CXO Outlook www.cxooutlook.com is a global knowledge sharing digital platform published by Connecta Innovation Private Limited. All rights reserved. The opinions expressed in the content and pictures provided are those of the authors. They do not purport to reflect the opinions or views of Connecta Innovation Private Limited or any of its members and we do not assume any responsibility. The publisher does not assume any responsibility for the advertisements, its content, pictures, and all representation of warranties made in such advertisements are those of the advertisers and not of the publisher. CXO Outlook www.cxooutlook.com is a Free Subscription and Free-to-read digital platform strictly not for sale and has to be strictly for internal private use only. Publisher does not assume any responsibility arising out of anyone modifying content and pictures, printing a copy of this digital platform in any format and in any country and all matters related to that.
The Rise of Women Who Lead: A Movement, Not a Moment
Afew weeks ago, I was sitting across from a friend— an accomplished entrepreneur—at a crowded café. Between sips of coffee and stories of juggling teams, clients, and toddlers, she smiled and said, “You know, sometimes I don’t even realize I’m the only woman in the room—until I do.”
That moment stuck with me.
Because here’s the thing: women are showing up everywhere—in boardrooms, behind startups, at the helm of global companies. They’re not just taking seats at the table—they’re redesigning the table entirely.
Still, it’s not always smooth sailing. Gender bias? Still there. Unequal access to funding? A frustrating reality. And leadership roles? Let’s just say we’ve got room to grow. But there’s good news—real, tangible change is happening. Technology is leveling the playing field. Companies are
finally treating diversity and inclusion not as checkboxes, but as business essentials. Mentors are stepping up. Workplaces are becoming more flexible. It’s not perfect, but it’s progress. And it’s powerful.
This issue of CXO Outlook is a celebration of that progress. It’s our tribute to the women
leading change—not with loud fanfare, but with quiet grit and unstoppable vision. Our cover story features Yolanda Perez, Senior Vice President and International Wealth Advisor at Truist Wealth. She’s spent nearly two decades guiding clients across North America and Europe, and her story is as inspiring as it is insightful.
From finance to tech to entrepreneurship, this edition brings together voices of women who are rewriting the rules—and lifting others as they rise. If you’ve ever wondered what leadership looks like when it’s fueled by empathy, driven by purpose, and unafraid to challenge the status quo—this one’s for you.
So, here’s a question: What kind of future are we building, and who gets to lead it? At CXO Outlook, we believe the answer should be—everyone. And especially, more women.
Enjoy Reading.
Sarath Shyam
Perez SENIOR VICE PRESIDENT, INTERNATIONAL WEALTH ADVISOR, TRUIST WEALTH
BRIDGING THE FINANCIAL LITERACY GAP
Yolanda
18
Roxana Sosa Ortiz
Redefining Leadership in Global Logistics CEO of Tripp Cargo Logistics
MOST INSPIRING BUSINESS WOMAN 2025
IN
MY VIEW
Diana Morales, Founder & Principal CEO, DM Consulting Pioneering the Future of Biotech
28
Flexibility Redefined: Strategies for Thriving in a Dynamic Career Landscape
Elizabeth Willetts, Founder and CEO, Investing in Women, Author of Flex: Smart Strategies to Build a Successful Career Around Your Life Pioneering New Frontiers in Employee Benefits & Risk Management
Andrea Baldrica, Chief Sales Officer-Colorado, HUB International
Transforming Retail Through Innovation
Paula Rosenblum, Co-founder, RSR Research
Building Trust with Customers: A Strategic Imperative for C-Suite Executives
Melissa Fors Shackelford, Marketing Leader & C-Suite Advisor
COVER STORY
Yolanda Perez
SENIOR VICE PRESIDENT,
INTERNATIONAL WEALTH ADVISOR, TRUIST WEALTH
BRIDGING THE FINANCIAL LITERACY GAP
Yolanda Perez is a Senior Vice President and International Wealth Advisor at Truist Wealth, where she is responsible for the development of relationships with international individuals, families and companies. Yolanda has over 18 years of experience working with high-net-worth clients in various roles throughout her career in North America and Europe. She serves as a Trust and Estate Practitioner (TEP) and is a member of numerous organizations, including the Finance & Investment Committee of the Broward College Foundation Board and the Planned Giving Advisory Board for the University of Miami. She is also Regional Director for LATAM for the Hedge Fund Association and a member of Lives Amplified.
Yolanda is passionate about financial literacy education and has done seminars and workshops for professional athletes in various sports and for organizations, such as the Miami Marlins, Minnesota Twins and Philadelphia Phillies. In 2023, Yolanda won the Wealth Management Award during the 7th Annual Whealth and Innovation Awards; an annual award that honors women leaders and executives during International Women’s Day. She is also the co-founder of the MiamiDubai Chamber of Commerce, established in 2024.
Recently, in an exclusive interview with CXO Outlook Magazine, Yolanda shared her inspiring journey into wealth management, insights on the role of mentorship in professional development, the secret mantra behind her success, future plans, pearls of wisdom, and much more. The following excerpts are taken from the interview.
Hi Yolanda. What inspired you to pursue a career in wealth management, and how did you break into the industry?
There are so many inspiring and challenging aspects of wealth management. It allows me to connect with clients, to travel the world and keep
up with financial trends. It also enables me to help families secure their legacy and support the next generation. Wealth management is not an easy career to break into it and there is no exact path. I applied to a banking position in NYC for a French speaking private banking
My role allows me to think outside the box and connect with clients through meaningful interactions
role at a top US bank in 2006. I was incredibly lucky and blessed to start my career at a Tier 1 financial institution. That role helped me open doors to future roles in various parts of the world and led me to work in Investment Banking and Wealth Management.
What do you love the most about your current role?
I love to know that the work I have done truly impacts clients and families in a positive way. To understanding their business model and help create an infrastructure for clients, means that they can secure their family legacies for years to come. I am always learning and challenging myself to find creative solutions. Trends, laws and the political & financial climate is always changing and adapting to help those around me be successful and live better and more efficient lives is very rewarding to me. My role also allows me to think outside the box and connect with clients through meaningful interactions. I get to know what keeps my clients up at night and I try to ease their fears and give them hope.
How do you approach financial literacy education for professional athletes, and what unique challenges do they face in managing their wealth?
The life of a professional athlete is distinct. Athletes come from diverse backgrounds and need a lot of support to launch their professional careers. While they need to focus on their craft, they also need a dedicated team to help them achieve their success in various ways. More than often, they do not have any financial experience, and have an entourage that they are supporting, which includes family and friends. Learning to manage their wealth is key early on and ideally before their professional contracts are signed. Providing financial literacy education empowers athletes to take charge of their careers and keep their retirement earnings intact. Oftentimes, they face bankruptcy or do not have any earnings left post-career due to financial mismanagement. It
is key to help set them up for success early on to take better decisions.
How do you balance your professional responsibilities with your commitment to community service and philanthropy?
