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- 💡 Ireland’s Own "PayPal Mafia": The Rise of the Digicel Mafia
💡 Ireland’s Own "PayPal Mafia": The Rise of the Digicel Mafia
Deep Dive #4
Stephen Mullan
September 24, 2024
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In the world of tech and entrepreneurship, the story of the PayPal Mafia is legendary. This group of former PayPal employees used their experiences at the online payment giant to launch some of Silicon Valley's most successful companies, including Tesla, LinkedIn, and YouTube.
But while the PayPal Mafia might be the most famous alumni network in tech, Ireland has its version in the form of the Digicel Mafia—a network of former Digicel executives who have gone on to achieve remarkable success in industries across the globe.
Like their PayPal counterparts, these Digicel alumni have leveraged their time at the Caribbean telecom giant to lead ventures in fintech, AI, telecom, and e-commerce. This Irish-born telecom company has produced a cadre of entrepreneurs and business leaders who are now shaping industries far beyond the Caribbean and Pacific islands, where they honed their skills.
👑 PayPal Mafia: Silicon Valley’s Elite
A visualisation of the Paypal mafias achievements
The PayPal Mafia refers to a group of former PayPal employees and founders who, after PayPal was acquired by eBay in 2002, became some of the most influential figures in the tech world. The name was cemented by a 2007 Fortune magazine cover showing them dressed in black suits and sunglasses like a mafia family. Key members of the group include:
Elon Musk, founder of Tesla and SpaceX.
Peter Thiel, co-founder of Palantir and early Facebook investor.
Reid Hoffman, founder of LinkedIn.
Steve Chen, Chad Hurley, and Jawed Karim, co-founders of YouTube.
These individuals didn’t just achieve personal success—they supported each other, invested in each other’s ventures, and became a dominant force in Silicon Valley, creating a web of innovation and investment that still influences today's tech industry.
🌐 Digicel: From Jamaican Telecom to Global Giant
Digicel, founded by billionaire Irish entrepreneur Denis O’Brien in 2001, revolutionised the telecom landscape in Jamaica and quickly expanded across the Caribbean, Central America, and the Pacific. O’Brien’s vision was simple: enter underserved markets where mobile communication was expensive and inaccessible and offer affordable, reliable services. (Company Profile)
Digicel Founder Denis O’Brien
Digicel’s growth was nothing short of remarkable. It became a telecom powerhouse, operating in over 30 countries, serving millions of customers, and providing mobile services where they were desperately needed. O’Brien’s focus on customer satisfaction, competitive pricing, and community engagement helped the company grow rapidly, especially in markets with low mobile penetration.
As Digicel expanded, it became a breeding ground for talented professionals, many of whom would lead major businesses and ventures worldwide. These alumni, much like the PayPal Mafia, have created their own legacy across various industries.
Meet the Members of the Digicel Mafia
Just as the PayPal Mafia reshaped Silicon Valley, the Digicel Mafia has left its mark on global industries. Here’s a closer look at some of its most prominent members, their contributions at Digicel, and their achievements after leaving the company.
Conor Looney – CEO at EXO Edge and LDM Global 🇺🇸
What Conor did at Digicel: Conor spent over six years at Digicel in senior leadership positions, including as Regional CEO for the Caribbean and Central America. His roles spanned various markets in the Caribbean, where he was responsible for driving Digicel’s market growth and overseeing operations across 18 countries. |  |
Post-Digicel Achievements:
CEO at EXO Edge: Conor now leads EXO Edge, a business process outsourcing firm focused on real estate, using his telecom experience to drive efficiency in new industries.
CEO at LDM Global: He also heads LDM Global, specializing in eDiscovery and AI analytics services, proving his adaptability across sectors.
Gary Cobain – CEO & Founder of PokitPal 🇦🇺
What Gary did at Digicel: Gary served as CEO of Digicel Business Solutions, leading a team across six countries in the South Pacific. He focused on transforming Digicel into the number one ICT provider in the region, expanding its business solutions arm. Check out Gary's Founder Focus profile here. |  |
Post-Digicel Achievements:
CEO & Founder at PokitPal: Gary founded PokitPal, a fintech company that enhances customer engagement through rewards programs, marking his successful transition from telecom to fintech.
Business Mentor: Gary also mentors fintech startups at Stone & Chalk in Australia, helping guide the next generation of entrepreneurs.
