Rebooting a Stalled Modernization: From Legacy Monolith to Scalable, Product-Led Micro-services Platform

A market-leading digital music product company operating a 25+ year-old core platform, supporting both B2C and B2B users. The business had grown through years of incremental change and custom development, resulting in significant technical debt and organizational strain.

The client brought Connective in after a previous modernization effort stalled. Despite significant investment, the organization was left with:

• A deeply coupled monolithic architecture built on aging technology. Slow, high-risk release cycles where even minor changes required full redeployments. Limited ability to experiment, A/B test, or validate new ideas A growing skills gap between the platform’s complexity and the in-house team’s readiness

• Lack of a clear product strategy and prioritization framework leading to gut-driven decisions and long-cycle bets with uncertain ROI

• Low confidence across engineering and product teams that forward progress was achievable

Momentum had stalled, teams felt stuck, and leadership needed a partner who could reset the trajectory without overwhelming the organization.

The client needed more than a technical vendor. They needed a partner who could:

• Work with their teams, not around them

• Reboot a failed modernization effort

• Balance best practices with organizational reality

• Modernize not just the technology, but also how decisions were made

• Reduce risk while restoring confidence and forward motion

• Work with their teams, not around them

Connective was engaged to help the organization move again—technically, operationally, and strategically.

1. Pragmatic Modernization (Not Dogma). Rather than forcing the “perfect” architecture, Connective met the client where they were.

2. Designed a modern target architecture while sequencing adoption realistically.

3. Avoided premature complexity (e.g., Kubernetes) until the organization was ready

4. Focused on high-value, high-leverage areas first, rather than a full rewrite

5. Treated modernization as journey not a big-bang event

Player-Coach Partnership Model

1. Connective operated as an extension of the client’s team.

2. Made decisions with the client, not behind closed doors

3. Paired delivery with hands-on enablement and knowledge transfer

4. Introduced new tools and patterns incrementally, tied to real problems

5. Ensured the client could own and evolve the platform long after engagement

Product Strategy & Decision Discipline Modernization wasn’t only technical. Connective helped introduce:

• Structured backlog refinement and prioritization

• Value-based tradeoff discussions (who benefits, why now, at what cost)

• Early thinking around portfolio management and outcome-driven metrics

• A shift from intuition-only decisions to data-informed product strategy

This gave leadership language, structure, and confidence to make better bets.

• Technical Foundation Introduced a modular, decoupled architecture alongside the existing system

• Built a modern Next.js front end and new .NET-based APIs

• Containerized services using Docker and deployed via Azure App Services

• Positioned the platform for future Kubernetes adoption—without forcing it early

DevOps & Delivery Enablement

• Rebuilt inherited pipelines into standardized CI/CD templates

• Enabled consistent deployment patterns across teams

• Reduced risk through shared conventions and tooling

• Created reusable foundations the client can leverage independently

Operational Flexibility

• Enabled feature-level deployments instead of full-platform releases

• Introduced real feature flagging and “stealth” production releases

• Allowed teams to experiment, test, and iterate without destabilizing the platform

Collaboration Model What made this engagement successful was how the work was done:

• Daily collaboration between Connective and client engineer

• Transparent tradeoff discussions with leadership

• Continuous alignment across product, engineering, and operations

• A shared goal: build capability, not dependency

This partnership model directly addressed the shortcomings of the previous vendor relationship and rebuilt trust.

Immediate Outcomes

• Restored momentum after a stalled initiative

• Increased confidence across engineering and product teams

• Safer, faster releases with dramatically reduced blast radius

• A scalable foundation aligned to future growth

Predictable, Long-Term ROI

• Faster time-to-market for new features and experiments

• Reduced cost and risk of ongoing platform changes

• Improved ability to test ideas before making large investments

• A platform that can evolve with the business—rather than constrain it

Most importantly, the client moved from feeling stuck to feeling capable. The Takeaway Modernizing a legacy platform isn’t just about new technology—it’s about bringing the future into the present in a way teams can actually absorb. By combining pragmatic architecture, strong product thinking, and a true player-coach partnership, Connective helped this client reboot a failed effort and lay the groundwork for sustainable growth.