I acknowledge that my professional responsibilities are important, because they can potentially impact the lives of the families I serve. I am therefore careful to add outside volunteer activities because they demand crucial time and attention. I was very privileged growing up to have had a great education and enough resources to grow my career. As experienced professionals we all have a responsibility to give back to the communities we serve in some shape or form. I also ensure to balance my personal family life because my children are incredibly important to me. By conducting community service, I can help guide the next generation and help others succeed. It also makes me feel that I am leaving the next generation the tools they need to find abundance and purpose.
What role do you believe mentorship plays in professional development, and how have you benefited from mentorship in your own career?
There are many layers to mentorship. Mentors are people that we learn from and emulate as we try to unlock the art of their genius. The secret sauce that makes them so interestingly profound and achieve things with ease. I have had various mentors, both men and women, throughout my professional life, cloaked with integrity and finesse, that I still deeply respect and can call to consult. As leaders of their field and expertise, I am blessed to have found them and hope to pay the learning forward to those newly starting their careers and needing some
help navigating their professional lives. If I can share one valuable learning with another, then I feel honoured and content.
You were recently recognized as one of the Top 50 Women Leaders of Miami for 2025. Our readers would love to know the secret mantra behind your success. I decided long ago that no matter what happens to live life to its fullest. That every day, is a new day, where I can put one foot in front of the other with purpose and conviction. If I can sleep well, it is because I carry my life with authenticity and honesty. I treat my clients with care, as if I would my own family. I live with integrity, and I am able to manifest abundance through positivity and kindness. By remaining humble, I am able to connect with others and find creative solutions that others may not necessarily see or imagine. If I work with high expectations and towards excellence, then I can also influence others by setting a good example, which enables them to raise their bar and exceed their own standards.
How do you keep your mind healthy and stay resilient? And how do you motivate your team?
A healthy body and environment nurture a healthy mind and spirit. I eat a balanced diet, and I exercise regularly. I take walks in nature and listen to positive podcasts to raise my spirit, give me hope and strengthen my determination to achieve my goals and objectives. I am also able to stay resilient when I face resistance or push back on some of my pursuits. I believe there is always a solution and set both shortterm and long-term goals. While I prefer to motivate others, by setting a good example,
I provide honest and constructive feedback, suggestions and always cheer people on. I am quite pleased by the success of others, and I am always happy to share my success. There is no “I” in team, and without a robust support system, the team could not function to reach its capacity or achieve excellence.
Is there a particular person you are grateful for who helped get you to where you are?
I am grateful to many people as it has been a long road. My grandmother was the first businesswoman I ever met. In her thirties, she was an executive at a Swiss firm in Peru and had to navigate her professional life during a time period that was not particularly favorable to women. She was elegant, classy, professional, brilliant, intentional with her words and very kind. If you were in her presence, she would make you feel like you were number one. I aspire to make others feel empowered, the same way she could make others feel. By elevating others, I am able to honor her and my family legacy.
What do you hope to achieve in the next 5-10 years, and how do you plan to get there?
In the next ten years, I hope to either be promoted to the next phase in my career, by leading a larger group within my institution, or alternatively branching out and managing my own firm. I would also love to write a book, learn a new language, buy more real estate and travel to new places around the world. I have always wanted to go to Kyoto in Japan and also see the Aurora Borealis. I also recently established a chamber of commerce
My ultimate plan is to reverse engineer my plans, to imagine the short and long terms outcomes I would like to achieve, then figure out what strategic plan I need to create to get me there
and would like to see it scale and help others grow their businesses. My ultimate plan is to reverse engineer my plans, to imagine the short and long terms outcomes I would like to achieve, then figure out what strategic plan I need to create to get me there.
What advice would you give to aspiring women leaders in finance, and what challenges do you think they may face?
Even in 2025, finance is still a male dominated field. I would advise aspiring women leaders, that if you want a seat at the table, you will sometimes need to add a new seat to it, because there may not necessarily be a placed created for you. While we all
sometimes need validation to ensure we are doing the right things the right way, be assertive, be courageous and if you are right, then tell the truth, do right by others and to yourself. Learn how to lobby, negotiate, manoeuvre, and hold your ground when needed. Be easy to work with, be kind, humble and no matter what it is a small industry; you will always see the same people. Your reputation will follow you, so it is important to stay on good terms with others. One minute you could be the leader and the next, it can be your subordinate in the same or another firm. Finally, work the hardest, expect the least and prioritize your family always. Family always comes first, and no employer should make you feel guilty for that.
MOST INSPIRING BUSINESS WOMAN 2025
Roxana Sosa Ortiz
CEO OF TRIPP CARGO LOGISTICS
REDEFINING LEADERSHIP IN GLOBAL LOGISTICS
Roxana Sosa Ortiz, CEO of Tripp Cargo Logistics, didn’t just step into the logistics industry; she immersed herself in it. Thirty years ago, she started as a sales manager, handling everything from customer interactions to service proposals, order management, and delivery coordination. Over time, she discovered something powerful: she had a knack for creating strategies that optimized operations, boosted efficiency, and, ultimately, increased sales and profits. As her expertise grew, so did her reputation. Companies from around the world began to trust her leadership, relying on her to handle shipments to and from Costa Rica. “I became
that person whom other international agencies trusted to put in my hands the receipt of their loads for delivery,” she recalls. With each successful transaction, her role expanded, and soon, clients weren’t just sending her business— they were encouraging her to start her own.
At first, she hesitated. But then came the defining moment: Why not build something of my own? It was a question she couldn’t ignore. With the unwavering support of her husband and mother, she took the leap and founded Tripp Cargo Logistics.
“Today, I do not regret this turn. I love it and am passionate about it,” Roxana says. “Helping companies bring their goods into the country
ROXANA SOSA ORTIZ, CEO OF TRIPP CARGO LOGISTICS
and seeing them successfully placed in the market brings me joy. I love what I do, and I do it with passion.”
Leading with Service, Not Just Rates
Before founding Tripp Cargo Logistics, Roxana spent years working in international cargo transportation and logistics, gaining firsthand experience in what truly drives business success. She quickly realized that while pricing matters, it’s an exceptional service that wins and retains customers. “Most customers are won by the service-rate mix, not just by the rate,” she explains.
That belief became the foundation of Tripp Cargo Logistics. Roxana set out to build something different—more than just a transportation company. “We go beyond that. We guide, advise, and provide logistical solutions. We have become strategic allies, keeping our clients informed with timely updates on international and national affairs so they can make better decisions about their shipments. This hands-on, personalized approach has given Tripp Cargo an edge in an industry where uncertainty is the norm.
The logistics landscape, especially after the pandemic, has become increasingly complex. With changing regulations and fluctuating shipping guidelines, keeping cargo moving efficiently requires constant adaptation. Tripp Cargo remains ahead by continuously innovating and finding ways to bring shipments into Costa Rica on time, despite the challenges.
“Most customers leave because of poor service, not pricing,” Roxana emphasizes. Her leadership is rooted in problem-solving, eliminating roadblocks that hinder efficiency and fostering strong, trust-based relationships with clients, suppliers, and employees alike.
Through strategic leadership and a deep commitment to both family and business, Roxana is ensuring that Tripp Cargo Logistics not only thrives today but continues to grow for generations to come
Taking the Leap and Building a Legacy
Starting a business is never easy but doing it while raising two children adds another layer of complexity. Roxana faced three major challenges: leaving a stable job with a fixed income, securing the capital needed for daily operations, and breaking into a highly competitive and heavily regulated market. “We faced these challenges with wisdom and a lot of hard work,” she says.
