Internal Roadmap Transparency

Context

The symplr Workforce segment was in a communication bind. On paper, our core products looked fantastic. They were the prized cash cows of the symplr portfolio, generating the recurring revenue needed to fund ongoing acquisitions. But under the surface, these products had aging tech stacks. We needed to keep our installed customer base engaged, while also helping internal teams understand why we had to dedicate limited engineering capacity to behind-the-scenes improvements.

This wasn’t unique to our business unit. Many of symplr’s recent acquisitions faced the same challenge. The difference? Not all of them were profitable. Clear internal communication became essential to our success.

Problem: How do you create a communication model that:

  • Helps internal stakeholders understand engineering trade-offs?

  • Keep customers focused on value?

  • Preserves trust in the product during long-term transitions?

What I Did: created a visual and strategic framework I called The Iceberg Model, diving engineering capacity into two parts:

*Note: the picture below is an illustrative example only.


Top of the Iceberg: These are the enhancements we want customers focused on: UX improvements, automation, and better workflows. This part of the roadmap needs storytelling and customer-facing plans. For an example of how we improved our release management proves to embed value storytelling see Release Management: Reimagined.

Bottom of the Iceberg: This is where Product Managers get pulled under. It includes critical work that we don’t want taking up customer headspace but must be done to reduce risk and enable future scalability. Bottom of the iceberg work includes:

  • Security: Proactive and reactive work, from penetration tests to urgent patching. Always the #1 risk.

  • Tech Stack Upgrades: For example, upgrading a soon-to-be unsupported version of Python, SQL, or any other critical technology before it becomes a crisis.

  • Engineering Efficiency: Improving tooling, cleaning up legacy code, or running investigative spikes to prevent bugs and improve long-term velocity.

I worked with engineering, security, and architecture teams to map and communicate this work in ways leaders could understand, emphasizing risk if not done rather than technical jargon.

Results

The Iceberg Model became a go-to framework for internal roadmap planning. It helped:

  • Product leaders frame and justify capacity trade-offs

  • Sales and Customer Success understand why we couldn’t say “yes” to every ask

In short: it helped everyone keep the focus where we wanted it to be: the top of the iceberg.

You’ll Know You’re Successful When…

Your internal partners start defending your roadmap for you, because they understand and trust the strategic rationale behind your priorities.

Relevant Skills

  • Product Communication & Roadmap Framing

  • Cross-Functional Alignment (Sales, CS, Engineering, Security)

  • Capacity Planning & Trade-off Management

  • Technical Fluency in Security, Infrastructure, and Refactoring

  • Strategic Storytelling for Internal and External Stakeholders

Curious how to align internal interests for better products?  Let’s connect and chat about building scalable, customer-centered systems.