A Special Feature on Europe’s Most Remarkable CROs – The CIO World.
They say growth is never by mere chance; it is the result of forces working together. Similarly, scaling a business is not just about numbers—it’s about vision, strategy, and the ability to turn data into action. Many companies struggle with growth not because they lack potential but because they lack the right leadership to steer them in the right direction. In the complex and progressive world of SaaS and security intelligence, having the right leader makes all the difference.
Meet Richard May, a name synonymous with strategic scaling and data-driven decision-making. As the Chief Revenue Officer (CRO) of Osprey Flight Solutions, he brings decades of experience in growing SaaS businesses with precision and insight. From developing early SaaS products to leading high-growth organizations, his journey is a testament to innovation, resilience, and a commitment to excellence.
At Osprey Flight Solutions, Richard plays a pivotal role in leveraging AI-powered risk intelligence to enhance aviation security. Under his leadership, the company is redefining how organizations assess and mitigate risks, offering real-time, data-driven insights that make the skies safer. His expertise in revenue growth, go-to-market strategies, and operational efficiency has positioned Osprey as a game-changer in the industry.
In this exclusive interview, Richard shares his thoughts on scaling businesses in today’s competitive landscape, the role of data in driving growth, and his vision for the future of security intelligence. His journey proves that with the right strategy, even the most ambitious goals can become reality.
Joining Osprey Flight Solutions: A Mission-Driven Decision
The CIO World: Richard, can you introduce yourself and share what motivated you to embark on this sector?
Richard May: I am the CRO of Osprey Flight Solutions, a security and geopolitical risk intelligence platform. The decision to join this company was almost instantaneous. After a single meeting with the CEO, I knew I wanted to be part of this journey. What stood out was the passion driving the company—using technology and innovation to make aviation safer and more secure. This commitment is ingrained in the company culture and is something the entire leadership team believes in.
Beyond the mission, I was also captivated by the capabilities of Osprey’s technology. The platform accurately predicts and forecasts geopolitical and security risks, identifying potential civil unrest and conflict flashpoints. In aviation, this intelligence can save lives, but its application extends to any industry exposed to geopolitical or supply chain disruptions. Given the increasing instability in the world today, this level of intelligence is more critical than ever.
Career Journey: From Early SaaS to Commercial Leadership
The CIO World: Can you share your career journey in the SaaS industry?
Richard May: My journey began in the 2000s when I developed a technology solution to support my business. We created an internet-accessible application for clients to manage their assets, though we didn’t initially recognize it as SaaS. Over time, it became clear that the intellectual property (IP) behind the technology was the real value driver. This was the early days of SaaS, before smartphones, and I remember accessing it through my Palm Treo phone—it felt revolutionary.
After exiting that business, I returned to Europe and entered MarTech, becoming the VP of EMEA for a publicly traded Silicon Valley company in their London office. This was an incredible experience. Understanding the structure and dynamics of a leading SaaS company that scaled to over $100 million ARR was invaluable. Managing multiple offices throughout the EMEA region and coordinating with eight offices globally, headquartered in San Francisco, was a steep learning curve but immensely rewarding.
Five and a half years later, I was offered the opportunity to join a UK scale-up that had just secured Series A investment. Once again, I bought into the passion of the founders and could clearly see the value the technology brought to some of the world’s largest advertisers, like Diageo, Heineken, and Ford. What excited me was the opportunity to build a world-class commercial team structured for scale and embark on a high-growth journey. This also gave me my first Chief Revenue Officer role.
After an exciting growth journey, the company became the target of an industry acquisition—an opportunity too good to miss for the founders and investors. Through one of the investor groups, I was introduced to Osprey, another of their portfolio companies.
Scaling Strategies for SaaS Growth
The CIO World: What strategies have you found most effective in scaling businesses, particularly in the SaaS sector?
Richard May: Before scaling, it’s crucial to ensure the foundational elements are in place. Understanding your Ideal Customer Profiles (ICP) and the key people within them is stage one. However, understanding the true value you provide to clients is often overlooked. It’s easy to see why operational users want to use your product and the value they’re looking for, but what are the challenges you solve for the company as a whole? What keeps the C-suite and board up at night, and how do you solve one or more of those challenges?
