In an era where business leaders are inundated with automated emails, generic sales pitches, and AI-generated messages, earning the attention of decision-makers has become one of the greatest challenges in modern commerce. While technology has made outreach faster and more scalable, it has often done so at the expense of authenticity, relevance, and trust.

Recognising this challenge, Rich Cronin, Co-Founder and CEO of Outpilot AI, set out to redefine how organisations build meaningful commercial relationships. Drawing on more than 25 years of experience across management consulting, enterprise sales, and elite sport, Cronin recognised that successful outreach is not about volume; it is about credibility. Together with Co-Founder and CTO Tanmay Sharma, he developed Outpilot AI, a platform designed to help organisations identify the right opportunities, reach the real decision-makers, and initiate conversations that feel genuinely human.

Since its launch in 2026, Outpilot AI has gained traction among elite sports organisations, global brands, sponsorship rights holders, and complex B2B enterprises across multiple continents. Supported by an advisory board that includes Reebok Co-Founder Joe Foster, the company is demonstrating how artificial intelligence can enhance, rather than replace, human judgement.

In this exclusive interview with Global CEO Magazine, Rich Cronin shares the vision behind Outpilot AI, the lessons learned from elite sport, and his perspectives on the future of intelligent commercial outreach.

1. After more than 25 years across consulting, commercial development, and elite sport, what inspired you to establish Outpilot AI, and what critical market gap were you determined to solve?

The honest answer is frustration born from repetition.

Over more than 25 years, I led senior commercial outreach across management consulting, enterprise sales, and elite sport. I founded and ran my own management consultancy for a decade, working with global brands and building senior relationships across complex enterprise environments. I have also led commercial strategy and sponsorship acquisition in professional sport via a sports agency. In every one of those roles, the same pattern kept appearing.

The most valuable relationships I ever built started with a single message that demonstrated genuine understanding of the person, their organisation, and the specific opportunity. That kind of outreach works. It opens doors that templated emails never will. The problem is that it does not scale. Writing ten of those messages a day is achievable. Writing two hundred is not. And for any commercial team with serious growth ambitions, that ceiling becomes the bottleneck.

What I watched happen over the last decade is that most technology tried to solve this by going in the opposite direction. Platforms emerged that could send thousands of emails, but they stripped out everything that made outreach effective in the first place: judgement, tone, context, and credibility. They tried to scale outreach by flattening judgement into templates or weak AI personalisation. The result was more volume and worse outcomes. Senior decision-makers learned to delete these messages within seconds.

My co-founder, Tanmay Sharma, who has worked with some of the most respected companies in AI, and I built Outpilot to solve that tension properly. The platform is an always-on commercial engine that identifies the right organisations, surfaces the right decision-makers, and produces genuinely human outreach at scale without sacrificing credibility. In early trials, we secured senior-level conversations in environments where generic outreach simply does not get a response, including elite sport and complex enterprise.

The gap in the market was never about sending more messages. It was about sending better ones, at scale, without compromising the quality that earns trust.

2. How does Outpilot AI help organisations identify real decision-makers within complex businesses, particularly when influence often extends beyond formal job titles?

This is one of the most misunderstood problems in commercial outreach, and one of the reasons so much of it fails.
Most platforms rely on job-title matching. They search for “Head of Partnerships” or “CMO” and assume that the person with the title is the person who controls the decision. In practice, that is frequently wrong. Influence inside complex organisations is distributed and often invisible from the outside.

We describe this layer of the platform as decision-maker intelligence. Rather than simply scraping a title from a database, Outpilot surfaces the individuals who actually influence sponsorship and partnership decisions, going beyond job titles and organisational charts. The platform analyses an organisation’s structure, recent activity, strategic priorities, and public signals to build a more accurate picture of where real decision-making authority sits. That might mean identifying a regional VP who controls budget independently of the global CMO, or recognising that a newly appointed Director of Strategy is the actual gatekeeper for partnership decisions, even though their title would not appear on a standard target list.

Alongside that, our research-led targeting capability identifies organisations that genuinely align with a client’s commercial strategy, not just the most visible or over-targeted names. These two layers working together mean our clients are reaching the right person at the right company with a message that is specifically relevant to them.

The practical impact is significant. Our clients are seeing a 90% reduction in outreach research time and ten times more qualified conversations per month. When you reach the right person with the right message, response rates increase dramatically and conversations start at a higher level. When you reach the wrong person, even a perfectly written message goes nowhere.

3. Many executives are overwhelmed by generic automated outreach and AI-generated messaging. How does Outpilot ensure communication remains credible, relevant, and genuinely human?

This is the central question that defines our entire approach.

The market is flooded with tools that claim to personalise outreach using AI, but most of them do something closer to mail merge with a few variables swapped in. They insert a company name, reference a recent LinkedIn post, and call it personalisation. Senior decision-makers see through this immediately because the structure, rhythm, and reasoning of the message still feel automated.

Outpilot works differently because it was built by operators, not marketers. I spent decades writing high-stakes outreach by hand, sitting in rooms where a single email to the wrong person in the wrong tone could close a door permanently. We understand what makes a message earn a reply. It is not simply mentioning something the recipient did recently; it is demonstrating that you understand their strategic context, why an opportunity is relevant to them specifically, and what makes the timing appropriate.

Every message Outpilot generates is bespoke. There are zero generic templates. The platform researches each prospect individually, considers their organisation’s current position, and constructs email and LinkedIn messaging that matches the client’s tone and regional voice, grounded in real commercial, market, and brand context. It reads as though it was written by a senior commercial professional who took the time to understand the opportunity before making contact.

