Rosa Finelli
Rosa Finelli is an accomplished learning and development executive with over 23 years of experience building her career in the EdTech industry, specializing in leadership development, career management, and organizational growth. As Executive Director of Learning and Development at Kaplan North America, she leads strategic, competency-based learning programs that support leaders and employees across multiple business units. Her work focuses on designing and implementing onboarding initiatives, functional training, diversity and inclusion strategies, business process improvements, and ongoing employee development programs that strengthen both individual performance and organizational success.
Rosa’s professional journey began in drug and alcohol abuse counseling shortly after college before she transitioned into the call center sales environment, where she discovered her passion for coaching, development, and helping others succeed. That path eventually led her to Kaplan more than 23 years ago, where she started in admissions counseling, working directly with students to help them achieve their educational goals. From there, she moved into training and development, where she has spent the majority of her career, also gaining valuable experience in quality assurance and call center operations. Today, she leads a virtual learning and development team, partnering with internal business leaders to identify training needs, drive strategic initiatives, and build programs that create measurable impact. Her current focus includes AI implementation, helping employees adopt new technologies while continuing to prioritize leadership and employee development across the organization.
As the first person in her family to pursue a college education, Rosa’s journey is deeply rooted in resilience, ambition, and service. Raised by Italian immigrant parents who came to America in pursuit of opportunity, she learned the value of hard work early, helping her father with proposals and invoices as young as 13 because English was not always their strongest language. Choosing to step outside of her family’s business and build her own path in the corporate world became a defining part of her story. Climbing the corporate ladder at a young age and growing into a leadership role where she can influence, mentor, and develop others has been especially meaningful to her. Today, one of her greatest passions is mentoring emerging leaders and helping the next generation of professionals build confidence, capability, and purpose in their own careers.
• Certification in Leading Innovative Change from UC Berkeley
• Certification in Diversity and Inclusion from University of South Florida
• Graduate Certificate in Instructional Design for Organizations, Educational/Instructional Media Design
• University of Florida - BA, Criminology
• Purdue Global - MS in Management, Human Resources
• Spirit of Kaplan Award
• Kaplan Way Award
• ATD BEST Award (multiple times with team)
• Member of Association of Talent Development (ATD) - South Florida chapter
• Member of Association of Talent Development (ATD) - National chapter
• Mission work with Mission of Grace orphanage in Haiti - traveled to Haiti on numerous occasions to bring supplies and provide life skills mentoring to teenage and younger children
• Mission of Grace - Haiti
What do you attribute your success to?
Being the first person in my family to pursue a college education has been one of my most notable achievements. I'm the only child in my family who went to college, and stepping outside of my family's business to go after my own dreams of working in the corporate space was huge for me. My parents are Italian immigrants who came to America chasing the American dream, and their English wasn't always the best, so I started helping my dad with proposals and invoices when I was just 13 years old. He worked in interior design and new home construction, and my brothers and mom all worked for him, but I wanted something different. I wanted to pursue my own path. Climbing up the corporate ladder at a very young age and being able to position myself in an organization to help lead and influence others has been incredibly meaningful. Now, taking those experiences I've had and being able to mentor some of our younger leaders in the organization is one of my favorite things. I wouldn't have had it any other way, even though they put me to work at 13. That experience shaped who I am today.
What’s the best career advice you’ve ever received?
I had an incredible leader who just retired from Kaplan, and thankfully I still stay connected with her outside of work. She was a chief executive in our organization and an attorney by trade, but no matter what her title was, she led by the heart. You could tell that she truly cared about the people she was leading. She was someone who would say, 'Hey, if you don't agree, push back. Give me your thoughts. I want you to have a voice.' That's actually how our relationship started. She was asking me about 10 questions at once, and I said, 'Okay, I need a moment to process everything that you just said. I'm a reflective listener, a reflective learner.' She really appreciated the fact that I was not afraid to say that to her in her position. She's always been one to empower, to challenge, and to say, 'Don't just listen to me for what I have to say. You have a voice. I want to hear your perspective and your voice as well.' She's become an incredible mentor to me over the years. I miss her so much at work, but I'm grateful we stay connected.
What advice would you give to young women entering your industry?
Never stop learning. Always take time to seek out what's new in the industry. Have that growth mindset to continuously learn, to continuously build your skills, because if you tell yourself that you've learned everything that you think you've needed to learn, then that's not growth. We're never old enough to enhance our skills. And then there's one of my favorite quotes from Maya Angelou that I live by: people will remember what you've said and what you've done, but they'll never forget how you make them feel. When I think about leadership especially, which is a passion area of mine in terms of training in our organization, I focus on the importance of emotional intelligence and empathy and compassion in your leadership style. At the end of the day, it's really the people that help to drive the initiatives and the outcomes. The tasks will get done, but the people is what's truly important. I always say that as a leader of my team, I always have the opportunity to stand up and take the bow, but if it's not for my team, I would not be able to do that. You want to be that type of leader that 5, 10 years from now, when they're talking about their best boss or their best leader, it's you. It's the way you made them feel.
What are the biggest challenges or opportunities in your field right now?
Right now, we're spending a lot of time on AI implementation. We're working to devise plans to help our employees learn the different tools and technologies associated with AI. It's a significant focus for us, along with leadership development and employee development. We're constantly looking at how to help our organization adapt to these new technologies while continuing to develop our people.
What values are most important to you in your work and personal life?
From a personal perspective, I used to be that shy, quiet, introverted person. I was a very obese child, teenager, and adult, and over the years I've gone through a health journey and physical transformation. I've lost 245 pounds. I'm also a two-time cancer survivor. I just finished chemo in November, and I'm now in remission. I've gone through a lot in terms of my personal journey, and I've been bullied. I want to be that person who can help empower and inspire other women in this community to say, 'Hey, we all go through a lot personally, and sometimes we carry it really well. We show up with a smile on our face, and nobody will ever know that you're going through what you're going through.' I want to be that person to say it's okay to show up and you might not be at your 100% today, but if you show up and give it your 80%, then that's okay. We all go through personal trials and tribulations and struggles, and that's one of the reasons why I want to put myself out there, to show that through trials, through adversity, through personal challenges, you can still succeed in your role. I also do mission work with an organization called Mission of Grace, an orphanage in Haiti. I've traveled there on numerous occasions to bring supplies and mentor teenage and younger children. That's definitely a passion project of mine, though I haven't been able to visit recently due to political unrest, but I still stay very connected to the organization.