Aligning product and engineering around a cloud-first strategy

Context snapshot

Organisation: B2B Tech startup

Domain: Data discovery, governance, and compliance

Customers: Enterprise organisations

Technology shift: On-premise to Cloud-native

Leadership challenge: Product and engineering alignment under constraint

Executive tension

This Tech startup operated in a fast-moving and highly regulated market, serving enterprise clients under increasing compliance pressure. The business faced a critical strategic tension.

Its incumbent product was:

• Generating revenue

• Deployed on-premise

• Built on an architecture approaching obsolescence

At the same time, a new product had been developed:

• Designed around the needs of a single pilot client

• Architected for on-premise deployment

• Misaligned with the market’s accelerating shift to Cloud

Resources were limited.

Leadership attention was split.

The organisation could not afford to fully invest in both directions — yet delaying decisions increased technical debt, diluted focus, and slowed progress.

Reframing the problem

This was not a technical capability or roadmap problem.

It was a clarity, alignment, and decision-making problem at the intersection of strategy, product, and leadership.

The organisation was caught between:

• Protecting short-term revenue

• Building long-term relevance

The new product had been shaped too closely by a single client context, while architecture decisions defaulted to on-premise, locking in constraints the market was moving away from. Teams were busy, but unclear what “good” looked like over the next 12–24 months.

What the leadership team did not need was:

• More detailed plans

• More features in the backlog

• More pressure on delivery

What it needed was:

• A shared view of strategic intent

• Explicit trade-offs between short-term revenue and long-term viability

• Clear product pathways and investment choices

• Leadership alignment strong enough to hold difficult decisions

In short, the organisation needed to make deliberate choices — and organise around them.

How we worked

1. Create leadership alignment around the choices

Through facilitated workshops and team coaching with Product and Engineering leadership, we worked to:

• Surface underlying assumptions

• Make tensions explicit

• Separate customer-specific needs from product strategy

This shifted conversations from opinion-driven debate to shared understanding.

2. Use strategic mapping to frame trade-offs

Strategic maps were used to:

• Clarify the role of the incumbent product

• Define the ambition for the next-generation offering

• Make investment trade-offs visible and discussable

This enabled leadership to:

• Agree where to sustain, simplify, or sunset

• Identify what needed to change for the new product to scale

3. Redesign the product direction

With clarity established:

• The new product was redesigned as Cloud-native, not retrofitted

• Architecture decisions were revisited to support scalability and reuse

• Teams were reorganised around clearer product intent

The incumbent offering was stabilised, while selected components were:

• Extracted as standalone services

• Open-sourced where appropriate

• Used to support client transition rather than block progress

4. Strengthen leadership coherence

Individual coaching with the CTO focused on:

• Leading distributed teams across geographies

• Holding alignment under pressure

• Communicating strategic intent consistently

This strengthened execution without reverting to command-and-control.

Evidence of movement

The shift became visible over time.

Leadership alignment improved around a single, coherent product direction. Engineering focus increased as priorities stabilised, reducing fragmentation and rework. The new product successfully transitioned to a Cloud-native offering, improving market fit and traction.

Existing clients were progressively transitioned rather than stranded, protecting revenue while enabling evolution.

For the CTO, decision-making clarity improved, alignment across Product and Engineering strengthened, and leadership presence across distributed teams became more consistent. Leadership energy shifted away from arbitrating competing demands toward enabling focus and progress.

The organisation moved from tension-driven compromise to deliberate strategic execution, which allowed it to survive difficult conditions during COVID and grow steadily in the years that followed.

Inviting your reflection

If your organisation is trying to protect today’s revenue while building tomorrow’s product, struggling to prioritise under technical and resource constraints, or debating roadmaps without resolving trade-offs —

the issue may not be capability.

It may be clarity, alignment, and leadership coherence.