"Outpilot AI helped us land our first partnership in under 7 weeks, what typically takes months. Proud to partner with such a forward-thinking team opening doors for Brooklyn Pickleball."
Adam Behnke
Chief Operating Officer, Brooklyn Pickleball Team
"Outpilot is the first AI solution I've found that's truly tailored for sponsorship, not SAS. No slop, just copy that gets cold outreach opened because it makes the recipient feel known."
Larry Weil
President and Founder, The Sponsorship Guy
Official AI Outreach Partner for
Brooklyn Pickleball Team
Tomorrow City
Precision outreach for sponsorship and complex B2B
An always-on commercial engine that produces genuinely human outreach at scale.Outpilot is an always-on commercial engine that identifies the right organisations, the right decision-makers, and produces genuinely human outreach at scale, without sacrificing credibility.
It is a commercial machine on steroids. Really, really great!!
Beukes Cremer
Commercial Manager · Brasil Rugby Union
“
Outpilot is the first AI solution I've found that's truly tailored for sponsorship, not SAS. No slop, just copy that gets cold outreach opened because it makes the recipient feel known.
Larry Weil
President and Founder, The Sponsorship Guy
“
I rarely recommend tools, but Outpilot AI delivered qualified sponsor conversations faster than expected. It feels less like a platform and more like an extension of your team.
Alex Gingold
Partnerchef · Kungsted Solar Capital
“
Outpilot AI helped us land our first partnership in under 7 weeks, what typically takes months. Proud to partner with such a forward-thinking team opening doors for Brooklyn Pickleball.
Adam Behnke
Chief Operating Officer · Brooklyn Pickleball Team
Senior decision-makers have always expected relevance from the first message.
The landscape hasn't changed. The tools have failed.
What has changed is that most modern tools try to scale outreach by flattening judgement into templates or weak AI personalisation.
Outpilot was built to solve that problem properly.
Our Partners
Built for the world's most ambitious organizations
We're the official AI outreach partner for organizations redefining their industries.
Brooklyn Pickleball is a Major League Pickleball team based in New York, competing in one of the fastest-growing professional sports globally. Backed by high-profile owners including Odell Beckham Jr., Eva Longoria, Cliff Avril, and Tara and Hunter Fieri, the team sits at the intersection of sport, entertainment and brand partnerships. Outpilot supports credible sponsorship outreach around that growth.
Tomorrow.City USA is a high-profile event focused on sport, technology, infrastructure and economic development. The event brings together sports franchise owners including Miami Dolphins Stephen Ross, Sacramento Kings Owner Vivek Ranadive and CEOs from global brands.
Features
Everything you need to dominate your market.
Outpilot provides the intelligence and scale you need to turn cold prospects into warm
conversations.
Precision Targeting
Research-led targeting
Identify organisations that genuinely align with your commercial strategy, not just the most visible or over-targeted names.
Sponsorship teams at professional clubs, leagues, and governing bodies who need to reach brands that genuinely align, not just the usual suspects.
4
Face-to-face meetings booked in 48 hours
90%
Reduction in outreach research time
Senior B2B teams
Partnership, BD and growth leaders at enterprise and mid-market organisations running complex deals where trust and credibility decide outcomes.
10x
More qualified conversations per month
0
Generic templates. Every message is bespoke.
About Us
We are operators,not marketers.
Outpilot was created by operators with over two decades of experience inside sponsorship and
senior commercial dealmaking.
It exists because generic outreach fails in environments where credibility, tone and judgement
decide outcomes.
0+ Years
of experience in elite sponsorships & complex B2B sales
Our Mission
To give organizations a faster, smarter way to build pipelines than any manual outreach
team.
Our Vision
To become the default growth engine for sponsorship acquisition in modern sport.
Our Team
Our Founder
Rich Cronin
Founder & CEO
With over 20 years of direct experience leading outreach and commercial strategy across management consulting and elite sport. He has personally run and scaled outreach in high-stakes environments where credibility, tone and trust determine whether conversations progress.
Advisors
Joe & Julie Foster
Advisors
Joe Foster co-founded Reebok in 1958, transforming a small Bolton shoemaking business into one of the world's most iconic sports brands. Julie Foster is Managing Director of J.W. Foster Heritage, preserving the legacy of the brand and mentoring the next generation of entrepreneurs. Together, they bring decades of experience building global brands from the ground up.
Charlotte Kenny
Advisor
Charlotte Kenny is a growth-focused CEO, board advisor and commercial operator with more than two decades’ experience across sport, technology and entertainment. Her career includes leadership roles at Arsenal Football Club, BLAST and EDF Group. She has led international teams and major commercial operations, delivering growth across sponsorship, media, digital innovation and market expansion. Charlotte brings deep expertise in building valuable senior-level commercial relationships.
Hugo Bennett
Advisor
Hugo Bennett is a commercial partnerships leader with extensive experience across sport, entertainment, gaming and brand marketing. Formerly Managing Partner at Ingenuity, he led its Brand Partnerships division and helped secure major sponsorship relationships, including a record partnership for the Rugby League World Cup. Now Head of Partnerships at GIANTX, Hugo brings deep expertise in sponsorship strategy, commercial growth and building high-value brand relationships.
Our Team
Our Founder
Rich Cronin
Founder & CEO
With over 20 years of direct experience leading outreach and commercial strategy across management consulting and elite sport. He has personally run and scaled outreach in high-stakes environments where credibility, tone and trust determine whether conversations progress.
Advisors
Joe & Julie Foster
Advisors
Joe Foster co-founded Reebok in 1958, transforming a small Bolton shoemaking business into one of the world's most iconic sports brands. Julie Foster is Managing Director of J.W. Foster Heritage, preserving the legacy of the brand and mentoring the next generation of entrepreneurs. Together, they bring decades of experience building global brands from the ground up.
Brooklyn Pickleball Team
