At Flywire, we are continually focused on leveraging new technologies for smarter decision-making to empower Flymates across the globe and support our customers with top of the line solutions. If you caught our recent Flywire AI fireside chat, you caught a glimpse of our teams’ dedication to innovation first hand and Flywire’s new futuristic support beams—and they talk back. The panel, hosted by Philip Andersson, senior director of the learning & growth team, was made up of five Flymates from across the company who presented how the use of different AI tools are making their jobs and our clients' lives easier. Check out what they had to share.
Meet Your New Coworkers: Flywire’s AI Assistants
Chad Lieberman, AKA “ChadGPT”, data scientist on the data science team, introduced a new set of tools that have been six years in the making and are already changing the way we work: Flywire AI Assistants. Developed in collaboration with teams across the organization, Flywire AI Assistants are a suite of 14 internal chatbots designed to give FlyMates quick answers to key pieces of information. Each assistant is purpose-built and draws from internal sources including The Wire (Flywire’s Intranet), Confluence, Google Drive, and Zendesk—ensuring that responses are accurate, up-to-date, and relevant.
Suggested User: Any and every Flymate!
Key Capabilities:
- Delivers fast access to internal knowledge
- Helps Flymates work more efficiently, find information, learn new tools, explore and analyze their own data
Benefits & Applications:
- Searches for pre-screened documents to find answers to questions ie: “How do I create a new account”? or, “What is CashMatch AI?”
- Pulls live data from external integrations
- Aware of Flywire context - nomenclature, background, and motivation are provided
- Available globally to all Flymates 24/7
- Assistants are ready to use from day one and do not require additional uploads of documents
- Some assistants are accessible through Flywire's internal communication platform
Less Wait, More Wow: AI-Powered Support Agents
Victoria Stephens, senior director of the client and payment experience (CPE) team, shared three AI initiatives her team has been using to augment support and reduce manual work while improving the experience for our customers. They include: a chatbot configured to support payers and clients with payment-related inquiries within Flywire products, a voice bot configured to support the customer support phone line by gathering a caller’s intent to quickly answer their inquiries, and an intent detection tool used to pick up the intent of emails and provide autoresponses and autoresolutions. For the CPE team, the use of these tools isn’t just about efficiency—it’s about creating space for deeper, more meaningful customer connections. By using AI to handle routine questions, they can spend more time on nuanced support, proactive outreach, and strengthening relationships.
Suggested User: Clients and payers around the world
Key Capabilities:
- AI-powered chatbot integrated with payments data
- Voicebot for real-time support over the phone
- Intent detection for email inquiries to automate responses and resolutions
Benefits & Applications:
- Real-time payment updates: Enter a payment ID and get your payment status
- Multilingual support: Chat bot available in Spanish, Chinese, and Vietnamese
- Self-service tools that reduce wait times and lower operational costs
- Around-the-clock availability, ensuring customers can get help any time, from anywhere
- Personalized support at scale, freeing the CPE team to focus on high-value, complex interactions
From Questions to Confidence: AI-Powered IR Analyst
Masha Kahn, vice president of investor relations, put a spotlight on how AI is helping her team stay sharp, informed Flywire competitors, and always one step ahead when engaging with investors. Masha uses AI to predict likely investor questions ahead of earnings calls and to generate thoughtful, data-backed responses by pulling from strategy docs, business updates, financial metrics, and past commentary meaning less scrambling across teams and more time focusing on strategy and storytelling. Masha also shared how AI is being used to monitor peer and competitor discussions, forecast their disclosures and performance metrics, and even perform sentiment analysis on analyst commentary. These insights help sharpen communications when investors and help anticipate shifts within an investor’s perception in real time.
Suggested User: Investor relations, executive leadership, and corporate communications teams
Key Capabilities:
- Predicts investor questions using transcripts, news flow, and past commentary
- Pulls data and insights instantly using the “Ask Gemini” chat integration
- Tracks competitor discussions and forecasts peer metrics
- Performs real-time sentiment analysis to fine-tune messaging
Benefits & Applications:
- Faster response prep for investor inquiries—no more last-minute document scrambles
- Consistent, accurate messaging backed by historical data
- Proactive script development informed by sentiment trends
- Greater agility in Q&A sessions and market-facing communication
Clicks, Conversions, and Campaigns: AI-Powered Digital Marketing Associate
Ben Rubenstein, senior manager of digital marketing on the corporate marketing team, gave us a behind-the-scenes look at how he uses multiple tools with AI functions to reach the right people, with the right message, at the right time.
