Jacqueline Ann DeStefano-Tangorra, CPA started her career as a financial auditor and technology consultant at PwC. After seven years, Jacqueline realized that leading a company is what she envisioned for herself and resigned to establish Omni Business Intelligence Solutions (OBIS), a boutique consulting firm in 2021. OBIS offerings include AI-driven, data-centric solutions provided to over 130 clients across 25+ industries worldwide, many of which she found on the work marketplace, Upwork. Her innovative use of generative AI, notably OpenAI’s ChatGPT, has accelerated the growth of OBIS, earning OBIS a feature in Business Insider and Yahoo Finance.

What does “entrepreneurship” mean to you?
Jacqueline Ann DeStefano-Tangorra: To me, “entrepreneurship” signifies the audacity to dream, innovate, and create value. It’s the embodiment of courage, resilience, and continuous learning that translates into the generation of solutions that meet specific needs. Entrepreneurship is a dynamic process that demands adaptability and an intuitive understanding of market needs. For example, I continuously expand my skill set to keep pace with emerging trends. As an entrepreneur, it’s crucial to remain agile in the evolving landscape of technology. Recognizing the impact of AI in the business landscape, I reinvested in my education and learned the applications of Generative AI, reskilling that allowed me to grow and scale my business effectively.

Entrepreneurship, in essence, is a relentless pursuit of innovation, adaptability, and relevance. It’s about being a trailblazer, anticipating market trends, and leveraging your skills and knowledge to deliver timely and impactful solutions.

What do you wish you knew when you started? Is there anything you would do differently?
JD-T: Looking back, I wish I had known the importance of patience and pacing in the journey of entrepreneurship. I recall the immense pressure I placed on myself when I departed PwC to pioneer my own venture. While a structured plan is certainly crucial, it’s equally vital to pause and appreciate the incremental milestones and achievements that contribute to long-term success. I now understand that a significant venture such as this doesn’t come to fruition overnight—Rome wasn’t built in a day.

If I had the chance to do things differently, I would have sought out resources, mentorship, and guidance earlier in my journey. Initially, there were areas I was unfamiliar with, and I underestimated the power of asking for help and learning from those who had walked the path before me. Additionally, I now understand that making a financial investment in the business is not just about having ‘skin in the game.’ It’s an essential component of growth and scaling.

What does “success” look like for you? We’d love to hear your biggest, boldest dream. What do you think will help you achieve it?
JD-T: For me, “success” is derived from the “aha” moments I share with my clients. While financial growth in the company is undoubtedly an essential objective, the satisfaction derived from innovating a unique solution or helping a client overcome a complex challenge is unparalleled. I believe true success lies in the value you provide and the difference you make. And I have found that if you’re focused on the customer experience, not just the money – that is what makes a successful business. In turn, the finances will follow.

I want to see OBIS grow into an enterprise-level business intelligence firm that empowers businesses globally to operate more effectively and efficiently by harnessing the immense power of data intelligence. I also want to continually grow my network and build new long-term relationships with customers, whether it’s finding new clients on Upwork or through connections I make each and every day. I dream of unlocking untapped potential within companies by transforming the way they use data, leading to more informed decisions, increased productivity, and enhanced business performance.
Achieving this ambitious vision, in my belief, requires a roadmap of three combined elements – faith, self-belief, and a relentless commitment to client satisfaction. I firmly believe that if this dream aligns with God’s will, nothing can hinder its realization.

What is your superpower as an entrepreneur? What is your proudest and darkest moment so far? Share a key high and a key low from your journey if you can.
JD-T: My superpower as an entrepreneur lies in my ability to serve as a bridge in communicating complex topics. I have the knack for taking intricate, challenging concepts and breaking them down into understandable language for my clients. It’s not just about effective communication, but also the ability to gauge the audience and adapt my delivery accordingly. This skill is particularly crucial in my field, where I often have to explain advanced technological concepts in a manner that is easily digestible and applicable to my clients.

One of the proudest moments in my entrepreneurial journey was when my company, OBIS, was featured in prominent publications such as Business Insider and Yahoo Finance. It validated my vision and the tireless efforts of my team, reflecting the impact we were making in the industry.

