Give to Gain: Career Wisdom from the Women of Flywire

In honor of Women’s History Month, we asked the incredible Women of Flywire a single guiding question: "If you could gift one piece of career advice to every woman at Flywire, what would it be?"

The responses we received embody the theme of "Give to Gain." By sharing their hard-earned lessons and "borrowed wisdom," our FlyMates are helping our entire community rise. From the power of authenticity to the importance of taking risks, here is the collective wisdom of our team.

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Embrace Your Authentic Self

Many FlyMates emphasized that staying true to who you are is a fundamental strength at Flywire.

  • Samantha Mackowitz (Social Media and Internal Comms Manager, Remote US): "If I could gift one thing, it would be the confidence to stay true to your authentic self. We often feel we have to change to gain ground in our careers, but at Flywire, we know that authenticity is where our real strength lies."
  • Dani Bennett (Senior Manager, Content Marketing, UK): "Be your authentic self. It's all too easy to create a persona for work, but it is almost never sustainable. Being as authentic as you can be within your profession helps create connection and build trust."
  • Ilona Mojila (Senior Program Manager, People Operations, Valencia, ES): "You are enough. You don’t need to become someone else to succeed. Everything you already carry—your strength, your doubts, your knowledge, your emotions—is part of what makes you powerful."
  • Nicole James (Chief People Officer, Remote, US): “Be unapologetically you! Everyone's path is different and everyone's definition of success is measured differently. Your career and the intersection of it with all that you do in life is measured on your terms only.”

Take Ownership and Be Bold

Growth often comes from stepping outside of your comfort zone and being bold in your choices.

  • Sharon Butler (Co-President, Global Education, Remote US): "Take ownership before you feel fully ready. Some of the biggest opportunities in my career came when I stepped into something that felt a little bigger than my experience at the time. If you wait until you feel 100 percent prepared, the opportunity will often pass you by."
  • Anu Gorur (Senior People Success Manager, Boston): "Be bold in your career and life choices - Don't be afraid to take the road less travelled."
  • Truc Huynh (Payment Experience Specialist, Pay Any School, Singapore): "Don’t wait for perfect confidence to take the next step - you’ll grow into it as you go. And as you do, remember to lift as you climb."

Stay Curious and Invest in Yourself

The best way to "Gain" is to never stop learning and asking questions.

  • Rebecca Heredia (Director, Global People Partner, Sydney): "Invest in your skills, personally and professionally, every year. In a world where people and places can be temporary, skills are permanent."
  • Divija Kambhampati (Sr. Business Intelligence Analyst, Remote US): "Be curious. Ask questions—there’s no such thing as a wrong one."
  • Amy King (Director, Brand & Content, Remote US): "Stay humble, curious, and in a constant state of learning. The deeper your skill set and network, the more doors you'll see open."

Build Confidence and Own Your Value

Recognizing your own worth and expertise is key to navigating any career path.

  • Ebony McNeill (Implementation Consultant II, Remote, US): "Never question whether you belong. You do. Your voice, your ideas, and your work matter."
  • Sarah Christopher (Sr. Manager, Events, London, UK): "Channel your inner self confidence, you're the expert in your field and the specialist in what you do... speak up & have confidence in your abilities."
  • Catherine Eklund (SVP Global Partnerships & EDU Canada, Remote US): "Own your value: It is not defined by others. Your perspective, voice and presence matter - that is why you are in the room!"
  • Allison MacLeod (Chief Commercial Officer, Boston): "Believe in yourself. There will always be people who underestimate what you’re capable of. Don’t let that become your inner voice."

Practical Tips for Long-Term Success

  • Kate Simson (Chief of Staff, Remote, US): "The reminder to laugh at yourself is especially valuable. It keeps things in perspective and makes life so much lighter."
  • Naissa Kummer (Marketing, Australia): "Listening is one of the most valuable skills you can build in your career. When you take the time to truly understand the people around you, you build stronger rapport and trust."
  • Amelia Patterson (Client Success Manager, Remote, US): "They don't know unless you tell them! Keep a written record of your wins and update it quarterly... Make it easy for them to promote you."
  • Deepika Sharma (Agent Partnership Specialist Lead, India): "Cherish your passion, trust your journey, embrace challenges, and seek support—you are capable of far more than you imagine."
  • Talena Lange (US Director of Relationship Management, Boston): "Never underestimate the quiet strength of a positive mindset. Talent matters, but resilience, optimism, and belief in yourself are what carry you through."
  • Diana Lulgjuraj (Director of Procurement, Remote, US): "Don't compare yourself to others and compete. Instead, plan and build your own path towards your goals."
  • Sarah King (VP of Global Marketing, Boston): "If you build relationships first, the results will follow. When you invest in relationships over time, trust becomes your greatest efficiency tool."
  • Charmaine Daniels (Sr. Manager - Implementation Consulting, Remote, US): "Focus on your circle of influence, not your circle of concern! You make the biggest impact by focusing on the things you do have influence over."

Thank you to all our FlyMates who shared their wisdom. We are proud of the supportive, authentic community you continue to build every day.

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