That is not a marketing claim. Beukes Cremer, Commercial Manager at Brasil Rugby Union, described it as a “commercial machine on steroids”. Adam Behnke, Chief Operating Officer at Brooklyn Pickleball, reported that Outpilot helped them secure their first partnership in under seven weeks, a process that typically takes months.

Joe Foster, Co-Founder of Reebok and one of our advisers, put it well when he said that what impressed him about Outpilot is how human the outreach feels and that it understands tone, context, and brand in a way most tools simply do not. That is the benchmark we hold ourselves to every day.

4. Outpilot was first proven in elite sport, where trust, reputation, and brand risk are extremely sensitive. What lessons from elite sport have most influenced your business philosophy and communication strategy?

Elite sport taught me three things that now sit at the foundation of everything we build.

The first is that credibility is binary. In sport, when a professional club reaches out to a potential sponsor, the first message either earns a conversation or it does not. There is no second chance to reframe a poor first impression. If the approach feels generic, low-effort, or tonally wrong, the door closes permanently.

That reality forced me to develop an almost obsessive attention to how outreach is constructed, not just what it says, but how it feels to the person receiving it. Outpilot was built with that same standard, and it is why organisations operating in the most sensitive commercial environments trust us, from Premier League football clubs to Brooklyn Pickleball, a Major League Pickleball franchise backed by some of the biggest names in American sport and entertainment.

The second is that relationships are the product. In elite sport, commercial success is not driven by transactions. It is driven by long-term partnerships between rights holders and brands, built on trust, alignment, and mutual value. The outreach that initiates those relationships has to reflect that ambition from the very first touchpoint. You cannot build a partnership worth millions on the back of an automated template. That philosophy now guides how we serve B2B enterprise clients too, because the dynamics are identical at the senior level.

The third lesson is that reputation compounds. In sport, every piece of communication you send reflects on the institution behind it. A poorly judged email does not simply lose a deal; it damages the brand. This is why sports organisations are among the most demanding clients when it comes to outreach quality.

Proving Outpilot in elite sport first gave us an extraordinary foundation. If the platform performs to the standard required by professional sport, it is more than capable of serving any commercial environment where credibility and tone determine outcomes.

5. As artificial intelligence continues to reshape business development and stakeholder engagement, how do you envision the future of intelligent outreach evolving over the next five years?

I believe we are at the beginning of a fundamental shift in how businesses initiate commercial relationships, and the organisations that understand this early will have an enormous competitive advantage.

Over the next five years, the volume of outreach will increase dramatically as more businesses adopt AI tools. But that actually makes quality more important, not less. When every inbox is flooded with AI-generated messages, the ones that stand out will be those that demonstrate genuine understanding, strategic relevance, and human judgement. The companies that use AI to send more noise will see declining returns. The companies that use AI to send fewer, better, and more precisely targeted messages will dominate.

We are already seeing this with our own clients, where Outpilot has delivered four face-to-face meetings within 48 hours of going live because the outreach is precise enough to generate meaningful conversations immediately.

I also expect to see a convergence between outreach intelligence and relationship intelligence. The platforms that win will not simply help you send a great first message. They will help you understand who to contact, when the timing is right, what strategic context makes an approach relevant, and how to build a sustained engagement strategy across multiple touchpoints.

Outpilot is already moving in this direction. Our vision is to become the default growth engine for sponsorship acquisition in modern sport and, from there, redefine how complex B2B pipelines are built everywhere.

Perhaps most importantly, I think the next five years will separate AI companies that understand commercial reality from those that are simply riding a technology wave. The businesses that will thrive are the ones built by practitioners who have lived the problem they are solving, not just engineers optimising for engagement metrics. Outpilot was built from inside the commercial function by people who spent decades doing the work themselves. That practitioner-led DNA will become the defining advantage in this space.

Our current client base already spans elite sports organisations globally, NFL teams, Premier League clubs, professional rugby federations, Major League Pickleball franchises, high-profile events, and B2B enterprise organisations. The common thread is that these are organisations where the quality of the first conversation determines whether a relationship is possible. That will not change in five years. If anything, it will become even more true. And that is exactly where Outpilot is positioned.

Company Profile
Commercial Outreach Infrastructure for Elite Sport and Complex B2B

Outpilot AI is commercial outreach infrastructure purpose-built for high-value environments. The platform finds the brands others miss, identifies who actually decides, and writes outreach that sounds like your best person. One platform covering research, qualification, decision-maker intelligence, personalised outreach, and campaign reporting.

The talent inside commercial teams is not the bottleneck. The infrastructure is.

Research takes hours per prospect. Contact verification is often unreliable. Each quality email takes 20 to 30 minutes. And by the time you reach the right person, competitors have already been in their inbox. Outpilot removes that bottleneck entirely, giving commercial teams the ability to generate volume without losing the credibility, tone, and judgement that make outreach effective at the senior level.

AI does the work. You make every decision. Nothing is sent without approval. When a prospect replies, the AI stops. Replies are routed to your real inbox. You take over as a human. Outpilot books the meeting. You own the relationship.

Founders

Rich Cronin, Co-Founder & CEO: More than 25 years across management consulting, enterprise sales, and elite sport, including founding and running his own management consultancy for a decade and a sports agency. Having spent years writing high-value sponsorship and B2B outreach himself, he understood that scaling it almost always destroys quality. He co-built Outpilot to give commercial teams the precision of a bespoke approach at the speed and scale modern pipelines demand.

Tanmay Sharma, Co-Founder & CTO: World-class AI expertise shaped by years of building at the cutting edge of Silicon Valley. From training more than 160,000 people in applied AI to engineering systems used by thousands of companies, he has operated at the intersection of AI and growth since before it became mainstream. At Outpilot, he owns the entire technology stack behind the platform’s campaigns.