Debleena Roy: Guiding Wall Street Leaders with Purpose

As the Founder of the coaching firm Choice Over Chance and Co-Founder and CFO of Jacktrade, Debleena “ Leena ” Roy exemplifies versatile leadership. With her personalized approach to human transformation through Choice Over Chance and mission to support small business growth through Jacktrade, Debleena leverages over 15 years of risk management and coaching to steer highly regulated businesses and motivated individuals to strive for success and do it safely.    

Debleena holds over a decade of finance expertise, including senior management roles at Barclays and Robinhood, where she ran the regulatory reporting team, and built risk frameworks for traditional and digital assets. Her blend of financial acumen and genuine care for human achievement, position Debleena as a leader driving change through both individual and organizational transformation.   

Transitions Shaping Perspectives

Debleena’s life has been defined by transitions that have shaped her into the inspirational leader she is today. Born in Raleigh, her family moved back to Kolkata, India, when she was four years old. This 14-year period in India during Debleena’s formative years cultivated deep bonds with family and friends and profoundly impacted her worldview. At 18, Debleena returned to the U.S. to attend Boston University. This transition was difficult, as she left behind the city and the people she loved in India. However, through perseverance and an open heart, Debleena built strong friendships and thrived professionally in finance in New York City.   

Debleena’s personal transitions taught her resilience in the face of change and the importance of community, family, and embracing new cultures and experiences. She learned, “Home is not one place, but the feeling I get when I surround myself with the people and things (and food!) that fill me meaningfully.” Her personal growth mindset also propels her drive for self-improvement. Debleena shares, “I spent years in New York learning Vedanta, an Indian philosophy rooted in learning about my ‘self’ and to focus inwards for growth and change. This is the foundation of my coaching practice.”   

A Standout Leader Across Finance and Coaching

Holding a Bachelor of Science in Business Administration (BSBA) with a concentration in Finance and a minor in International Relations from Boston University, Debleena began her career in finance, holding risk management and regulatory compliance roles at prominent institutions like Barclays, Fidelity Investments, and FINRA. She obtained the esteemed Chartered Financial Analyst (CFA) designation, leveraging her analytical capabilities.   

However, Debleena has never been “one thing or one person,” with her Gemini nature drawing her to variety. She always felt passionate about helping people, in addition to finance. In her 30s, a friend introduced Debleena to Momentum Education’s leadership program. This transformative experience opened her eyes to the power of coaching. She subsequently volunteered as a coach for Momentum and other youth organizations, before pursuing professional certification from the Institute for Professional Excellence in Coaching (IPEC).    

Debleena has since built impressive experience across both domains. As Head of Risk and Regulatory Reporting at companies like Robinhood and Barclays, she’s established frameworks to identify, monitor, and report on critical risks and transform regulatory reporting processes. At Fidelity Investments, she rose to Director, with oversight across the firm’s portfolio of retail and correspondent market risk exposure.    

Debleena’s blend of technical excellence and passion for transformational personal impact equip her to drive success, whether in finance or coaching. Her multifaceted talents allow Debleena to thrive across diverse domains.   

Empowering Leaders Through Personalized Coaching

After obtaining over 650 hours of coaching and guiding over 125 clients, Debleena founded her coaching company, Choice Over Chance, in 2013. She noticed a gap in the market for personalized one-on-one coaching. Debleena explains, “At the time I started my coaching practice, I saw a big focus on group coaching and workshops and the gap I wanted to address was the need for customized, personalized attention to drive action.”   

The name Choice Over Chance encapsulates Debleena’s coaching methodology. She focuses on moving clients from a “can’t do” mindset to a “can do” mindset. Her energetic approach involves understanding a client’s story and limiting beliefs and then working together to shift perspective and identify attainable goals and plans. The emphasis is on making intentional choices, rather than leaving life up to chance, and clients feel empowered by this method.   

Debleena works extensively with mid-level professionals to help uncover their inner leader. She shares, “It is easy to feel motivated during a workshop. What is tough is understanding how to apply your learning to navigate through your unique situation and changing your narrative at work.” Debleena provides clients with personalized support so they can continue making empowered choices.   

The Future of Small Business Growth

Beyond her work with Choice Over Chance, Debleena co-founded Jacktrade in 2018 with Dev Cham. Serving as the Chief Financial Officer, Debleena oversees the company’s financial operations, planning, and budgeting, leveraging her vast experience in finance to guide the startup’s strategic direction. Jacktrade is a comprehensive customer management platform designed for non-store retailers, providing an all-encompassing business system that supports small businesses in achieving success by enabling marketing, sales, service, and operations teams to collaborate seamlessly and remove friction in the buyer’s journey, ultimately enhancing earnings, freedom, and growth.   

With a mission to grant small businesses access to quick, easy, innovative, and complete technology solutions, Jacktrade is dedicated to building a successful business ecosystem that offers entrepreneurs freedom and peace of mind. The vision is to level the playing field, allowing small businesses to not just survive but flourish in a competitive market.   

Empowering Others Through Her Journey

Debleena’s global upbringing gifted her the motto she now passes on to clients: bloom wherever life plants you. Through every transition, she reinvents herself without losing her essence. Like a tree growing upwards in pursuit of light, Debleena models the power of choice and resilience no matter the disruption. She guides clients to access their inner wisdom and make decisions that align with their truth.   

Above all, Debleena’s journey has illuminated that one’s purpose and community can thrive anywhere. Human bonds built on trust and understanding transcend all barriers. Her coaching empowers people to let go of what no longer serves them and reinvent fearlessly.   

Reflecting on her transition from a scared 18-year-old with faded red suitcases to a sage coach, Debleena’s narrative is a reminder of the unforeseeable richness life offers to those brave enough to embrace its uncertainties. Her evolution from confronting change with courage to transforming serendipitous encounters into a meaningful life illustrates the essence of living by design, not by chance.   

Moreover, Debleena’s seamless integration of her financial and strategic expertise with her coaching practice showcases her unique ability to bridge disparate worlds. Managing teams in the finance sector while nurturing personal growth through coaching, she brings out the best in people, highlighting her belief in the harmony between analytical rigor and transformational development.   

Debleena Roy ’s multifaceted career is a guiding light for those seeking to navigate life’s transitions with grace. Her resilience, openness to new experiences, and dedication to lifelong learning serve as a powerful model for transforming lives. Whether through finance or coaching, Debleena uplifts others, inspiring them to make empowered choices and forge a path filled with purpose and connection.