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In Profile: Richard Rosenberg at Spendesk

Small and medium-sized companies (SMEs) often struggle with managing expenses, which can be a complex and time-consuming process. Traditional finance software can be outdated and difficult to use, and reconciling expenses can involve sifting through stacks of receipts and invoices.

We sat down with Richard Rosenberg, chief product and technology officer at Spendesk, an expense management solution for SMEs across Europe. Its software combined with smart payment cards provides finance teams with complete transparency and control over all payments, while increasing productivity and collaboration of operational teams.

With extensive experience in software leadership roles, including CTO at Financial Times, Hotwire and, Rosenberg is a driving force behind the success of Spendesk. We discuss his journey into the fintech industry, the challenges facing the sector, and what’s next for the company. 

Richard Rosenberg, chief product and technology officer at Spendesk
Tell us more about your company and its purpose

Spendesk is a seven-in-one spend management solution used by thousands of small and medium-sized businesses; from start-ups to established brands. From the beginning, our mission has been to use technology to democratise the power of data.

By allowing finance teams to make smarter decisions, our digital solution incorporates company cards, expenses, invoices, accounting, approvals, budgets, and spending reports as one simplified stack. Our spend management and analysis software simplifies the work of finance professionals, allowing them to execute the pressing business needs of their company, rather than being bogged down by tedious manual tasks and spreadsheets.

What are some of your recent achievements you’d like to highlight?

From a technology perspective, I am most proud of our engineering culture here at Spendesk, and how we have evolved on our journey from startup to scale up and beyond; trying to keep what is great about a small company but adding on the requirements of a larger company.

In practice, this has meant growing the team, in size and seniority, and accelerating our delivery capabilities. At the same time, we have kept our product performant and secure as we grow our customer base.

It is all about sustainable progress for me, ensuring there is a balance between engineering foundational work and adding product features without overextending.

How did you get into the fintech industry?

My journey into fintech was perhaps not a normal one. I have worked in numerous industries and on many different challenges, but the common theme is looking at how software can change behaviours and create products that look at day-to-day problems and solve them in a multitude of ways.

Working at the Financial Times gave me exposure to and understanding of the industry in general, but fundamentally I was attracted to the Spendesk product, and the Spendesk team. I thought that this would be a place where I could really add value and have impact.

What’s the best thing about working in the fintech industry?

As I touched on in my previous answer, the reason I am in the role of group product and technology officer is because I love looking at problems that people or industries face, and seeing how software can solve these problems and change the behaviours around them. This has been true in all of the industries I have worked in – from changing how people watch TV to how they get their news content.

However, in the fintech industry you get to deal with interesting problems that are core to how companies work, and quite often are problems that have been solved the same way for years and are ripe for a bit of disruptive thinking.

What frustrates you most about the fintech industry?

I may not have been in the industry long enough to see the real frustrations that people feel about fintech. I am a person who likes to challenge the status quo and question things, so I assume that I will soon get frustrated at how difficult it is to change certain areas of business.

How have your previous roles influenced your career?

I have learned three very specific lessons. First, in my previous software development role for Sky, I learned how to really understand the customer, and how crucial it is to have an agile engineering process that creates and operates fantastic products.

At Expedia, I learned about the challenges of ecommerce on a global scale. For example, understanding the differences between a Japanese and South Korean homepage. It also became clear that really appreciating the power of your data, and how it can be used to make better decisions through features like artificial intelligence (AI) and machine learning (ML) can be so powerful.

Finally, at the Financial Times I learned the importance of a great working culture and just what can be achieved by empowered teams on a mission.

What’s the best mistake you’ve ever made?

There is a story that I always come back to regarding a mistake made back at Sky. There was a complicated technology program that was under immense internal pressure from a delivery and timeline perspective. This pressure led us to take a risk and upgrade a key system before a big sporting event, to preserve a plan.

The new system failed, and this massively affected our customer’s ability to use our product and watch TV. This was a very difficult learning, but it has shown me to always prioritise and protect the needs of the customer, and it is always better explaining a delay to your bosses and stakeholders rather than explaining a catastrophic failure.

SpendeskWhat has the future got in store for your company?

At Spendesk, we will continue to work hard to free employees from the time-consuming processes of expense management at work, so that they can concentrate on their core business. We have several features we are developing, and we look forward to sharing them with you in the coming months.

What are the next key talking points or challenges for your industry as a whole?

The two key topics that have been at the forefront from my perspective are data privacy and generative AI. When thinking about data privacy, I can’t help but imagine great opportunities for companies that are open and transparent about data collection and usage practices, and that give customers more control over their data. These opportunities can be further enhanced by the use of technology that will benefit both businesses and their customers in equal measure.

With the rise of products like Chat GPT, I’m interested to see how generative AI is going to change different roles. At this point things are unclear exactly how, but the dust cloud is beginning to lift on the potential of generative AI.


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