About
About Me
I currently serve as Chief Commercial Officer at Flywire (Nasdaq: FLYW)…
I currently serve as Chief Commercial Officer at Flywire (Nasdaq: FLYW)…
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7K followers
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Allison MacLeod reposted thisAllison MacLeod reposted thisI am ~60 days in at Flywire! I am thrilled with my decision to join this team and incredibly energized by all the growth opportunity in front of us. I am also actively recruiting to fill TWO full-time openings on the Product Marketing team. If you are the type of PMM who is solving for visibility, responsibility, and impact, then this could be the exact type of career acceleration opportunity you've been looking for. Flywire is quickly gaining share in large, growing markets, and our vertical model offers the autonomy and strategic leadership that great PMMs always want (and rarely find). Both job postings are below. Interested? Please apply directly! Know someone? Please share! PMM, Travel: https://lnkd.in/g9zEs3bJ PMM, Education: https://lnkd.in/ghB2A9BV
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Allison MacLeod shared thisOne of the best parts of my job is bringing our clients together and seeing the conversations that happen when everyone is in the same room. This October, we’re heading to Austin for #FlywireFusion. Over three days, we’ll talk about what is changing across higher education, payments and technology, share what is working and learn directly from the institutions who are leading the way. I’m looking forward to opening the event, sharing our vision for what comes next and, most importantly, spending time with so many of our US clients. If you haven’t registered yet, there is still time: fusion.flywire.com See you in Austin! #FlywireFusion2026 #HigherEd #Fintech
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Allison MacLeod shared thisThe experience of golfing just got a whole lot better! Exciting news with Flywire & Travelling The FairwaysAllison MacLeod shared thisWe are excited to announce that Travelling The Fairways—a premier golf tour operator across the UK and Ireland—has selected Flywire as its exclusive payments partner. By replacing a legacy general processor, Travelling the Fairways is delivering a true five-star checkout experience for international golfers. With Flywire, high-net-worth guests gain upfront price transparency in their local currency, while Travelling the Fairways lowers card processing fees and eliminates manual Excel reconciliation across its multi-entity operations. As experiential travel continues to scale globally, payment infrastructure must match the top-tier hospitality standards guests expect from the moment they book. Read the full announcement to see how Flywire elevates global travel payments: https://lnkd.in/gkKsTyqn #TravelTech #Fintech #LuxuryTravel #TravelByFlywire #GolfToursPremium Inbound Tour Operator Travelling the Fairways Selects Flywire as Exclusive Payments PartnerPremium Inbound Tour Operator Travelling the Fairways Selects Flywire as Exclusive Payments Partner
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Allison MacLeod shared thisAllison MacLeod shared thisWe are excited to announce the expansion of our partnership with Trustly, bringing "Pay by Bank" open banking capabilities to payers across the U.S. and Canada. Building on years of successful collaboration across Europe, this expansion enables payers to authorize high-value domestic and cross-border payments directly using their online bank credentials. By eliminating the need to manually enter routing or account numbers, we are removing payment friction, reducing payment failures, and eliminating unexpected wire fees. As Kate Moran, VP of Global Payments at Flywire, noted, our clients want modern, digital payment experiences that deliver speed, transparency, and accuracy. Bringing our proven European open banking infrastructure to North America delivers on that exact promise. Read the full press release to learn more: https://lnkd.in/gH3nGWsf #Fintech #OpenBanking #PayByBank #PaymentsFlywire Expands Trustly Partnership to Deliver Open Banking Payments Across the U.S. and CanadaFlywire Expands Trustly Partnership to Deliver Open Banking Payments Across the U.S. and Canada