At Osprey it’s a great example where the core users want intelligence faster and automations to be able to complete their jobs quicker and easier, which results in keeping passengers safer. While this is important, the board is also concerned about costs, fuel burn, and environmental impacts. These objectives are intrinsically linked, but as a vendor, we must help organizations connect the dots. Having a granular understanding of risk—fast, actionable intelligence and reliable forecasts—enables teams to be proactive rather than just reactive when unexpected events occur.
This gives airline operators the opportunity to significantly reduce one of their largest costs: disruption. Every time a flight is diverted, delayed, or canceled; the costs are significant. The ability to mitigate or avoid these disruptions through proactive management is one of the few levers airlines can use to truly reduce costs.
Additionally, having a granular, reliable view of risk enables other operational optimizations. One operator told us that after only a few months with Osprey, they had calculated £1.2 million in fuel cost savings by identifying more efficient, safe routes. Understanding where risk isn’t is just as valuable as knowing where it is.
Once board-level value is understood, quantified, and validated by clients so your teams can sell to both the C-suite and end users, it’s crucial to establish a clear, repeatable process. One of the most common mistakes in sales, particularly in complex enterprise sales, is not recognizing where the prospect is in their purchasing journey.
This often leads sales teams to complete activities simply because it’s the next stage in their sales process, without confirming whether the buyer is at the right stage to receive that information. Establishing a clear process with defined actions and requirements at each stage allows teams to scale with reliable, predictable growth.
Of course, creating a predictable sales machine is only part of the equation—you also need to retain and grow clients. Otherwise, you’re running through sand with a leaking bucket. Understanding the customer lifecycle, segmenting customers, managing each segment with appropriate resources, and having clear playbooks for every stage of customer evolution lay the foundations for scaling as ARR accelerates.
At Osprey, we’re fortunate to have an incredible Head of Customer Success who ensures everything runs smoothly. However, it’s also a testament to the product itself that we maintain tremendous client retention metrics. Last year, in our top ICP segment, we achieved over 99% Gross Revenue Retention—demonstrating just how successfully we’re solving major challenges for our clients.
Building a Data-Driven Culture
The CIO World: How do you build a data-driven culture to support growth?
Richard May: For me, the first stage is ensuring you have the right commercial architecture in place. You need to know what to measure, how to measure it, and how to leverage the tech stack at your disposal to have the right metrics at your fingertips at any moment. It’s not effective if you have to rely on finance to calculate the metrics you need and only receive them periodically.
Secondly, you need a clear process that encourages consistent, reliable data input so that your data is comparable, can be modelled, and is therefore valuable. For example, pipeline growth is a critical metric for any commercial leader to track. However, the value of the pipeline is typically input manually by team members. If they are overly optimistic and assign a much higher value to an opportunity than reality dictates, you end up with an inflated pipeline that is not as valuable as it appears—ultimately leading to poor forecasting and potentially poor investment decisions.
Having a clear process for determining the value that should be assigned to an opportunity when it qualifies helps prevent this pitfall.
Indicators of a Successful Go-to-Market Strategy
The CIO World: What key indicators define a successful go-to-market strategy?
Richard May: Early indicators include pipeline growth, deal progression, and win rates. Looking further back, marketing metrics play a crucial role. Are we seeing the expected level of qualified pipeline from each of our marketing activities? Are we getting the expected engagement through our partnerships, etc.?
However, I believe unit economics ultimately determine the success of go-to-market strategies. If you have strong ARR and revenue growth metrics, what are your acquisition costs? How long does it take to recoup the cost of acquiring a customer? What are your retention metrics? How long does the average client remain a customer?
For me, Net Revenue Retention (NRR) is the ‘gold standard’ of metrics because it not only measures client retention but also revenue growth from existing customers through increased usage and the adoption of additional products. This demonstrates a perfect fit in solving critical challenges. In 2024, Osprey achieved a 116% NRR, underscoring the value it delivers to clients and how mission-critical it has become.
