Interview with Tom Wiseman - Digital Project Manager at Osprey London

Hi Tom, You are Digital Project Manager at Osprey London. Can you tell us a little bit more about yourself and your background?

My first experience in e-commerce came in my previous role before joining Osprey London, where I managed a portfolio of DTC and retail fashion and beauty brands at an agency specialising in paid media and creative strategy. This role provided me with exposure to a diverse range of brands, each with different product types, channel mix and markets. It allowed me to develop a broad understanding of the challenges and opportunities brands face in an evolving digital landscape.

As the client base and team expanded, accelerated by COVID, I transitioned into a more strategic role, leading strategy and data across our entire portfolio. My focus was on building out our data solutions and leading marketing strategy to enable us to surface insights across our client base enabling our teams and clients to cross pollinate successful strategies and tactics to drive growth through their digital marketing activity.

While I enjoyed the marketing side, I was eager to expand my expertise beyond media and gain a deeper understanding of the processes and systems that drive e-commerce and retail operations. This led me to join Osprey London as a Digital Project Manager nine months ago, at a pivotal moment when the brand was starting a digital transformation to replatform and redesign its website. This role has provided the perfect opportunity to deepen my knowledge of e-commerce and the systems that provide an immersive and seamless customer experience.

Besides doing a big replatforming and redesign project just recently, what does a typical day at Osprey London look like?

What I love about my role is that two days are ever the same. Since completing the recent replatforming, we now have a strong foundation in place to further enhance the customer experience with new features, expand into new markets and channels, and improve functionality. I work closely with our founders and internal stakeholders to understand the business vision and requirements, translating them into plans within our systems and tech stack. A key part of my role involves collaborating with our frontend agency, Grebban, and our integration specialists, Frog Stack, to scope project requirements, manage sprints and plan our roadmap to ensure we are prioritising features which will have the most significant impact. Beyond managing web projects, I’m also involved in broader business initiatives, including our integration with Sitoo to enable improved omnichannel features, marketplace integrations, and the development of our internal BI tool and reporting systems to automate insights and improve decision making across departments.

This is my first e-commerce role where I’ve worked hands-on with these systems, and while it has been a steep learning curve, the constant learning is both challenging and rewarding.

Looking back 6 months ago, we started our replatforming project together for Osprey London’s new flagship store. Talk us through the discovery phase and the first weeks.

The discovery phase was crucial in laying the foundation for the project. We worked closely with Grebban to define our vision and ensure alignment on the direction we wanted to take.

Our head office is located on a beautiful estate in Hertfordshire, and having Grebban visit us in person was invaluable. It allowed them to gain a deeper understanding of our founders, Graeme and Alex, as well as immerse themselves in our offices, an environment that reflects our brand’s identity and the experience we aim to create digitally. We also took them to our St Albans store to provide a complete view of the business, helping them fully grasp the connection between our physical and digital presence.

Following this, we worked closely with Grebban to align on our goals and map out the ideal customer journey. A major focus was creating a digital experience that tells our brand and product story, enables product discovery, and goes beyond a simple product catalog to deliver a truly immersive brand experience.

Through a series of workshops, we scoped out our requirements, prioritised them, and worked collaboratively with Grebban as they translated these into design batches before development began. Every stage of the process was carefully planned by the team at Grebban, ensuring the project stayed on track and delivered on our vision.

Some might say the timeline was tight; however, a typical replatform project with us and Centra takes about 6 months. In terms of the timeline, what way of working examples do you want to share?

Yes, six months is a fast-paced timeline for a project of this scale, but a combination of expertise, planning, and efficient processes was key to meeting the deadline. Our agencies Grebban and Frog Stack played a crucial role in ensuring a smooth execution. It was essential for us to hit this deadline so we could launch ahead of the peak Q4 trading period, allowing time to refine the site before traffic increased.

We worked in sprints, focusing on iterative progress rather than trying to tackle everything at once. We started with design batches, incorporating regular feedback loops to align on any necessary adjustments before each section moved into development. This approach ensured steady progress while keeping the project on track with key milestones.

Regular check-ins with all stakeholders allowed us to identify and resolve issues quickly, preventing blockers. Clear communication and alignment between Osprey London, Grebban, Frog Stack, and Centra was one of the biggest factors in staying on schedule.

Lastly, a major contributor to the project’s success was the talented team at Grebban. We had an great working relationship, with direct communication and timely responses from their team. They consistently went above and beyond to ensure the project was a success, and their dedication played a crucial role in delivering the site on time.

What has surprised you most during these 6 months?

Coming from a marketing background, I initially believed that growth was primarily driven by marketing efforts. While marketing is essential for building awareness and generating demand, I soon realised that various factors across the digital and omni-channel experience can significantly impact performance. These elements work together to create a halo effect, amplifying the effectiveness of marketing and maximising overall results. A good analogy is a car engine, no matter how much fuel you provide or how quality that fuel is, if the engine isn’t running at optimal condition, the car’s performance will fall short. Similarly, without optimising the underlying systems and infrastructure, even the best marketing efforts won’t deliver their full potential.

One of the biggest surprises was the immediate improvement in performance. I expected a temporary dip due to the complete change of both our back-end and front-end systems. However, the enhancements in site speed, navigation, product discovery, and overall convenience significantly boosted performance from the outset. This reinforced the value of the replatforming, benefiting both the brand and our customers.

Thankfully, there were no unexpected surprises during the project itself. As the launch approached, I naturally felt nervous, both about how customers would receive the new website and how it would be perceived internally, given its importance for Osprey London. The response was overwhelmingly positive from both customers and the internal team.

