Milo
Drake

Two luxury safari camps. Six months from opening. No CRM, no booking flow, no trade relationships, no reporting infrastructure. The founders knew exactly how to run extraordinary experiences in the bush. The commercial architecture behind it did not yet exist.

I was brought in as the pre-launch commercial strategist and designed the full operating blueprint from zero. That meant mapping the entire enquiry-to-deposit process: how a lead captured on the website should move through a structured pipeline, what follow-up cadence would work at each stage, and what needed to be in place before the first booking could be taken with confidence.

Alongside the booking flow, I built the trade distribution strategy. Luxury safari bookings do not come through Google; they come through a small network of specialist travel advisors and agencies in the UK, US, and Europe. I identified the priority advisors, designed the outreach approach, built the trade pack and quote-fast kit, and set the cadence for ongoing relationship management.

The systems layer underpinned everything. A Pipedrive CRM structure with custom pipeline stages and clear ownership logic. A six-pillar master tracker covering demand, trade, product, content, operations, and reputation. A weekly commercial operating pack designed so founders could review pipeline status and pending decisions in under ten minutes, wherever they were.

This is the kind of work that does not show up on a highlight reel. It is the difference between a beautiful product that struggles to fill beds and one that opens with the infrastructure to convert interest into deposits from day one.

Before "retail media" became a boardroom buzzword, Deliveroo was quietly building a version of it: Sponsored Positioning, a paid placement product that let restaurant partners buy visibility in specific zones and categories. The concept was straightforward. The commercial operation behind it needed building.

My job was to manage the partner selection and onboarding process across the entire UKI market, deciding which restaurants would go into the MVP, across which regions and which zones within cities. 2,000 placement slots. 200 zones across the UK and Ireland. 10 restaurants per zone maximum, with rules designed to protect both commercial integrity and the user experience.

I built the tracking infrastructure that made this manageable: a live tracker that captured partner status by zone, managed exclusivity decisions, and fed the commercial logic into the weekly tech deployment. Exclusive partners were a priority, and commercial incentives were used to get high-value restaurants onto Sponsored Positioning before the product went wide.

The broader lesson was one I have carried forward: new revenue products do not fail because the idea is wrong. They fail because the operational layer between concept and execution is not built properly. Build the tracker, own the data, manage the exceptions, feed the machine. That is how an MVP becomes a product.

The insight was simple: there were parts of the UK where demand for Chinese food was strong, but supply on the platform was thin. Deliveroo had the data to see it. What it needed was someone to build a commercial strategy around the gap and execute it.

I led the overall strategy and built the team to deliver it. Two managers based across the UK and Ireland, focused exclusively on Chinese restaurant acquisition, identifying supply gaps through data analysis, targeting the right areas, and going after the restaurants that would move the category. Premium, high-end Chinese restaurants were a priority because of the average order value impact and the signal it sent to consumers about the quality of the category.

Exclusivity was central to the commercial approach. These were not restaurants you could sign with a standard rate card; they had relationships, reputations, and choices. I managed the senior relationship development and set the commercial framework that gave the team the tools to close.

Leading a small, focused team on a clear commercial mandate is something I find energising. The combination of data-driven diagnosis, relationship-led execution, and structured team management is a pattern I have replicated in different forms across different businesses.

There is a version of commercial leadership that is entirely outward-facing: managing partners, closing deals, driving revenue. And then there is the less visible work: making sure the team behind you has the tools, knowledge, and accountability structures to operate at a higher level. I did both.

At Deliveroo, I owned the commercial enablement stack for the UKI team. Showpad was the knowledge management and presentation layer: a central repository for internal and external content that the commercial team could access and use in partner conversations. My job was to drive adoption across a large, distributed team by making it genuinely useful: the right content, easy to find.

Salesforce was the commercial operating system. CRM hygiene, pipeline integrity, accurate stage progression, senior management reporting. I held the team accountable for keeping their pipelines clean and reported back to leadership on commercial performance across the UK and Ireland. The numbers are only useful if the data behind them is trustworthy.

Roo Academy was the learning layer. Working with a colleague, I helped build and deliver an internal learning platform with gamification mechanics to drive engagement. The curriculum covered commercial skills, negotiation, data interpretation, and operational knowledge. I presented new courses and embedded the culture of continuous learning that a fast-scaling commercial team needs.

Most candidates at my level have built revenue. Fewer have built the infrastructure that makes a revenue team systematically better. That is a different skill, and one I am proud of.