That said, just like with any data-driven strategy, granularity is key. You need to have these metrics for each of your Ideal Customer Profile (ICP) target segments. Relying solely on overall ‘average’ metrics can be misleading and could result in poor decision-making.
Leadership, Mentorship, and Company Culture
The CIO World: What role does mentorship play in your leadership style, and how have you benefited from it throughout your career?
Richard May: I think mentorship is critical. I’ve been fortunate to have several key mentors throughout my career who have helped me both professionally and personally. I’d like to think I’ve also been a mentor to many members of my teams over the years, and I certainly encourage everyone to seek out a mentoring relationship with someone they feel can support and guide them.
I’ve been fortunate to have several team members who have chosen to trust me and join my teams a second and even a third time, which I hope indicates that I’ve been able to create an environment that promotes personal development and growth.
Once, I even had someone I turned down for a job reach out to me, asking if I would be their mentor. I really respected that, and we met regularly for quite some time. Now, he has a flourishing business promoting sustainability, which is a great success story.
Ultimately, whether it’s mentoring, coaching, or simply engaging with peers through professional cohorts and communities, we all need to continually develop, learn, and grow. I also believe that in these situations, you get out what you put in. I’ll always be happy to take the time to talk to others, share my knowledge, and hopefully help them avoid some of the lessons I had to learn the hard way!
Balancing Growth and Culture
The CIO World: How do you balance growth goals with maintaining a healthy company culture?
Richard May: This question suggest the two outcomes are at odds, whereas I fully believe they are intrinsically linked. Success comes when your engine and all the parts of the machine are working in harmony and with purpose. My experience suggests growth goals are achieved through teamwork and collaboration. A key phrase we use at Osprey is ‘We win together and we lose together’. As long as the team did everything they could, leveraging all the support and tools they have available to them, we don’t dwell on the losses. We will analyze the outcome and process, and If in hindsight there’s something we could/should have done better, then this is the takeaway and we learn from it. When everyone understands this I find cross team communication, alignment and cooperation increase which leads to better results and achieving those growth goals.
The CIO World: With the challenges of the business world, how do you maintain consistency?
Richard May: Business—and the commercial side of business—always has its ups and downs. I often compare it to surfing it feels amazing when you’re on top of the wave, and you should enjoy it and try to stay on it as long as you can. However, you will inevitably fall off at some point, and this can really hurt. The trick is to get back on the next wave as quickly as possible, which takes an incredible amount of effort—especially when you’re emotionally drained, possibly doubting yourself, and struggling to see the immediate results of your efforts. This is something we all must deal with in a commercial role. The more senior you get, the greater the pressure, the more it impacts the business, and the harder it hurts when you fall off the wave.
I’ve found that creating the right structure, processes, and measurements—like those we’ve already discussed—helps keep the business riding the wave much longer. These elements act as early warning indicators, allowing you to address issues before they become problematic.
However, when things do go wrong, you can have confidence that all key indicators are healthy. This, in turn, enables you to reassure your board and leadership stakeholders that your forecasts remain strong and that this is just a temporary setback. With this confidence, you can then analyze all stages of the process to identify any deviations. Nine times out of ten, when performance dips, it’s due to a minor process issue that can be quickly addressed.
Advice for Aspiring SaaS Leaders
The CIO World: What advice would you give to aspiring leaders in the SaaS industry?
Richard May: Master the fundamentals before accelerating your career. Too often, I see people eager to climb the ladder without fully understanding the foundations. Whether in sales, operations, or leadership, gaining deep expertise at each stage will make you a stronger leader in the long run.
Also, build a strong network. I’ve been part of Pavilion, a revenue collective, for years, and it has significantly shaped my career. Engaging with peers, learning from others, and staying updated on best practices is invaluable.
Conclusion
Richard May’s journey, from pioneering early SaaS solutions to leading commercial operations at Osprey Flight Solutions, demonstrates how passion-driven innovation, data-driven strategies, and a commitment to mentorship can drive exceptional commercial success. As he continues to scale Osprey and help redefine risk intelligence, his insights offer a roadmap for aspiring leaders looking to make an impact in the SaaS and security intelligence sectors.
