing customer data and processing financial transactions.

To ease their concerns and make the transition as seamless as possible, I offered a robust support package:

· Migration guides with step-by-step instructions to move their data.

· Webinars and Q&A sessions to walk them through the new solution's features.

· Dedicated support channels with transition specialists available to answer specific questions.

· A sandbox environment to allow them to test and get comfortable with the new solution before the final switch.

The goal was to make this feel like an upgrade, not a shutdown. As one client told us, "You made this feel like an upgrade, not a shutdown." That feedback was a powerful validation of my approach.

Legal, Financial, and Privacy Readiness

I meticulously prepared for the sunset by engaging three key teams: Legal, Finance, and Privacy. This process took approximately three months to complete.

• The Legal team reviewed all client contracts for exit clauses and drafted the official notification letters.
• The Finance team modeled the revenue impact and assessed the financial exposure of the shutdown.
• The Privacy team ensured we were compliant with all regulations, including GDPR, and confirmed our data retention policies were correctly followed.

A key takeaway: Start these conversations early. Legal and finance timelines often run longer than expected. I recommend dedicating a minimum of 4 to 6 months for these preparations to account for potential delays and ensure all compliance and financial matters are thoroughly handled.

Technical decommissioning

Engineering led the charge on the technical decommissioning, a process that took over six months from initial planning to final server shutdown.

The team followed a precise playbook to ensure a smooth "launch in reverse," which included:

· Identifying all middleware and API dependencies to prevent service disruptions.

· Scheduling data cleanups and server shutdowns in a phased approach.

· Reviewing vendor agreements for any final clauses or obligations.

· Deciding on code archiving vs. deletion to preserve institutional knowledge.

This process was not without its roadblocks. I faced a significant challenge in the early stages when Engineering discovered several undocumented dependencies on a different team's product, which required an unexpected two-week delay to resolve. Additionally, managing the phased data cleanup was complex due to the interconnected nature of the system, but the team's meticulous planning prevented any data loss. 

Despite these challenges, the team's precision and care ensured a successful final shutdown. One engineer described it as “launching in reverse” and they were right. It required the same precision and care.

Communication strategy

I built a layered communication plan tailored to our internal teams and the clients who relied on the platform for their operations. 

·  Internal updates via newsletters and town halls kept teams informed and aligned on the transition.

· External messaging through FAQs, webinars, and bulletins addressed client questions and guided them to the new solution.

· Sales enablement tools were provided to equip our client-facing teams with consistent messaging.

To humanize the shift from a decades-old system, I created a “sunset story” video. It helped build empathy and ensure a clear, unified message.

Documentation and evidence locker

I maintained a centralized repository:

· Project plans and issue logs

· Meeting notes and status updates

· Risk assessments and mitigation plans

This became our single source of truth and a valuable archive for future sunset projects.

Journey mapping and experience design

I mapped the customer journey:

· Before, during, and after sunset

· Pain points and unmet needs

· Opportunities to improve experience

This helped us anticipate friction and design smoother transitions. It also gave us insights into how customers perceived value and how to preserve it.

Measuring success and mitigating risks

I defined success by a set of clear metrics, and ultimately, achieved them.We defined success as:

· Executing the sunset within timeline: The project was completed within the planned nine-month timeframe.

· Maintaining customer satisfaction: Proactive communication and dedicated support helped us keep customer satisfaction high.

· Avoiding SLA breaches: I avoided any major SLA breaches throughout the transition

· Optimizing post-sunset performance: I successfully optimized the performance of the new solution.

I tracked risks weekly and had contingency plans for each. A key example was when a major client delayed their migration; our flexibility was key, and the company extended their support by 30 days to ensure a smooth and successful transition for their team.

Personal reflections

Sunsetting a product is emotional. It challenges your leadership, tests your empathy, and forces you to make tough calls. But it also brings clarity.

I’ve learned to:

· Communicate early and often to manage expectations and minimize surprises.

· Honor the work that came before to respect the team's contributions and mitigate a sense of loss.

· Focus on the future, not just the exit, by highlighting the new opportunities.

One of my proudest moments? Seeing the team that sunset the old platform become the architects of the new one. They didn’t just close a chapter, they wrote the next one.

Turning endings into strategic wins

The post-mortem for this project was overwhelmingly positive. Internally, it was seen as a major strategic success, as it freed up significant resources that had been tied to the legacy system. Our users' initial concerns quickly turned into appreciation, with many expressing how the new platform felt like a major upgrade to their daily workflows.

In the long run, this has profoundly benefited the company. We've not only cleaned up years of technical debt but also created a stronger, more efficient product portfolio. The successful sunset of the old platform laid the groundwork for future innovation and has become a case study for how to transform a challenge into a strategic advantage.