Balancing a family business with longterm sustainability is an ongoing effort— one that requires constant attention. At Tripp Cargo Logistics, family and business are deeply intertwined. Roxana’s husband serves as the general manager, her daughter oversees pricing, and her son, who recently joined, works as an accounting assistant. Both children have already earned business
administration degrees and are now learning the ropes firsthand.
For Roxana, education is just the starting point. “Even though they are university graduates, they must start from the foundations of the company—pricing and finance—so they understand its roots. That’s how they will become true leaders and continue our legacy.”
Despite working side by side as a family, professionalism remains a priority. “When we are at work, we are colleagues and subordinates, aware that we share a unique socio-business structure with values and challenges different from other organizations,” she explains.
Through strategic leadership and a deep commitment to both family and business, Roxana is ensuring that Tripp Cargo Logistics not only thrives today but continues to grow for generations to come.
The Power of Customer-Centric Service
In the transportation and logistics industry, success is built on more than just efficiency— it’s about relationships. At Tripp Cargo Logistics, exceptional customer service isn’t just a priority; it’s the foundation of everything they do. Roxana emphasizes this approach: “We have a dedicated team committed to providing our clients with the best attention, efficiently tracking their shipments, advising them, and being responsive to their calls, messages, and emails for any inquiries they may have.”
Going beyond standard service, Tripp Cargo offers personalized consulting to help clients find the best logistics solutions tailored to their specific needs. This commitment to collaboration ensures that both the company and its clients grow together.
Going beyond standard service, Tripp Cargo offers personalized consulting to help clients find the best logistics solutions tailored to their specific needs
With a vision of becoming a globally recognized logistics provider, Tripp Cargo remains steadfast in its core values: respect, honesty, transparency, passion, service quality, customer orientation, and social responsibility. These principles guide every decision, fostering strong partnerships and a reputation for reliability.
Excellence Rooted in Ethics and Expertise
The Tripp Cargo Logistics team understands that true service quality comes from exceeding customer expectations, not just meeting them. This means offering quick responses, timely problem resolution, and a tailored approach to each client’s unique needs. Experience and a positive attitude are at the heart of this customer-first philosophy.
Ethics plays a central role in the company’s leadership, which is deeply embedded in the Sosa Ortiz family. “We have always led with honesty and integrity, setting an example for our team to show that ethics is a priority in the organization,” Roxana explains. By modeling these values, leadership ensures that integrity is woven into the fabric of the business.
To reinforce this commitment, Tripp Cargo maintains a continuous training program, ensuring that its team stays ahead of industry changes and best practices. In addition, their quality policy guarantees timely advice, clear communication, and a proactive approach to client needs. By keeping detailed client profiles and fostering ongoing dialogue, the company maintains strong relationships built on trust and accountability.
The Spirit of “Pura Vida” in Business
In Costa Rica, the phrase “Pura vida” is more than just a greeting—it’s a way of life. It embodies positivity, resilience, and an open-hearted approach to the world. Tripp Cargo Logistics embraces this spirit in its business philosophy, reflecting the country’s commitment to dialogue, inclusivity, and environmental consciousness.
As a company that works with suppliers across the globe, Tripp Cargo maintains warm and respectful relationships, embodying the values of Costa Rican culture. “We ‘Ticos’ believe in building strong, honest connections, no matter where in the world we do business,” Roxana shares.
This approach has helped the company navigate the complexities of international logistics while maintaining the Pura vida mindset—one that balances hard work with
optimism and a deep respect for people and the planet.
Innovation That Drives Confidence
In logistics, innovation isn’t just about adopting new technology; it’s about creating real value. Tripp Cargo Logistics has mastered this by integrating systems that provide full operational control, from shipment initiation to final delivery. This ensures the best transit times, competitive pricing, and unwavering security.
One of the company’s key strengths lies in its ability to anticipate and manage global logistical disruptions. “We guide, inform, and advise on possible international situations that may impact logistics,” says Roxana. “But when you have real-time data, you can make decisions that safeguard your delivery commitments.” This proactive approach has
Tripp Cargo Logistics has mastered this by integrating systems that provide full operational control, from shipment initiation to final delivery
earned Tripp Cargo the trust of the market, establishing the company as a reliable business partner in cargo management.
A standout feature of Tripp Cargo’s customer experience is its dedicated Call Center. Staffed by a bilingual team, it provides end-to-end personalized support—coordinating pickups, monitoring inland shipments, generating warehouse arrival reports, tracking itineraries, and keeping suppliers in Costa Rica connected. This hands-on support allows logistics managers to focus on strategic operations while Tripp Cargo handles the intricate details of their shipments, whether by air, sea, or land.
Overcoming Industry and Generational Challenges
Every industry faces hurdles, but in transportation and logistics, two key challenges stand out for
Tripp Cargo. The first, an external obstacle, is the country’s lagging port infrastructure—an issue that affects Costa Rica’s entire export and import sector. “Our ports are practically at capacity, making it a critical point for international trade,” Roxana explains. As a Director of the Costa Rican Chamber of Commerce, she actively contributes ideas and policy suggestions to drive infrastructure modernization, aiming for a future where Costa Rica boasts first-world logistics capabilities.
The second challenge is succession planning—ensuring the successful transition of Tripp Cargo’s leadership to the next generation. As a family-run business, integrating the younger generation into operations is essential for long-term continuity. “The process of incorporating our children into the business is something we are already working on,” Roxana
shares. This transition isn’t just about passing the baton—it’s about equipping future leaders with the knowledge and skills to carry the company forward.
With a proactive approach to both industrywide and internal challenges, Tripp Cargo is positioning itself for a future defined by growth, resilience, and innovation.
Building Global Alliances for Lasting Success
At the heart of Tripp Cargo’s success is strategic collaboration—strong relationships with transportation and logistics providers that extend across national and international borders. Roxana Sosa Ortiz believes that these alliances are a cornerstone of the company’s achievements. “We maintain daily communication with our business allies, visit them personally in their offices across different regions, and attend several conventions annually,” she explains. These meetings aren’t just about business; they’re about building trust and negotiating from a win-win perspective, ensuring mutual benefits for all parties involved: Tripp Cargo, its partners, and its clients.
With an expansive network spanning 198 countries, Tripp Cargo has solidified its global presence. Its 8,500+ offices worldwide serve as critical hubs, ensuring seamless cargo management to and from Costa Rica. This level of connectivity allows the company to provide clients with reliable, efficient logistics solutions, no matter the destination. By fostering international partnerships and prioritizing relationship-building, Tripp Cargo isn’t just moving shipments; it’s moving the industry forward.
Breaking Barriers and Building Bridges
Success is rarely a solo journey, and for Roxana, strong mentors, and strong support have played a crucial role in shaping her leadership path. From the very beginning of Tripp Cargo, she was fortunate to have the backing of four influential men: her husband, Juan Carlos Agüero, and her mentors, Daniel Yankelewitz and Carlos Rodríguez—both of whom have since passed away—as well as international mentor David Kassin, a respected Colombian businessman.
