Women’s History Month Spotlight with Alyssa May
BY Team Practifi
In celebration of Women’s History Month, we are proud to bring back our spotlight series for a second year, highlighting the contributions and journeys of women shaping the wealth management and finance industry. This year, we are honored to feature five remarkable women leaders who have forged their own paths in wealth management technology, driving innovation, advocating for inclusivity and making a lasting impact in this evolving space. Through their stories, we celebrate their achievements, highlight their expertise and share valuable insights from their unique experiences.
Meet Alyssa May, Director of Learning at Practifi. Alyssa’s journey from media to fintech and ultimately to leading education initiatives for financial professionals, reflects the power of curiosity, adaptability and a passion for learning. Throughout her career, she has been a champion for diversity, inclusion and professional development, ensuring that financial professionals are empowered to grow with the tools they use.
In this interview, Alyssa shares her career journey, insights on the evolving fintech landscape and advice for women striving to make an impact in the industry.
Curiosity, Questions and the Unexpected Road to Fintech
Alyssa’s career path wasn’t a direct route into fintech. She started in marketing and media, working in advertising before transitioning into financial technology. But instead of simply following a traditional career ladder, Alyssa embraced her curiosity, continuously asking questions, digging deeper into systems and ultimately discovering a passion for education and training.
Q: Can you share a bit about your background and journey into the wealth management industry?
A: I actually started in marketing and advertising. I worked for an advertising agency doing media buying, but I’ve always been the type of person who wants to understand how things work — not just how to use a tool but truly learning the mechanics behind it. That curiosity led me to ask a lot of questions about the systems we used, which ultimately pushed me into operations and technology.
From there, I transitioned into financial technology at Morningstar, where I worked with supporting teams in using their financial data software. I quickly realized that many advisors weren’t fully utilizing the tools available to them, and that’s what led me into training and education. At Practifi, that same passion drives me. Wealth management technology is constantly evolving, and firms need continuous education and training to keep up. It’s incredibly fulfilling to help financial professionals gain confidence in the tools they use.
Q: What inspired you to pursue a career in this field? Was there a defining moment?
A: It wasn’t a single moment, but more of a series of realizations. Every step of the way, I found myself wanting to help people learn and navigate technology.
When I started at Practifi, I was working closely with clients, and I quickly noticed a reoccurring pattern: advisors were struggling with the same things over and over again. I realized that we needed a structured education program to help them onboard and grow with the product, rather than just answering individual questions every time they came up. That was a turning point for me. I saw an opportunity to create something that would solve a bigger problem, not just a one-time frustration. That’s how I started Practifi’s Learning Team.
I became its first official member and later expanded the team to create internal and external training programs like PractifiU, and resources that help advisors get the most out of our platform.
Hardwork vs. Happenstance: Owning Your Path
It’s a common narrative that many professionals, especially women, say they “fell into” their careers rather than actively choosing them. But Alyssa challenges that mindset. She believes that hard work, determination and adaptability play a bigger role in career success than luck ever could. Alyssa shares her perspective on why owning your journey is so important and how embracing your skills can lead to long-term success.
Q: Many women say they ‘fell into’ wealth management rather than seeking it out. Do you think this is true?
A: I think it’s a falsehood. I think women are often told that their success is a result of luck or happenstance, but the truth is, we work incredibly hard to get where we are.
Yes, sometimes an opportunity arises at the right time, but it’s about what you do with that opportunity. Women are so quick to downplay their achievements, saying, “I just got lucky,” when in reality, they’ve delivered great results, worked hard and brought immense value. We need to own that.
The Power of Representation
The financial and technology industries have historically lacked diversity, particularly in leadership roles. Leadership isn’t just about having a title. You have to have a voice, a seat at the table and the ability to make meaningful changes. Alyssa believes that companies thrive when leadership reflects the diversity of the teams they manage.
Q: How has the industry evolved in terms of diversity and inclusion?
A: It’s getting better, but there’s still a long way to go. While we see more diversity in sales, marketing and learning teams at tech firms, when it comes to engineering, leadership and executive roles, the gender imbalance is still noticeable.