Des Wynne – CEO at Lazer Telecom 🇵🇹
What Des did at Digicel: Des held various senior sales and business development roles at Digicel, including Director of Business Sales for the Dutch Caribbean. His work in Aruba and Curacao showcased his ability to drive growth in both mobile and ICT sectors. |  |
Post-Digicel Achievements:
CEO at Lazer Telecom: Des now leads Lazer Telecom in Portugal, where he oversees all operations, utilizing his telecom background to grow Lazer’s footprint in the region.
Group Sales Director at Simtech Aviation: He previously worked in aviation, further demonstrating the diverse paths Digicel alumni have taken.
Sarah Martin – CEO at Pulsate 🇮🇪
What Sarah Did at Digicel: Sarah worked as Digicel's Commercial and Marketing Director in the Eastern Caribbean. Her marketing expertise and focus on fiber acquisitions contributed significantly to Digicel’s regional expansion. |  |
Post-Digicel Achievements:
CEO at Pulsate: Sarah now leads Pulsate, a mobile-first growth platform for financial institutions, blending her telecom experience with cutting-edge technology solutions.
Founder of Mamabud: She also founded Mamabud, a platform that facilitates market access to China, reflecting her entrepreneurial drive.
Michael Murphy – CEO at Luas Partners 🇮🇪
What Michael Did at Digicel: Michael was the CEO of Digicel Group from 2015 to 2017, managing operations in Singapore. His leadership focused on expanding Digicel’s reach in the competitive Asia-Pacific region. |  |
Post-Digicel Achievements:
CEO at Luas Partners: Michael is now the CEO of Luas Partners, a business consultancy in Dublin.
CEO at BidX1: He previously led BidX1, a digital real estate platform, applying his expertise in scaling businesses to a new industry.
Maurice McCarthy – Managing Director of Customer Success at Optus 🇦🇺
What Maurice Did at Digicel: Maurice held multiple leadership roles at Digicel, including CEO of Digicel Papua New Guinea and Regional CEO of Digicel Pacific. His tenure was marked by operational leadership and driving growth in emerging markets like Fiji and PNG. |  |
Post-Digicel Achievements:
Managing Director at Optus: Maurice leads customer success operations at Optus, one of Australia’s largest telecom companies. His experience in growing telecom services in developing regions has positioned him as a key player in the Australian market.
VP of Retail at Optus: Before his current role, Maurice also led retail and channel sales at Optus.
Derek Burke – CEO & Co-Founder of UMEGO 🇸🇬
What Derek Did at Digicel: Derek served as Chief Operating Officer at Digicel from 2015 to 2018, playing a vital role in leading the company’s e-commerce and digital ventures across the Caribbean and Asia-Pacific. |  |
Post-Digicel Achievements:
CEO & Co-Founder at UMEGO: Derek co-founded UMEGO, a social networking platform that merges digital and real-life interactions, showcasing his innovative approach to connecting people.
Chief Commercial Officer at Amilo: Derek is also a co-founder of Amilo, a logistics company solving e-commerce challenges in Southeast Asia.
John Clancy – Founder & CEO of Galvia 🇮🇪
What John Did at Digicel: John held senior roles, including CEO of Digicel Vanuatu, where he managed telecom operations in some of the most challenging markets in the South Pacific. |  |
Post-Digicel Achievements:
Founder & CEO of Galvia: John now leads Galvia, an AI platform that helps companies make data-driven decisions, applying his telecom leadership skills to the tech industry.
Government Advisor: John also advises the Irish government on AI and digital technologies.
James Gormley – Co-Founder & COO of Campsited 🇮🇪
What James Did at Digicel: James was Group Technical Project Manager for Digicel, overseeing product delivery across multiple markets, including Jamaica. |  |
Post-Digicel Achievements:
Co-Founder & COO at Campsited: James co-founded Campsited, an online platform connecting campers with campsites globally, applying his technical project management expertise to a new industry.
Just like the PayPal Mafia, the Digicel Mafia is a testament to how one company can shape the future of industries across the globe. From telecom to fintech, AI, and e-commerce, Digicel’s alumni have gone on to create a lasting impact in their fields.
The Digicel Mafia highlights the talent that grew within the company and the invaluable experience gained from working in high-growth, emerging markets. These entrepreneurs and leaders are a testament to the power of Irish innovation and global ambition.
If we missed anyone who should be on this list, reply and let us know. 🤝
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