From ambiguity to action

Reframing a multi-million dollar last-mile problem into a scalable strategy

Organisation

Woolworths Group

Role

Lead Service Designer

Year

2025

read time

7 minutes

Summary

Woolworths Group’s last-mile delivery service, HomeRun, was incurring millions in annual overage fees due to delivery inefficiencies. These were driven by both controllable factors like poor driver behaviour and uncontrollable ones such as weather events.

I was engaged as Lead Service Designer on a six-month secondment to shape the strategic direction of the Control Tower initiative. The brief lacked clarity, as the problem was not yet well understood; surfacing and defining it became the focus of the engagement. With varied stakeholder expectations and ongoing organisational change, the landscape was complex but full of opportunity.

Over six months, I reframed the problem, led deep discovery, uncovered critical gaps, and helped secure funding for two delivery squads by defining a clear, prioritised and actionable roadmap.

Where the business thought the problem was

Early on, it was believed that the core issue was:

Each delivery route runs 14% over the planned time. If we can monitor performance in real time and intervene early, we can reduce costs and improve efficiency.

This performance gap was costing the business millions in overage payments to their delivery partner. A 'control tower' was proposed as a solution – envisioned as a physical command centre or digital platform. However, the concept was loosely defined and interpreted differently across stakeholder groups.

What discovery revealed about the real problem

The real issue wasn’t a lack of visibility. Rather, it was a lack of usable, real-time data and defined responsibility.

The delivery partner already had contractual obligations to monitor and manage most performance exceptions. Meanwhile, HomeRun's own teams were drowning in reactive work, unable to scale or respond proactively. Instead of investing in a new 'tower' to monitor everything, the real opportunity was to focus on:

Making operational data usable

Streamlining communication and response to events

Creating strategic alignment on what Control Tower actually meant

Leading strategy in a complex, ambiguous environment

This was an independent, discovery-led engagement – I led the work from scoping through to executive presentation.

I partnered closely with the Director of HomeRun and collaborated with senior stakeholders across Compliance, Customer Support, Enablement, Fleet Operations, Routing, and Safety. While I reported into the Group Product Manager, I had full ownership of the research approach, stakeholder engagement, and synthesis of insights.

I worked autonomously to navigate ambiguity and build alignment, and in partnership with the Group Product Manager, delivered a strategic roadmap that unlocked funding for future delivery.

How I uncovered the full picture

To reframe the problem, I designed and led a comprehensive 6-month discovery across the business:

17 x 1:1 stakeholder interviews (1 hour each) to understand workflows, pain points, expectations and Control Tower interpretations

6 x 1.5-hour cross-functional workshops to synthesise business unit needs

8-hour ride-along with a delivery driver to observe real-world operations

3 hours onsite at the Customer Support call centre to understand exception handling

3 product demos with external vendors to test solution feasibility

Co-led capability assessments and opportunity mapping with Product leadership

Redefining the problem and shaping the right investment

The central insight was:

Control Tower isn’t a place or a monolithic platform — it’s an ecosystem of data, capabilities and interventions designed to proactively manage events within a driver’s shift.

This insight was communicated through:

A shared vision statement everyone aligned to

Value proposition canvases for six stakeholder groups

A prioritised pain/gain/jobs framework

A 4-year Now / Next / Later roadmap

Clarity on what not to build

Additionally, a new contract signed during the project held the partner more accountable for performance – reinforcing the strategic pivot that had been recommended.

Reflections on impact, growth, and grit

This was a solo mission during a business-wide restructure that ultimately made both my secondment and substantive roles redundant. With limited guidance, few clear metrics, and a highly ambiguous problem space, I delivered clarity and secured buy-in for the next stage of delivery.

What I’d refine next time

Next time, I’d establish a small support group of key and secondary stakeholders early in the engagement. A defined circle of six cross-functional voices would have helped accelerate alignment, provide ongoing access to operational context, and reduce dependency on any single stakeholder.

© 2025 Jordan Skedgwell

© 2025 Jordan Skedgwell

© 2025 Jordan Skedgwell