On the other hand, a dark moment occurred when I initially left my stable job at PwC to venture into entrepreneurship. The transition was fraught with uncertainties, doubts, and fears about the future. It was a test of my courage and determination, a low point that nevertheless served as a catalyst for the growth and success that followed.

What are your personal driving principles, your top values? How have those personal principles and values shaped your company’s values and principles?
JD-T: Two strong personal principles I have is the value of my faith being the cornerstone of my life and being receptive to mentorship and feedback. These core values are important because when you are building a business, and serving clients with different business structures, personalities, and teams, many core values can often be tested, but pride should never be a barrier to growth and understanding. These principles translate to an organizational culture that values openness, constructive feedback, and continual learning, as well as a culture that has an ethical standard that we adhere to.

Do you have a mentor? Tell us about what makes them valuable to you and your business.
JD-T: I still have several mentors from my time when I worked at PwC who supported me when I took the courageous leap to leave the corporate world. They became integral in helping me identify business groups and opportunities when I was just starting my business.

On a personal level, I look to my parents for guidance since they know me the best. My mom has been such an excellent resource of wisdom and guidance as it relates to helping me properly manage the finances of the business infrastructure early on. My dad finds unique opportunities and always has his ears and mind open for opportunities that I could benefit from being a part of or pursuing. Both of them together have had a tremendous influence and impact on my entrepreneurial journey and I am so grateful to both of them, as they recognize how hard it can be to build a business from scratch.

Many entrepreneurs continue to perfect their daily routines to support their work and greater vision; would you mind sharing your morning routine or a regular ritual that grounds your work each day?
JD-T: My daily routine is an integral part of maintaining balance and focus in my work. I start my day early, waking up at 5:15 AM to hit the gym with my husband. This early morning exercise not only invigorates my body but also helps clear my mind and prepares me for the day ahead.

Post-workout, I take some time to walk my dog, embracing the peace of the early hours. This quiet time in the morning is set aside for non-work-related activities. Whether it’s listening to my favorite music or praying, these moments of calm provide a much-needed respite and help center me for the day ahead. Then I set my goals for the week, respond to emails, and plan my agenda. This uninterrupted time allows me to get ahead, enabling me to respond to the day’s challenges with preparedness and a clear vision.

Do you have a favorite quote, mantra, or words of wisdom to get through the tough days?
JD-T: “She is clothed with strength and dignity, and she laughs without fear of the future” – Proverbs 31

What is a problem that keeps you up at night?
JD-T: Generative AI. The benefits of AI excite me, I see it as a force multiplier for my business. There are several processes that can be automated, accelerated, and augmented. As a business owner, there are various use cases of AI that have helped me save money and time, and also win new contracts. My fear is that if we don’t find a way to centralize these GenAI solutions somehow, we’re all going to be tied up in subscription madness. I know many people are concerned with AI replacing jobs, but a bot is not enough to provide high-quality service to clients. Relationships and creativity will remain crucial and will never go away. But figuring out what humanity’s role is going to be 5-10 years from now and how a business like OBIS will adapt throughout these fast-paced technological changes, does make me wonder some days, like many of us.

What advice do you have for fellow (and aspiring) entrepreneurs building and leading teams?
JD-T: As an entrepreneur, you have to be quick on your feet. I’ve pivoted twice in my career. My first pivot was getting my CPA license and then pursuing a career in technology after five years of doing financial accounting. I saw the value in getting a tech education because I recognized that. My second pivot occurred after I started my business, learning Generative AI, bringing it in as a strategic offering after upskilling tremendously (Open AI APIs, ChatGPT use cases, prompt engineering, etc). And platforms like Upwork have enabled me to have the confidence and support needed to pivot successfully because I was able to win work in the marketplace that allowed me to grow and develop skills relevant to the career path I wanted to pursue. Upwork allowed me to start building my brand and client roster.

I encourage aspiring entrepreneurs to see the current world they are in and envision the world they want to live in. In between those two worlds, you need to identify what your transferable skills are and how you can leverage those to make a subtle leap. When I was an accountant, I mastered the art of data cleanup. And in business intelligence, data quality is an extremely important part of building solutions for clients. So, this was a skill I developed in another world that benefited me in the world I chose to pursue my career as an entrepreneur.

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