For nearly a decade, Roxana has served as the President of the Customs Commission of the Chamber of Commerce of Costa Rica, a position traditionally held by men. While transportation and logistics remain male-dominated industries, she firmly believes that expertise, experience, and self-confidence can dismantle gender barriers.
Her advice to women aspiring to leadership roles is simple yet powerful: invest in education and training within their chosen field because, as she puts it, "knowledge is power." She also emphasizes the importance of seeking mentors, regardless of gender, who can provide guidance, encouragement, and opportunities. "Surround yourself with people who believe in you and support your goals," she advises. Additionally, she encourages women to actively participate in industry organizations, not only to expand their network but also to deepen their understanding of the political, social, and economic forces shaping their sector.
Finding the Balance Between Business and Family
Running a family business presents a unique challenge: where does work end and personal life begin? For Roxana, maintaining balance requires intentionality. "It’s not easy when you
Tripp Cargo’s legacy is more than just a successful logistics company; it is a benchmark for customer service excellence, ethical business practices, and industry leadership
share both the workplace and home with part of your team," she acknowledges. Yet, she has found ways to create space for both.
Annual vacations are sacred family time—an opportunity to disconnect from work, clear their minds, and focus solely on each other. Even during business trips, she ensures that at least two or three days are set aside to explore the local culture, take in the sights, and enjoy the moment.
Though she is always a CEO, she also prioritizes being a woman, a wife, and a mother. "Leadership doesn’t mean sacrificing your personal identity," she says. By establishing boundaries and dedicating time to each aspect of her life, she proves that a thriving career and a fulfilling personal life are not mutually exclusive.
The Legacy of Excellence and Impact
Tripp Cargo’s legacy is more than just a successful logistics company; it is a benchmark for customer service excellence, ethical business practices, and industry leadership. With numerous international awards recognizing its contributions across various sectors, the company stands as a testament to what dedication, hard work, and unwavering commitment can achieve.
Beyond business success, Roxana sees Tripp Cargo’s greatest impact in its influence on people— its employees, its clients, and even Costa Rica’s economic landscape. "We have built something that doesn’t just serve our clients but also uplifts our team and contributes to our country’s growth," she reflects.
The future of Tripp Cargo isn’t just about expansion; it’s about maintaining the high standards, integrity, and customer-first mindset that have defined its journey. That, Roxana believes, is the true legacy—one that will inspire and guide the company for generations to come.
Pioneering the Future of Biotech
Diana Morales, Founder & Principal CEO, DM Consulting
Hi Diana. What inspired you to establish DM Consulting Services, and what unique value proposition do you offer to clients?
My inspiration for founding DM Consulting stemmed from various experiences, particularly over the last four years of my career. I observed a significant lack of culture, leadership, and
expertise within startups and emerging biotech companies. Many of these companies are spin-offs from venture capital firms or are run by individuals with financial backgrounds, leading to numerous mistakes. As they reach the expansion phase, they often realize they've missed crucial years of strategic planning and forward-thinking, which hampers their growth or leads to failure.
Diana Morales, Founder and CEO of DM Consulting Services, brings over 25 years of experience in the bioprocess, cell, and gene therapy sectors, offering bespoke strategies for biotech startups and clinical drug development firms. At DM Consulting Services, Diana's leadership focuses on crafting robust commercial strategies and sales organizations for emerging companies, driving scientific innovations to market success with adaptability and a customer-centric approach.
Previously, Diana held significant roles at OrganaBio, Mass Biologics, Invetech, GE Healthcare, and Thermo Fisher Scientific. At OrganaBio, she served as Vice President of Sales, where she played a pivotal role in advancing cGMP manufacturing services for cell-based therapies. As Vice President of Business Development and Operations at Mass Biologics, Diana contributed to the development and manufacturing of vaccines and biologics, emphasizing operational excellence in this historic institution. During her time at Invetech, Diana led the launch of new GMP products and services as VP, Head of Cell Therapy Products & Services. Her leadership in global management and team building significantly bolstered Invetech’s presence in the market.
Recently, in an exclusive interview with CXO Outlook Magazine, Diana shared her professional trajectory, insights on the importance of diversity and inclusion, the secret mantra behind her success, personal hobbies and interests, future plans, pearls of wisdom, and much more. The following excerpts are taken from the interview.
Network, network, network and always learning new skills, whether it is AI tools and technology or new ways of doing business in the new era
To address this, I established a network of former C-suite executives and subject matter experts with diverse expertise. Combining their knowledge with my business development and commercial experience, we can guide any startup to success and support them throughout their journey until they no longer need our services. Our model primarily serves clients in Series A to C funding stages.
What role do you think data analytics and digital technologies will play in shaping the future of the biotech industry?
I believe it will play a huge role as things are shifting and digitalization is at the forefront of innovation. We need to figure out how to keep up with all of it but most importantly how we prepare the agencies and FDA to follow
Have a vision of what you want to represent to the world and who do you want your company to be knows as 5 years or 10 years out
through and act quickly to help therapies to market quicker.
How do you stay up to date with the latest developments and advancements in the field?
Network, network, network and always learning new skills, whether it is AI tools and technology or new ways of doing business in the new era.
What are your thoughts on diversity and inclusion in your field? How important is it to have authentic conversations with leaders, professionals, and changemakers to create more acceptance across the globe?
I have not seen diversity to be an issue in my field. It is critical however, that leaders are leading with transparency and an appetite for their teams to grow professionally. We need the new generation to be prepared for what they will be needing to lead with in the future. We need to build changemakers and allow for inclusion of opinion within the workforce.
You were recently recognized as one of the Top 50 Women Leaders of Connecticut for 2025. Our readers would love to know the secret sauce behind your success.
I have been honored three times by Women We Admire: as a Top Leader of 2024 nationally, and as a Top Leader in Connecticut and Massachusetts in 2025. This recognition has been incredibly humbling. The key to my success lies in authenticity, resilience, and perseverance through life's challenges. I maintain the same high standards and ethics both at home and at work, and my faith has been a significant guiding force. I have always believed that God had greater plans for me, and I have strived to follow the path intended for me.
If you could have a one-hour meeting with someone famous who is alive, who would it be and why?
Matthew McConaughey… He is someone that has always intrigued me with how he manages his personal life and professional life. Most down-to-earth person, someone who would
shake the janitor’s hand and you wouldn’t be able to tell who he was. Treating others like he would want to be treated.
Is there a particular person you are grateful for who helped get you to where you are?
My parents, Thomas and Violet. The most amazing people in my world, my mentors, my biggest cheerleaders. I would not be here without them. Also, my husband Mike, who has been there throughout my journey.
How do you keep your mind healthy and stay resilient? And how do you motivate your team?
I meditate, work out and always explore new adventures with my family. We love to travel to different places and make new memories. I love seeing my children happy so whatever they want to do I am always game to try something new.
What do you hope to achieve in the next 5-10 years, and how do you plan to get there?
Build and scale up my company nationally. I have some big plans and vision of where I see DM Consulting fitting in the world of biotech and biopharma. We will be the go-to up and coming boutique consulting firm for startups.