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Allison MacLeod reposted thisAllison MacLeod reposted thisWe are thrilled to share that Flywire has been named to CNBC ’s World’s Top FinTech Companies of 2026 in the Payments category! 🏆 CNBC evaluated top fintech organizations globally, recognizing Flywire for our leadership in solving mission-critical, high-value payment complexity across education, healthcare, travel, and B2B. As our CEO Mike Massaro shared: "Solving complexity is a key competitive advantage for us. We go where others are unwilling or unable to go — and once we are embedded in the workflow, we become indispensable." A huge thank you to our incredible team of FlyMates, clients, and global partners who make recognitions like this possible! Check out the full list from CNBC: https://lnkd.in/e2M5gzjX #Flywire #Fintech #CNBCTopFintech #Payments #FintechNews
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Allison MacLeod shared thisTom Flanagan is building out our PMM team Flywire. For all you product marketers, this is a fantastic opportunity!Allison MacLeod shared thisWe're hiring a Boston-based PMM at Flywire ($FLYW) to help accelerate growth in our Education business. Product Marketing at Flywire is a strategic business function. We're looking for a revenue-oriented PMM who thinks as much about sales plays and pipeline metrics as messaging and positioning. We're also redefining how we scale PMM with AI at the core. The ideal candidate is an AI-first builder who will push us to innovate even faster. This high-visibility role in our flagship vertical can be an incredible career growth opportunity for the right person. If it sounds like a fit for a PMM in your network, please send them this link and encourage them to apply. 🙏
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Allison MacLeod shared thisLinkedIn network: know any amazing enterprise sales pros? We are hiring on our US education team! Roles open in Boston, Southeast. Come join an incredible team supporting the most innovative universities in US higher ed transforming the student financial experience. Check it out👇
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Allison MacLeod shared thisCongrats to our resident super 🌟 Mike Massaro! So well deserved! 👏Allison MacLeod shared thisWe’re excited to share that our CEO, Mike Massaro, has been named a 2026 Tech Power Player by Boston Globe Media! 👏 This recognition reflects the innovation, leadership, and impact he continues to drive at Flywire and across New England’s technology ecosystem. Learn more and see the full Tech Power Players list at Globe.com/tech50. #InsideFlywire #Leadership #BostonGlobe #GlobeTech50
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Allison MacLeod shared thisGo BenAI! No surprise to see this recognition! 🎉Allison MacLeod shared thisWe’re thrilled to share that Flywire’s own Ben Rubenstein, Senior Manager of Digital Marketing & AI, has been named to VentureFizz’s Top AI Marketers in Boston list! 🚀 As AI shifts from isolated tasks to production-ready workflows, Ben has pioneered Flywire's transition into sophisticated, agentic growth. By engineering custom automation agents tied to real-time ad data and building advanced Generative Experience Optimization (GEO) monitoring tools, he has kept our brand at the absolute forefront of modern search. Congrats, Ben, on this well-deserved recognition and for constantly pushing the boundaries of what's possible in fintech marketing! Check out the full list of honorees from VentureFizz here: https://lnkd.in/gur2bxby #Flywire #Fintech #AIMarketing #VentureFizz #TechInnovation #GenerativeAI #BostonTech
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Allison MacLeod liked thisAllison MacLeod liked thisToday is International Women in Cyber Day I'm #grateful to have worked alongside, learn from, and collaborate with so many sharp women; as friends, colleagues, partners, and customers. From #startup teams to the #Leaders and hands-on #practitioners working in the logs, managing systems, and solving real problems every day. Thanks to all the #builders and #defenders keeping industry moving forward. #InternationalWomenInCyberDay #WomenInTech #Cybersecurity Prospectorz SalesLair