As the project owner, what was your initial vision for the re-platforming, and how did you define success for this project?

Our vision was twofold. First, we aimed to move beyond being just a digital catalogue by creating a more immersive experience. This involved incorporating high-quality imagery and video to showcase our products, telling compelling brand and product stories to bring them to life, and enhancing product discovery with features that make it easier for customers to explore and engage.

Second, we wanted to transition to a composable tech stack that would allow us to leverage best-in-class software to deliver an exceptional customer experience while also streamlining back-end operations. For a smaller team, efficiency is crucial, so having more flexible and scalable solutions was a key priority.

When measuring success, we focus on both quantitative and qualitative performance metrics. Key indicators such as conversion rates, average order value, site speed, and customer engagement to name a few help us assess how functional and optimised the site is. However, these metrics don’t always tell the full story. It’s important to gather qualitative feedback from customers through our on-site form or direct interactions to understand what they like, identify pain points, and determine areas for improvement.

One of our major objectives is improving product discovery, as traffic often flows directly to the homepage or product description pages (PDPs). To assess progress, we analyse the distribution of traffic across products and ranges to see if customers are engaging more broadly with our catalogue.

Lastly, while it may not be as glamorous, operational efficiency is just as critical for our growth ambitions. Ensuring we can bring products, campaigns, and expansions to market faster is a key success factor in our re-platforming efforts.

What were the biggest priorities from the outset, and did they shift or evolve as the project progressed?

Our biggest priority was to establish a solid foundation for our new digital flagship while ensuring we could go live ahead of the peak trading period. Careful planning and regular communication were key in keeping the project on track and minimising delays.

Fortunately, due to this structured approach, we remained aligned with our initial goals. There were no significant shifts in scope, and we successfully achieved everything we set out to accomplish from the outset.

How did you coordinate efforts between Osprey’s internal team and Grebban to ensure a cohesive project direction?

In addition to our initial workshop to define the vision and requirements for the new site, we held regular scoping sessions to ensure we remained aligned with the project plan and timeline, while addressing any changes, dependencies, and blockers.

Throughout the project sprints, we had weekly calls with relevant stakeholders to track progress, review feedback, and discuss testing. This regular communication helped keep everyone on the same page and ensured that any issues were dealt with promptly.

We used Asana to centralise project requirements, monitor tasks, and maintain accountability across all teams. This helped us stay organised and ensure nothing was overlooked.

Grebban and our other partners were extremely responsive when challenges arose and proactive in offering solutions, which was instrumental in keeping the project on track and running smoothly.

What were some unexpected lessons you learned about managing a project of this scale

One of the biggest lessons was realising just how much work and expertise go into creating a digital experience. There are lots of moving parts, and every decision, especially around tech selection and feature prioritisation has implications on long term ambitions. Thorough research is essential to making the right decisions, as these choices directly impact not only the website’s capabilities but also the long-term goals of the entire business.

While not entirely unexpected, this project reinforced the importance of sticking to project management fundamentals including planning, testing, and regular reviews. These steps are essential to minimising surprises and keeping the project on track. Given the interdependence between tasks, getting input and alignment from all stakeholders early on was critical. Ensuring everyone was on the same page helped ensure all aspects of the project were covered.

What advice would you give to other brands considering a re-platforming project?

The first and most crucial step is to clearly understand your business needs. Take the time to thoroughly assess your requirements and ensure that the platform and tools you choose align with your overall goals. While it can be tempting to include every possible feature on your wishlist, not everything will be relevant to your brand or product offering.

Loyalty programmes are a prime example, many assume that rewarding loyalty must involve points or financial incentives. However, this approach may not align with your brand values or resonate with your customers, especially if your brand prioritises sustainability, as financial rewards could be perceived as encouraging overconsumption.

Loyalty doesn’t always need to be tied to financial incentives, it could instead offer access to exclusive products, invitations to special events, or enhanced delivery benefits. Understanding your customers is crucial to building an experience that not only meets their needs but also surprises them with unexpected, meaningful rewards.

One of the key advantages of a headless solution is its inherent flexibility, allowing you to design an experience and proposition that are truly unique and tailored to reflect your brand’s values and objectives.

If you are new to Centra, it’s worth investing time early on to familiarise yourself with the platform. Developing a strong understanding of its capabilities will help you avoid delays during implementation. Leveraging Centra’s documentation and support will provide valuable guidance to keep your project on track.

Thorough testing is critical to ensuring a smooth launch. Conducting testing across all possible scenarios and use cases will help minimise post-launch issues. Launching a BETA version as early as possible allows time before the official go-live date to identify and resolve any potential bugs or challenges.

Finally, maintaining strong communication throughout the project is crucial. Engaging all stakeholders from the outset and ensuring regular check-ins will help prevent potential blockers and keep the project aligned with the original goals. Clear and frequent communication ensures everyone stays on the same page, making it easier to address issues proactively and deliver a successful replatforming project.

How did you approach the migration of data, content, and customer information to ensure accuracy and continuity?

The replatforming project provided the perfect opportunity to clean and enhance our product data within our ERP, ensuring that we could enrich products on the frontend and enable the new features we planned to launch on our website.

For customer data, while historical data remains within our ERP, we chose to invite customers to create a new account in the “My Account” section, allowing them to update their passwords securely.

Close collaboration with our integration partner and Grebban was key to mapping data accurately, ensuring that all necessary information was present in Centra’s backend to deliver the desired frontend experience.