What advice would you give to emerging leaders in the biotech industry?
Plan ahead and prepare for the type of culture and company you want to build. Have a vision of what you want to represent to the world and who do you want your company to be knows as 5 years or 10 years out. Build your commercial strategy along your science. These go hand in hand, and they are not separate. You will miss the mark if you don’t plan for this along your journey.
Pioneering New Frontiers in Employee Benefits & Risk Management
Andrea Baldrica, Chief Sales Officer-Colorado, HUB International
Hi Andrea. Please tell us about your background and areas of expertise. I started in Employee Benefits in 2001 right after 9/11, with a small agency owned by my step-dad, and within a couple of years I decided it was the career that I wanted. We created a plan so that I could buy-out my step-dad, which I completed in 2008. At that point I focused on small group benefits in Colorado, and worked for several years to grow the agency. At some point I realized I wanted to work with more complex accounts, but I knew that I did not have the resources to move up-market and
there was only so much that I could outsource while maintaining profitability. In 2012 I made the decision to pursue an Executive MBA, and through that education and in talking with mentors, it seemed like the right time to sell my agency. I sold in 2014 to HUB International. It was a successful transition, and I qualified for our Leader’s Club, SHARP, within my first year and for the subsequent years. I developed expertise is multiple funding options and focused on multi-state and multi-national employees.
I love unions, multiple plan structures, and challenges. The more complex the better!
Thinking through the approach and people to include in meetings is fun when it leads to success
As Chief Sales Officer for HUB Colorado, Andrea Baldrica guides the team to ensure target completion as well as exceeding client expectations. In 2014, Andrea sold her agency to HUB International and came on as the Colorado Springs Practice Leader. In 2019, she was named the Chief Sales & Strategy Officer, guiding all lines of coverage to develop and execute sales strategy for HUB. When working with clients, Andrea focuses on multi-state and global organizations. Andrea brings her expertise in self-funding, direct provider contracting, captive management and pharmacy contract utilization to drive actionable strategies that bend cost curves, reduce risks, and improve employee satisfaction.
Born and raised in Colorado Springs, Andrea is passionate about the community. She has served on the board of directors for the Southern Colorado Chapter of Health Underwriters, The Southern Colorado Chapter of the American Red Cross, and the Children’s Literacy Center. Additionally, she has served on the national broker advisory boards for several insurance carriers and speaks regularly on health care and insurance trends. Andrea has a BA from The Colorado College, and an Executive MBA from the University of Colorado. She has continued her education with Leadership Pikes Peak, and on-going leadership and industry classes. She is fluent in Italian and is passionate about Italian culture, as well as traveling with her kids and husband.
Recently, in an exclusive interview with CXO Outlook Magazine, Andrea shared her professional trajectory, insights on diversity and inclusion, the secret mantra behind her success, her favorite quote, future plans, pearls of wisdom, and much more. The following excerpts are taken from the interview.
Having the resources that at the time a top ten brokerage could provide was a gamechanger for me. In 2019 my mentor took over as our president and asked me to become our Chief Sales Officer. Leadership was always something that I wanted to eventually get to, and I was ready to make the shift. I’ve been the Chief Sales Officer for Colorado, for six years, overseeing Employee Benefits, Retirement & Private Wealth, Property & Casualty, and Personal Lines.
What do you love the most about your current role?
I love strategizing with our sales team to win new clients! Thinking through the approach and people to include in meetings is fun when it leads to success. I also love the challenge of helping my teams work through complex situations and position themselves to win. It is extremely rewarding to mentor people and seeing them improve and grow.
What emerging trends or innovations excite you for the future of the insurance industry?
AI will change the way we all do business, and we are already seeing some dramatic impacts on our industry. It will improve claims predictability and forecasting will change the industry and way that we are able to manage our clients’ financial performance. It will be interesting to see how this plays out with regards to proactive measures that companies can take to mitigate high- cost claims.
I also expect to use AI more in forecasting sales and financial performance. This should help us run our businesses better and plan better for the future. The technology changes are so
rapid right now, that it is hard to predict what will come next.
What are your thoughts on diversity and inclusion in your field? How important is it to have authentic conversations with leaders, professionals, and changemakers to create more acceptance across the globe?
I think the industry has worked to improve on diversity and inclusion, but there I always room for improvement. Having diverse voices and backgrounds is essential for our industry to successfully serve our clients, but we also require a significant amount of expertise since we are responsible for consulting on our clients most precious assets. I think that we need to focus on youth so that we are able to develop interest in an industry that is not always seen as sexy. With our aging industry we need to continue our efforts to bring in a diverse workforce in all senses of. e word. Our clients are around the globe and have remarkably diverse workforces. If we don’t have a variety of perspectives, it is a disservice to our clients.
You were recently recognized as one of the Top 50 Women Leaders of Insurance for 2024. Our readers would love to know the secret mantra behind your success.
I don’t know that this is a secret, but I believe in being authentic and I think that has served me well. Whether it was in my role as a direct contributor or as a leader, I have always worked to bring energy and honesty to my interactions. My goal is that people leave every interaction knowing that I’m invested in their success.
It is amazing to make a good living knowing that you are helping others build and protect their most precious assets, but don’t let that responsibility intimidate you
I also had a mentor once tell me that the most successful people in sales minimize their “wallow” time when they lose a deal. I take that to heart and coach people that you can have a night to be down after a loss, but the next day is a new day and you have to put your past behind you and look to what great thing you can do that day. It has really helped my get back on the horse after a rough ride.
If you could have a one-hour meeting with someone famous who is alive, who would it be and why?
I think I’d like to interview Oprah Winfrey. I think she is an amazing inspiration, who came from nothing, as an unknown black female to one of the most successful and influential women of our time. Not only is the empire she has built something that is amazing, but equally inspirational is all the people she has carried along with her. I think we all have the
responsibility to pull others with us in our success so that we perpetuate success for future generations and those around us.
Is there a particular person you are grateful for who helped get you to where you are?
There are too many to count, but if I had to pick one it would be my husband who helped me overcome a lot of fear and believe in myself and abilities. I would not have made some of the career decisions that have gotten me to this point without being able to bounce ideas off him, talk through scenarios and feel the support that he has always given me.
How do you keep your mind healthy and stay resilient? And how do you motivate your team?
Having hobbies outside of work where I can draw energy from help me stay focused and
grounded. I exercise daily, love to cook, read and believe in taking a long vacation every year that allows me to recharge and come back excited to tackle what lies a head of me. Downtime and recovery are as important as going hard.
What is your favorite quote?
“What would I do if I weren’t afraid? And then go do it.” Sheryl Sandberg
Where do you see yourself in the next 5 years?
I want to continue to grow my impact on my community. I don’t know where I will be physically in five years, but I plan to be challenged, engaged and learning. I want to take on new projects and focus on learning. I’d like to continue to lead people and continue to grow an organization.
What advice would you give to anyone starting out on their career in your industry?