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Allison MacLeod liked thisAllison MacLeod liked thisHappy International Women in Cyber day to all who celebrate! And this is one worth celebrating, as women are under-represented in cyber. Shout out to the women and women-led orgs whose brilliance, leadership, insights, and programming have helped me so much as relative newbie (~6-ish years) to this complex and every-changing industry. Lauren Taylor Catherine Kaiser Alice Collins Lisa Hayashi Ashley Ray Gianna Whitver Dani Woolf Jessica Sexton Women in CyberSecurity (WiCyS) Chicago Vision and Voice Crystal Hazen Emily Heath Megan Sawle Jamie Walker Sandra Carreon - Global MBA and so many more I'm forgetting. Let's keep defending! #womenincyber
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Allison MacLeod liked thisAllison MacLeod liked thisFor nearly 15 years, I sent Tim Cook a weekly report every Sunday night on the global App Store business. My team and I packed it with data, charts, and commentary on what was happening around the world. Most weeks: silence. Every so often, a probing question would come back about a specific metric or market. Or, better, a note congratulating us on a strong quarter. Those reports taught me a lot about discipline and accountability. No matter where I was in the world, I sent that report. Tim expected his leaders to know their businesses cold. Whenever I put anything in front of him, I needed to understand not just the numbers, but what was driving them and what we were doing about it. His expectations made me a much better leader. On my last day at Apple, Tim and I had a 10-minute 1:1 scheduled. We talked for 30. Reflecting on my 21 years at the company, he told me my greatest accomplishment wasn’t helping build a $1 trillion App Store ecosystem or helping scale the business to more than one billion customers. It was the team I had built and the leaders I had developed who were ready to step up after I left. That meant the world to me. We took this photo together right after that conversation. Today is Tim’s last day as CEO of Apple. Much has been written about what he and the company accomplished under his leadership. But perhaps his greatest legacy is the one he taught me to value: the people he developed, the culture he shaped, and the leaders ready to carry it forward. I’ll always be grateful I got to be a part of it.
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Allison MacLeod liked thisGood company to be in!Allison MacLeod liked thisWe are honored to be recognized as a 2026 Intelligent Applications 40 winner! 🎉 The #IA40 recognizes the 40 most important private companies in applied AI. Thanks to Madrona AWS Startups, Microsoft, Google for Startups, NYSE, Delta Air Lines, & McKinsey & Company for the recognition! More here: https://lnkd.in/gsdk7seP
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Allison MacLeod liked thisAllison MacLeod liked thisAs a follow up to my LinkedIn post asking for SKO ideas, I wanted to give back and share a couple of highlights that worked exceptionally well for our virtual Sales Kickoff last year. Our theme was Mission: Possible. It resonated with our global audience because, let's be honest, most of us feel like we're on a mission every day and everyone has seen one of the MI movies. The theme gave us a fun way to celebrate the important work our teams do while reinforcing that, together, we can accomplish things that might initially seem out of reach. Highlight #1 On Day 1, we posted a simple AI prompt and challenged attendees to create their own action movie poster using a headshot. The result? Hundreds of personalized posters featuring our sellers, engineers, leaders, and support teams as the heroes of their own action movie. (I've attached mine 😊.) The activity accomplished several things: · Drove engagement in a virtual setting · Gave everyone hands-on experience with AI in a low-pressure way · Created a sense of community across a global audience · Produced content that attendees genuinely wanted to share But the real magic came at the end of the event. We reused all of the employee-generated movie posters from around the world and created a slideshow to close out SKO. Seeing colleagues transformed into action heroes had everyone laughing, cheering, and searching for familiar faces. It was a simple idea, but it became one of the most memorable moments of the week. I also created a custom movie poster for every speaker and paired it with a walk-up song to introduce their session. We framed each one as an incoming "mission briefing," which ended up being a fun way to carry the theme throughout the event. Highlight #2 Our AI session. (Yes, of course we couldn't have an SKO and not talk about AI. 