Starting with audience targeting, Ben uses Semrush for keyword optimization and 6sense to analyze company activity across to the web to gain visibility into where our audience is online. Next, to create the most effective ads for our audience, Ben uses Google’s AI chatbot Gemini to build out different campaign variations and Google Ads to identify which ads would be most responsive. And finally, for website optimization, Ben employs a digital experience platform called Optimizely to generate suggested messaging for the site and uses machine learning to collect website performance results. Ben’s conclusion? AI makes more experiments, faster insights, and a lot more leads possible.
Suggested User: Digital marketers and client-facing teams focused on lead generation and campaign performance
Key Capabilities:
- Keyword optimization using real-time site and search data
- AI-generated ad copy for faster campaign launches
- Dynamic ad testing and automated bidding strategies
Benefits & Applications:
- Reduced ad copy workload
- Doubled web testing experiments, leading to more optimized landing pages and higher conversion potential
- Accelerated time-to-launch, getting campaigns in front of the right people faster
Smarter Selling, Stronger Results: AI-Powered Sales Training & Effectiveness Associate
Brette Chmura, revenue operations manager on the marketing team, gave us a look inside Gong, an AI-based revenue intelligence platform that’s transforming the way sales and marketing teams sell. Gong records and analyzes external calls and emails with clients and provides actionable insights allowing FlyMates to be fully present in client conversations without missing a beat. With Gong, teams can automatically take notes, summarize meetings, identify risks, generate follow-ups, and track deal progress. Gong’s insight also feeds back into training and coaching, enabling teams to continuously build stronger relationships, shorten onboarding, and drive smarter strategies—deal by deal.
Suggested User: Sales, Marketing, and Client-Facing Teams
Key Capabilities:
- AI-powered notetaking on calls and emails
- Real-time syncing with Salesforce to provide detailed reporting on client accounts and the health of the sales pipeline
- Account and deal summaries with conversation insights
- Automated follow-ups and task tracking
Benefits & Applications:
- Analyzes sales calls and emails to gather insights on customer needs, objections, and competitor mentions
- Tracks real-time deal progress
- Reveals high performing messaging and campaigns based on buyer interactions for better marketing alignment
- Boosts win rates by highlighting top-performer behaviors
- Accelerates onboarding with recorded examples
- Allows FlyMates to focus on strategy, not just follow-ups
Advice from the Experts: Getting Started with AI
To close out the AI Panel, host Philip Andersson asked the presenters to answer a practical and timely question:
“What’s one piece of advice you’d give others about adopting AI?”
Each presenter brought a unique perspective to the table, shaped by how they use AI personally and professionally. Here’s what they had to say:
Chad Lieberman – Data Science
“Whenever you’re using these AI products, the AI won’t magically know what you’re talking about or what the context is of the problem you’re trying to solve, so it may take a bit of back and forth. Don’t just ask one question and give up if the answer isn’t right. Continue the conversation, add more information, and you’ll get back something truly helpful.”
Victoria Stephens – Client & Payer Experience
“My advice would be to start small—try it on something fun and personal, like creating a recipe or planning a trip. Once you see how practical and helpful it can be, it becomes easier to apply it to work. Stay curious, experiment, and as you learn to ask better questions, AI becomes a natural part of your workflow.”
Masha Kahn – Investor Relations
“If you ever want to know anything about Flywire’s business, come to me—or click the Gemini button. It will tell you everything we’ve ever said publicly. Whether you want to learn about healthcare, acquisitions, B2B, or travel—it’s all there, ready to explore.”
Ben Rubenstein – Corporate Marketing
“Feedback is everything. Don’t expect the perfect result the first time. In marketing, there’s always a promise of the ‘easy button,’ but AI needs time and data to learn what you actually want. Giving it the right context and high-quality data—while respecting privacy—pays off in the long run.
Brette Chmura – Revenue Operations
“AI gives you back what you put into it. With tools like Gong, the more context and data we provide—on deals, accounts, outcomes—the more useful and refined the insights become. It’s a loop: input leads to better output, and that helps us make smarter decisions going forward.”
Whether you’re new to AI or looking to deepen your use, the consistent message from the panel was clear: start small, be patient, provide context, and stay curious. The more you engage with the tools, the more powerful they become. Stay tuned for more innovation highlights as we continue building the future of fintech together.