This industry can provide a life-long career or can be a stepping-stone- that is up to you but dig in and learn as much as you can for whatever the future brings. We live in a world of uncertainty, and we sell products to help protect against a lot of those uncertainties. It is amazing to make a good living knowing that you are helping others build and protect their most precious assets, but don’t let that responsibility intimidate you. There is a lot of fun and growth in what we do. Find a great mentor that you connect with and be intentional about your relationship with them to learn and grow. Finally, my best friends (including my husband) came from this industry. If you show up authentically and allow yourself to be open to honest conversations, you will develop amazing relationships that can serve you no matter where you go.
Wa n t t o S e l l o r fi n d
I nve s t o rs f o r yo u r
B u s i n e s s ?
Flexibility Redefined: Strategies for Thriving in a Dynamic Career Landscape
Elizabeth Willetts, Founder and CEO, Investing in Women, Author of Flex: Smart Strategies to Build a Successful Career Around Your Life
What inspired you to write Flex, and how did your experiences as a recruiter, entrepreneur, and career coach shape the book's core message?
Great question. I was inspired to write Flex after witnessing countless talented individuals, including close friends, struggle to find jobs they wanted and deserved just because they needed some form of flexible working. My 18 years working in recruitment exposed me not just to the rigidity of traditional work structures but also to a job market that often overlooks personal circumstances and penalises those
who want working arrangements that differ from the standard 9-5 norm. As the founder of Investing in Women, a recruitment business dedicated to championing flexible working, I've spent the past four years advocating for work arrangements that enhance both workplace productivity and job satisfaction. This book is a culmination of my mission to transform our approach to work, granting permission to those who might not want to work 40 hours a week by saying, ‘It’s okay—you’re not lazy or odd. You’re human.’ It's about creating careers that are as dynamic and varied as we are.
Many of us don't take the time to understand who we truly are - our strengths, values, and our definition of success
Elizabeth Willetts is the Founder of Investing in Women - a female-empowering job board and community helping family-friendly AND forward-thinking employers hire professionals looking for fulfilling flexible and part-time work. She is an experienced Recruiter with over 17 years of experience - both in-house at one of the Big 4 and from one of the UK's largest recruitment agencies. Elizabeth is also a mum to two daughters - Emily and Annabelle (and a Labradoodle called Dougal). She is a passionate believer in the power of part-time and flexible work to retain women in the workplace and close the gender pay gap. Her debut book, Flex - a dynamic guide for anyone wanting to build a successful career on their terms, came out in January 2025. In this exclusive interview, she shares powerful strategies from her book, inspiring reallife stories, and practical advice to help professionals align their work with their values. From overcoming imposter syndrome to crafting compelling flexible work proposals, Elizabeth’s perspective offers a fresh roadmap for navigating today’s challenges while fostering long-term career success. Her insights are not just a call for adaptability— they’re a blueprint for empowerment in the workplace.
The book is filled with real-life stories of women who overcame significant career challenges. Could you share one particularly memorable story that deeply resonated with you while writing?
My podcast interview with Rosie Reynolds, who is now the COO of the Financial Services firm Aspect Capital, was a particularly memorable interview that I couldn’t wait to share in Flex. Rosie’s story demonstrates the huge impact that mentorship and workplace support can have on your career. Despite her professional success, Rosie has grappled with imposter syndrome, feeling like an outsider in a world dominated by those from more privileged backgrounds. Her journey began in Scotland, where she trained as a lawyer, navigating her way through the competitive legal industry.
Mentorship changed the game for Rosie. Early in her career, a boss saw her potential and didn't just give her a chance—he actively backed her. This support didn’t just help her climb the ladder; it helped her believe in herself. Later, after having her fourth child, her employer stepped up again, funding coaching that helped her secure a pivotal leadership role on their board.
Rosie's experiences illustrate that overcoming imposter syndrome and other internal barriers often requires external allyship, mentoring, and support. They show just how powerful a supportive mentor can be for women to recognise their own value and take their place at the highest levels of their professions. Rosie’s experience plays a big role in Flex, where I talk about finding and using this kind of support to tackle our own career hurdles.
One of the standout promises of Flex is helping readers gain clarity on their career goals. What do you believe is the most common obstacle preventing people from identifying a job they truly love, and how does your book address it?
The most significant barrier I've observed that prevents people from getting a job they truly love is a lack of self-awareness. Many of us don't take the time to understand who we truly are - our strengths, values, and our definition of success. Without this self-knowledge, it's challenging to pursue a career that genuinely fulfils us as we’ll continue down a path of societal expectations or try to race to keep up with others - even if they are actually on a path we don’t fancy heading. In 'Flex', I tackle this head-on by guiding readers through insightful exercises and reflective questions that help them dig deep into their professional desires and personal values. The book is designed to give you the tools to uncover what you really want from your career, helping you to set clear, achievable goals and ultimately find joy and satisfaction in your career choices and professional life.
Flexibility in the workplace has become a hot topic in recent years. What are some practical strategies you recommend for making a flexible working request that employers are more likely to approve?
Flexibility at work is more than just a buzzword; it's a necessity for many of us juggling various personal commitments alongside our careers. In 'Flex', I dedicate a whole chapter to crafting a compelling flexible working request that your
employer is more likely to approve. It’s about making your needs resonate with the strategic objectives of your employer.
I guide you through creating a robust proposal, suggesting you start with a trial period to ease managerial concerns and demonstrate potential benefits such as increased productivity and loyalty. For example, the story of job-sharers Laura Walker and Chloe Fletcher in the book showcases how job-sharing not only fulfilled their personal needs but also dramatically boosted their professional output and satisfaction. Their success illustrates the mutual benefits of wellstructured, flexible work arrangements.
You emphasise that career progression is rarely a straight line. What advice do you have for readers struggling with feelings of failure or self-doubt during career disruptions?
Career disruptions don't have to signal a halt in your progression; rather, they can offer pivotal
moments for growth and self-reflection. In 'Flex,' I discuss how every disruption can be a hidden doorway to new opportunities. Take Jodie Mason, from Saint-Gobain, featured in the book, who wonderfully illustrates that career progress isn’t always a vertical climb—it can be sideways or even initially appear as a step back.
Jodie’s career journey moved from customer service to accounts, into credit services, and then circled back, but each move equipped her with even more invaluable skills and insights. She says, 'It's easy to feel that if you're not constantly climbing, you’re not progressing. But if you view yourself as a portfolio of skills and strengths, rather than just a job title, you open up new possibilities for yourself.'
If you’re feeling stuck or doubting your path, remember that disruptions are natural. They are not failures but chances to reassess and realign with your true career aspirations. 'Flex' provides strategies and stories to help you leverage these moments. By understanding
By understanding your unique strengths and how they fit into the bigger picture, you can navigate through career uncertainties with confidence and purpose
The secret to accomplishing a big project is simply to start. You can always refine and correct it later
your unique strengths and how they fit into the bigger picture, you can navigate through career uncertainties with confidence and purpose. Remember, adaptability and resilience are your most powerful tools for creating a fulfilling and successful career trajectory - no matter what that looks like.
Writing a book is no small feat. What was your creative process like while crafting Flex, and were there any surprising challenges or breakthroughs along the way?