One positive shift is that companies are talking more about diversity and inclusion, which is a step in the right direction. But talking about it and actively making changes are two different things. It’s not just about hiring more women, it’s about creating spaces where many diverse voices are heard, valued and respected.
Q: What are your thoughts on the current level of representation of women in leadership roles within the industry?
A: There’s still a significant gap, especially in technical and leadership positions. One of the biggest challenges is that companies often promote from within familiar circles that already lack diversity. If leadership teams are made up of individuals who followed a traditional route into fintech, they may overlook candidates who took non-traditional paths or bring different perspectives to the table. If you look around the room and everyone looks the same, you’re missing out on new ideas. Companies need to actively make space for different perspectives.
Q: What role do you believe women play in shaping the future of wealth management?
A: We play a huge role whether the industry acknowledges it or not. Women bring unique perspectives that challenge outdated norms and drive innovation. We think about the user experience differently; we push for more collaborative problem-solving and we bring fresh ideas that wouldn’t exist in a room that looks the same as it did 20 years ago. We also advocate for inclusivity in financial technology, ensuring that solutions are designed for a broader audience rather than just one traditional user base.
Q: How can companies actively promote and support the advancement of women into leadership positions?
A: It starts with access to mentorship, sponsorship and intentional hiring practices. Women need real opportunities to step into leadership and not just more responsibilities with no title change. Companies should be looking at:
- Internal leadership development programs
- Sponsorship from executives who champion emerging leaders
- Flexible work environments that allow more women to pursue leadership
And most importantly, companies need to listen to their employees and ensure that leadership pathways are open to everyone and not just those who fit a pre-existing mold.
Balancing Career Growth and Motherhood
Becoming a parent is one of the biggest life transitions anyone can experience. For working professionals, it brings new priorities, challenges and responsibilities but also a different kind of motivation. For Alyssa, navigating career growth while raising a family has been a journey of finding what balance really means. She believes that companies play a huge role in supporting working parents, and that the right culture makes all the difference.
Q: How do you balance career growth and motherhood?
A: I know this isn’t a popular answer, but balance is a myth. Every day is a juggling act, and sometimes you’ll feel like you’re dropping all the balls.
I joined Practifi before I had kids, and now I have two under the age of four. That transition was huge, and I won’t pretend it’s easy. Your brain splits into two priorities, and some days, it feels like you’re failing at both. But I try to remind myself: showing up and doing my best is enough.
I’m incredibly fortunate that Practifi has a supportive culture for parents. When I was the first U.S. employee to go on family leave, we had to build that policy from scratch. The company made sure it was meaningful, aligning with the support given to employees in other countries. That made all the difference for me, and it’s something I wish more companies prioritized.
Q: What advice would you give to women entering the wealth management industry?
A: Apply for the job even if you don’t check every box. Women tend to hold themselves back, thinking they need to meet 100% of the qualifications before applying. Those requirements are a starting place for a perfect candidate. Take the leap.
Only you can advocate for yourself. Call out your wins, take credit for your work and don’t be afraid to ask for that promotion, raise or opportunity. And where you can, find a mentor and a support system. Navigating a male-dominated industry can be challenging, but having good people in your corner makes all the difference.
Progress Starts with Us
Success doesn’t follow a set path. Success is built through curiosity, perseverance, and the willingness to step into new opportunities, even when they feel uncertain. Whether you start in a completely different industry, take an unexpected career turn or carve out a new role entirely, what matters is that you keep moving forward, keep learning and trust in your ability to grow.
Alyssa’s journey is a reminder that you don’t need to have all the answers to take the next step. The most impactful careers are often shaped by those who ask questions, resist the status quo and create solutions where none existed before. As we celebrate Women’s History Month, her story reminds us that progress happens when women push forward, challenge norms and make space for others.
Thank you, Alyssa, for sharing your insights and experience! Stay tuned for more Women’s History Month Spotlights as we continue highlighting trailblazing women in the industry.