😄) Rather than talking about AI, we demonstrated it live. We showed attendees how prompting can support real sales motions using a simple framework: The key? Live prompting by actual reps and managers! And yes... I was nervous. The field watch their peers research accounts, prepare for meetings, and build account plans in real time. It removed much of the mystery around AI and helped people see how it could actually support their day-to-day work. For many attendees, it was one of those "aha" moments that shifted their thinking from "AI is interesting" to "I can actually use this tomorrow." These are just two of the highlights from our virtual SKO, but if anyone is interested, I'm happy to share more details. I hope some of these ideas spark inspiration for others who are currently planning their SKO and looking for ways to create a memorable experience. Let's SKO! 🚀
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Allison MacLeod reacted on thisAllison MacLeod reacted on thisQ2 2026 results are in! We signed over 200 new clients across 45 countries, demonstrating the strength and diversification of our business. When institutions and global businesses replace fragmented vendors and heavy manual processes, they choose Flywire to manage their most complex payment operations. Here’s how our key themes delivered this quarter: 🎓 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗩𝗲𝗻𝗱𝗼𝗿 𝗖𝗼𝗻𝘀𝗼𝗹𝗶𝗱𝗮𝘁𝗶𝗼𝗻: In a marquee win, The University of Liverpool selected our Student Financial Software (SFS) platform in the UK to consolidate billing, payment plans, and refunds into a single portal with real-time Unit4 ERP integration. In the US, we signed 3 new SFS deals at double the ARR value of Q2 2025. 🌏 𝗚𝗲𝗼𝗴𝗿𝗮𝗽𝗵𝗶𝗰 𝗗𝗶𝘃𝗲𝗿𝘀𝗶𝗳𝗶𝗰𝗮𝘁𝗶𝗼𝗻: Education revenue outside our "Big 4" markets grew over 30% YoY. We expanded our footprint in Europe and Asia - including prestigious university wins in South Korea and Japan - while winning key accounts like Sheridan College in Canada and Bond University in Australia. 💻 𝗦𝗼𝗳𝘁𝘄𝗮𝗿𝗲-𝗟𝗲𝗱 𝗠𝗼𝗻𝗲𝘁𝗶𝘇𝗮𝘁𝗶𝗼𝗻: Major hotel management groups—including Peregrine Hospitality, Avion Hospitality, and Marcus Hotels—signed on to attach payments to our software. In B2B, new clients like a digital asset manager, a wealth management firm, and an international insurer adopted our Invoiced software and payment rails together from day one. And in healthcare, many large health systems are managing the full patient financial experience through Flywire, as well as payment processing. Our client momentum comes down to a clear formula: replacing vendor complexity with a single platform that delivers measurable ROI. Thank you to our incredible team of FlyMates and partners for another quarter of executing for our clients. 💪 https://lnkd.in/djYRhW4mFlywire Reports Second Quarter 2026 Financial Results | FlywireFlywire Reports Second Quarter 2026 Financial Results | Flywire
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Allison MacLeod reacted on thisAllison MacLeod reacted on thisWelcome to NYU International students from around the globe.
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Allison MacLeod reacted on this135 events and growing! Boston AI Week has something for everyone - from AI in Oncology to a Robotic Block Party 🤖 If you are not sure where to start, check out the filter and search capabilities to find the events of greatest value for you. Some easy places to start: The Boston AI Week Opening Party at Island Creek Oyster Raw Bar in the Seaport on 9/25 The Boston Generative AI Meetup at Laugh Boston on 9/28 The Boston AI Summit Flagship Conference at Foundation Medicine in the Seaport on 10/1 Whether you are in legal, manufacturing, healthcare, education, software development, customer success, sales, marketing, architecture, government, cybersecurity - just about anything and everything - there is something to learn and great people to meet during Boston AI Week! https://lnkd.in/ghzwEJ8a #AIinMedicine #AIinLegal #AIpolicy #AIInnovation #Founders #VentureCapital Judah PhillipsBoston AI Week 2026 Schedule — 120+ AI Events in MassachusettsBoston AI Week 2026 Schedule — 120+ AI Events in Massachusetts
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Allison MacLeod reacted on thisA new year @Harvard! #HarvardProudAllison MacLeod reacted on thisIt's the start of a new chapter, for both students and parents 🥹
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Eloqua Master Certified
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