Writing Flex while running a business and caring for two small children was challenging, but the process was surprisingly straightforward. I committed to a simple, manageable routine: thirty minutes of writing every day - often in the evening after my children had gone to bed. This wasn't about crafting a perfect draft on the first go; it was about consistency and progress. With Magic radio playing in the background and an Alexa timer set, I focused solely on getting the words out without editing as I went - I figured the actual writing would be the hardest part of the process. This approach helped me write 56,000 words more quickly than I anticipated. The real breakthrough came when I realised that the initial draft didn't have to be perfect.
Once all the content was on paper, refining and editing became less daunting. The secret to accomplishing a big project is simply to start. You can always refine and correct it later. This philosophy not only shaped my writing process but also underpins many of the strategies I share in "Flex," encouraging readers to take small, consistent steps towards big career goals.
Lastly, Flex is as much about resilience and fulfilment as it is about careers. What’s one personal mantra or piece of wisdom that has helped you stay motivated and balanced throughout your own journey?
One piece of wisdom that's always guided me is this: "The best time to plant a tree was yesterday; the second-best time is today." It’s a simple reminder that it’s never too late to start something new, to change direction, or to make an improvement. Whether focusing on my health, spending time with my family, or helping others with their careers, this belief keeps me pushing forward. It’s all about doing a little bit every day, building towards something great. This mantra isn’t just something I say; it’s how I live and is at the core of everything I share in Flex.
Building Trust with Customers: A Strategic Imperative for C-Suite Executives
Melissa Fors Shackelford, Marketing Leader & C-Suite Advisor
Trust has always been the foundation of successful customer relationships, yet in today’s challenging business environment, trust is more fragile than ever. Customers are growing more and more skeptical, questioning organizations’ motives, pricing practices, and commitment to transparency. For C-suite executives, building and maintaining trust isn’t just a theoretical goal, it can be a strategic advantage that drives customer loyalty, strengthens relationships, and differentiates companies in highly competitive industries.
Why Trust Matters in Customer Relationships
Trust is what turns one-time buyers into repeat customers and transactional relationships into long-term partnerships. It turns customers into customers-for-life. In business to business (B2B) models, trust ensures that clients see you as a reliable partner who delivers consistent value to them. In consumer channels (B2C), it’s what keeps your customers loyal when they have many other options and access to online reviews.
Across all industries, trust is continually tested by misinformation, inconsistent communication, and the appearance of solely profit-driven motives
Melissa Fors Shackelford is an award-winning healthcare marketing executive with over 20 years of experience driving growth initiatives. She has led transformative marketing initiatives for renowned Fortune 50, nonprofit and startup organizations. A recognized thought leader and sought-after advisor, Melissa is a frequent speaker and writer on healthcare branding and ethics. She was named one of the Top 50 Women in Healthcare in 2025, and earned the American Marketing Association’s Nonprofit Marketer of the Year award in 2019. Melissa holds an MBA from the University of St. Thomas and serves on multiple healthcare and advisory boards.
Across all industries, trust is continually tested by misinformation, inconsistent communication, and the appearance of solely profit-driven motives. By embracing transparency, consistency, and empathy, organizations can combat these challenges directly and position themselves as trusted leaders to gain competitive advantage.
Critical Pillars of Building Trust with Customers
Transparency: Customers want clear and accessible information. Whether it’s about pricing, processes, or company values, this openness builds trust and confidence. One example is Netflix’s approach to pricing where they openly communicate any price changes and provide clear reasons to justify the shift. This transparency reduces customer frustration and builds credibility.
Consistency: Trust builds over time through positive experiences with an organization. Consistency across your websites, apps, social media, and live interactions with your staff makes sure customers feel they can rely on your organization.
Empathy: Addressing customer concerns, fears, and aspirations demonstrates that you care. When communication reflects genuine appreciation and empathy, customers feel valued, which in turn creates stronger connections.
Practical Strategies to Build Trust with Customers
1. Combat Misinformation: Leverage social media and thought leadership to provide accurate, fact-based information. Partner with credible sources to counteract false narratives when necessary. For example,
By making transparency, consistency, and empathy foundational to your strategy, you can create deeper connections with customers, build loyalty, and position your organization as a partner they can rely on
a pharmaceutical company might collaborate with healthcare professionals to publish content combatting vaccine myths to build its credibility with customers.
2. Personalized Experiences: Use modern marketing tools to tailor communication to each customer rather than do mass communication. Personalization in follow-ups, recommendations, and communication shows customers they’re more than a number to you.
3. Authentic Storytelling: Share customer testimonials or behind-the-scenes stories to humanize your brand regardless if your model is B2B or B2C. Authenticity resonates in ways that generic sales pitches cannot.
4. Digital Engagement Tools: Meet customers where they are. Apps, portals, and personalized email campaigns make communication uniform and interactive. Two-way communication builds stronger relationships as customers can see that you are listening.
5. Proactive Problem Resolution:
Demonstrate a commitment to your customer’s satisfaction by addressing issues quickly. For example, some software companies proactively issue software updates to address performance issues, reassuring customers that they are valued. This proactive approach builds credibility, confidence and trust in the brand.
The Role of Trust in Brand Differentiation
In highly competitive markets, trust can set your organization apart. For instance, financial institutions like USAA are consistently ranked
among the most trusted brands due to their unwavering commitment to customer service, transparency, and clearly stated ethics. By making trust a core piece of your business strategy, your organization can create a unique position in the market that is a clear differentiator from the competition.
Furthermore, trust can have a direct impact on an organization’s profitability. According to the annual Trust Barometer study published by Edelman, 81% of customers say they need to trust a brand to buy from them. Companies that prioritize trust have higher customer retention rates, lower acquisition costs, and greater lifetime customer value. For C-suite executives at organizations in competitive markets, this reiterates the critical need to invest in building and sustaining trust as part of their overarching business strategy.
The Ongoing Commitment to Trust
Building trust with customers is not a one-time project; it has to be seen as a strategic priority. It requires actively listening to customer feedback, and constantly evolving to meet everchanging customer expectations. For C-suite executives, investing in trust is an investment in an organization’s long-term success. By making transparency, consistency, and empathy foundational to your strategy, you can create deeper connections with customers, build loyalty, and position your organization as a partner they can rely on. By prioritizing trust an organization will differentiate itself from its competitors.
In an era of skepticism, trust is one of your most valuable tools for strengthening relationships and driving sustained growth. By prioritizing trust, your organization can not only weather the challenges of today’s business environment but also thrive in the face of them.
Transforming Retail Through Innovation
Paula Rosenblum, Co-founder, RSR Research
Hi Paula. What drives your passion for the retail industry, and how has your perspective evolved over the years?
I’ve been in retail quite literally my whole life. My father was an independent clothing retailer and I used to go buying with him in the New York garment district (dating myself a bit here), and I’d also work in his store, and help him fill out his marketing postcards. So it’s fair to say that I’ve been soaking in retail for as long as I can remember. Of course, on a separate track, I studied programming and ended up as director of development in a midsized retail chain. That’s when I saw how much
technology can help the industry. There is the obvious: buying and selling merchandise, but there’s also the whole distribution process, the algorithms to decide what goes where and the financial processes, which are rather enormous in a large organization.
What do you love the most about your current role?
Well, as an analyst I don’t have to sing the glories of any one technology, I keep my finger on the pulse of the industry, help distinguish the real from the “bright shiny object” and best of all, I’m not involved in implementing anything.
Beyond machine learning, which has been used in the supply chain for some years, I truly believe AI is over-hyped in retail
Paula Rosenblum is co-founder of RSR Research and has consistently been recognized as one of the industry’s top retail technology analysts over the past decade. She is frequently quoted in major media outlets including the Wall Street Journal, Forbes, Washington Post, LA Times, NPR Marketplace and many others. She serves on the advisory boards of several retail technology vendors. Previous to her years as an analyst, she spent over 20 years as a retail technology executive and CIO at companies including iParty, Hit or Miss, Morse Shoe, Domain Home Fashions and others. Paula received her MBA in 1991 from Northeastern University, with a major in management of High Technology firms and was nominated to the Beta Gamma Sigma honor society. She’s active in a variety of organizations supporting human growth and development. Paula lives in Miami, Florida. Recently, in an exclusive interview with CXO Outlook Magazine, Paula shared her professional trajectory, insights on the role of data analytics and AI in retail technology, the secret mantra behind her success, future plans, pearls of wisdom, and much more. The following excerpts are taken from the interview.
Believe it or not, I occasionally miss being close to the action in stores, but mostly, I enjoy opining and separating the wheat from the chaff. I love being an advisor whose interests are solely for the company as a whole.
What role do you think data analytics and AI play in retail technology, and how can retailers effectively leverage these tools?
Data is one of a retailer’s most valuable assets and should be treated as such. Analytics have been critical for well over a decade. With Point Of Sale data in near real-time and more powerful computers, we can anticipate trends along with following them. At my company we have analyzed business intelligence for years and noted that the best performing retailers make the most use of analytics. Analytics tend to go viral in a company. You bring them in for one use case, and people start to find value and actually ask for more kinds of analytics as you go.
AI is another topic. Beyond machine learning, which has been used in the supply chain for some years, I truly believe AI is over-hyped in retail. On the customer facing side, I do believe satisfactory human to human interaction is really important. If AI was more mature, maybe our interactions with bots and scripted outsourced employees would be better. As it is, they’re a stumbling block to a good customer experience. I have often said if you want to get a sense of the real state of AI, call the customer service department of a company that claims its experience is powered by AI. You quickly learn it is not (reboot my modem again? Seriously???)
How do you advise retailers to approach digital transformation, and what steps can they take to get started?
As with all projects, it’s a good idea to start small, with projects that can be accepted by employees and don’t give the retailer too much risk. It’s time to get rid of those old COBOL and 4 GL languages for more extensible and flexible solutions. So, as with any project, start small and get some wins under your belt. This will build enthusiasm. I don’t think anyone loves the processes associated with eCommerce returns, customer service issues and lost inventory. So rather than going with “a big bang” go incrementally with, of course, cross-functional teams. Don’t let any one group dominate the conversation or the implementations. If you don’t have an IT Executive Steering Committee now, start one. It’s imperative and really did contribute to my success. The CIO must be relevant, and the management team should be walking in lockstep. This will help the rank and file get into it. Don’t assume that the IT team is any more forward thinking than anyone else. Definitely find a coalition of the willing. All my successes came when I lured people into a project with success and enthusiasm. All my failures came when people just weren’t interested. Cultural failures are real things, and they can destroy any project’s hope for success.
What are your thoughts on diversity and inclusion in your field? How important is it to have authentic conversations with leaders, professionals, and changemakers to create more acceptance across the globe?
It’s very hard to talk about DEI without getting political instantly. I want to try to avoid that
Be accessible, be kind, but on the other hand, don’t take any nonsense from anyone
here. I will say, it’s shocking for me that it’s even a conversation. There’s no doubt that we need to get more women involved in all kinds of STEM work. The political environment isn’t lending itself to that these days, but this observation comes from a childless cat lady who decided a long time ago that I couldn’t have it all. And business was where I wanted to focus. Do I think we need some form of quotas, or at least some form of data on how much diversity and inclusion we have in our organizations? Absolutely.
You were recently recognized as one of the Top Retail Experts of 2025. Our readers would love to know the secreta sauce behind your success. My company (RSR Research) likes to call itself the candid voice in Retail. I certainly fit in that category and have never been afraid to do 2 things: 1) call out technology as overhyped and not useful to business overall and 2) avoid acronyms, insider terms and overcomplicated explanations. The same skills that made me successful as a practitioner have made me successful as an analyst: candor, honesty, speaking in plain English and genuinely caring about the clients I’m working with.
If you could have a one-hour meeting with someone famous who is alive, who would it be and why?
I would love to have a meeting with Brian Greene, a physicist and author who has written spectacularly about attempts to reconcile the physics of the very large (relativity) with the physics of the very small (quantum mechanics). I can’t say it would help me in my career particularly, and I know I can’t do the math, but
the concepts are mind-boggling. I love being reminded that in this universe, we are neither the largest or the smallest entity. These are notions that keep me somewhat humble, and Mr. Greene writes and speaks in a way that the layman can understand. I really honor him. As you’ve probably figured out, I think we need to be well-rounded people!
Is there a particular person you are grateful for who helped get you to where you are?
I guess there are three in total. My father, who taught me the basics of retail by doing, rather than by teaching, my first retail CIO, Ray Benoit, who taught me how to manage and how to accept success, which was harder than I would have imagined, and finally, the late, great John Fontanella, who hired me as an analyst after I walked away from the world of being a CIO. I wasn’t buttoned down, or otherwise consultant-like for the traditional analyst role. But he knew the depth of my knowledge of retail and hired me over some other objections in the organization. It is sad to me that he passed on some years ago.
How do you keep your mind healthy and stay resilient? And how do you motivate your team?
I have been practicing meditation for over half a century, and it really does help me. I’ve also discovered that love and kindness go a long way. I don’t have a team per se at the moment, but these were things that always helped me and also helped me as an individual contributor. As an example, I had an employee who adored her horse. The horse
died and I gave her many days off to recover. My boss was furious at me, but I gained loyalty I might not otherwise have achieved.
Where do you see yourself in the next 5 years?
Mostly retired, though I’ve been asked a lot of times about writing a book about retail and the successful use of technology. I think about that a lot and it could well happen. I’ve certainly written enough shorter articles that I could collate into a book with some amplification. And I know the industry as well as anyone….so putting that into an easy-tounderstand book would be really valuable, I think. I just have to do it!
What advice would you give to aspiring leaders looking to make a meaningful impact in the retail industry?
This may sound trite, but my best advice is to stay human. Be accessible, be kind, but on the other hand, don’t take any nonsense from anyone. And…as a practical matter, spend some time working in every department you can. You will never understand someone else’s pain unless you’ve experienced it. So, work with the merchants, do a stint in distribution centers, and perhaps most importantly, work in a store a few times. I know it’s a pain to do that, but you learn things you otherwise never would. There just is no substitute for living what employees and managers live. You’re far less likely to recommend what I call “magic bullet technologies” if you understand the real issues these people face. It shocks me how many people don’t do that anymore.
