Oscar Carrasquillo
Co-Founder and Chief Executive Officer
Oscar Carrasquillo is an executive, entrepreneur, and business transformation leader with more than 30 years of experience across Fortune 100 companies, private equity-backed organizations, startups, and business turnarounds.
His work sits at the intersection of leadership, technology, operations, revenue growth, and practical AI execution. Throughout his career, he has helped organizations scale teams, expand into new markets, improve performance, and use emerging technology to strengthen human decision-making.
30+ years of leadership experience | $1B+ in sales impact | Teams scaled beyond 1,500 FTEs | Fortune 100, private equity, startup, and turnaround experience
Business Leadership Before AI Became a Trend
While many voices in AI have emerged recently, Oscar’s experience with technology, innovation, automation, and business transformation spans decades.
He has held senior leadership roles across revenue, operations, growth, customer experience, organizational development, and emerging technology. His career includes Fortune 100 environments, private equity-backed companies, startups, turnarounds, and ventures built from inception through expansion and exit.
That experience now shapes his leadership at The Gen AI, where he helps organizations move beyond fragmented AI experimentation and toward clear strategy, practical implementation, stronger business systems, and measurable outcomes.
A Career Built Around Growth, Scale, and Execution
Oscar has led organizations and teams through periods of rapid growth, operational complexity, market expansion, and transformation.
Scaling organizations to more than 1,500 full-time employees
Supporting more than $1 billion in sales
Achieving a historic 1,050% growth rate
Leading startup launches, expansions, turnarounds, and exits
Securing multimillion-dollar commercial relationships, including a $22 million partnership with Procter & Gamble
Expanding businesses into international markets
Improving customer experience, workforce productivity, and revenue performance
Applying technology and AI-supported insights to strengthen human decision-making
These results were not produced by technology alone.
They came from aligning strategy, people, operations, accountability, and execution around a clear commercial objective.That principle remains central to Oscar’s approach to AI today.
Leadership Across Enterprise, Growth, and Innovation
AT&T Mobility
Oscar co-founded, implemented, and managed AT&T Mobility’s first diversity-focused sales strategy within its virtual channels.
The initiative expanded access to new markets while connecting commercial growth with more inclusive market development.
Bank of America
At Bank of America, Oscar used emerging technology and operational improvements to achieve the highest customer experience ranking within his division, reaching 110% of target performance.
His work contributed to early automation and innovation initiatives designed to improve banking operations and customer service.
C Spire
Oscar implemented forward-looking strategies that strengthened customer experience, workforce efficiency, and sales performance, contributing to more than $400 million in annual revenue.
His work connected operational execution with technology, customer priorities, and the capabilities of frontline teams.
Vonage
At Vonage, Oscar led the company’s largest retail and SaaS expansion since its inception.
The initiative combined market development, sales execution, emerging technology, and tools designed to improve the effectiveness of customer-facing teams.
T-Mobile
Oscar’s leadership contributed to the highest gross profit performance in 10 of 11 consecutive quarters.
The result reflected a combination of operating discipline, strong sales fundamentals, innovative solutions, and the development of a high-performing team.
Cabeau
Oscar led a commercial transformation that produced 23% year-over-year growth in both 2018 and 2019 while supporting the company’s expansion into 118 countries.
The work involved strengthening strategy, sales execution, scalability, and international growth.
From Emerging Technology to Scalable Business Models
Oscar’s career has included both executive leadership and company building.
He has launched and exited multiple ventures, often focusing on opportunities where technology could improve scalability, workforce productivity, customer access, or operational efficiency.
During his career, Oscar also participated in early innovation efforts involving automated banking, intelligent recommendation capabilities, emerging interfaces, and technologies that anticipated later developments in digital assistants and AI-supported decision-making.
These experiences shaped his belief that innovation only matters when it can operate successfully inside a real business.Developing new market strategies
Creating revenue and operating models
Building and scaling teams
Leading business turnarounds
Expanding companies internationally
Integrating automation and analytics into sales and operations
Increasing valuation through stronger execution and growth
Taking emerging technologies from concept into practical use
AI Should Strengthen the Business, Not Complicate It
Oscar does not approach AI as a technology trend.
He approaches it as an executive and operating decision.
Organizations should not adopt AI simply because a new platform is available or because competitors are experimenting with it. They should adopt it where it can improve a defined business outcome and where leadership is prepared to support execution.
His perspective is built around several principles.
Business Outcomes Come First
AI initiatives should begin with a clear business objective, such as increasing revenue, improving productivity, strengthening customer experience, reducing operational friction, or improving decision-making.
Technology Must Work With People
AI can improve analysis, coordination, automation, and execution. It creates greater value when it strengthens the judgment and capabilities of employees rather than operating separately from them.
Strategy Must Be Executable
A strategy has limited value when it ends with recommendations. Leadership must also define ownership, priorities, governance, operating rules, implementation, and measurement.
Growth Requires More Than Tools
Sustainable growth comes from the combination of technology, human talent, operating discipline, leadership, and a commercial model that can scale.
AI Adoption Is a Leadership Responsibility
AI transformation cannot be delegated entirely to technology teams. Executives must decide where AI belongs, what risks are acceptable, how success will be measured, and how the organization will adapt.
Connecting Executive Strategy With Practical AI Execution
As Co-Founder and Chief Executive Officer of The Gen AI, Oscar leads the company’s strategic direction, client engagement, market positioning, and approach to business transformation.
Oscar is particularly involved in executive discovery, strategic advisory, business model evaluation, transformation planning, and long-term client partnerships.
His leadership helps ensure that The Gen AI does not operate like a conventional technology vendor.
Expanding Access to Practical AI
Oscar’s work is also shaped by a commitment to education, entrepreneurship, and broader access to emerging technology.
He has supported business communities, academic organizations, entrepreneurs, and leaders seeking to understand how AI can be used responsibly and practically.
Executive and business education
University and AI Lab collaborations
Conference speaking
Support for Hispanic business communities
Mentorship and entrepreneurship
Helping smaller organizations understand emerging technology
Creating practical pathways from AI awareness to business adoption
For Oscar, broader access to AI should not mean encouraging organizations to adopt every new tool.
It means giving leaders the knowledge and structure required to make informed decisions.Experience Shaped by Resilience, Opportunity, and Responsibility
Oscar’s personal journey began in Puerto Rico and continued in East Los Angeles, where his early experiences shaped his perspective on resilience, opportunity, leadership, and inclusion.
Those experiences influenced the way he approaches business today.
He understands that talent and potential are widely distributed, while access to technology, networks, capital, and opportunity often is not.
Throughout his career, Oscar has worked to build organizations, teams, and commercial strategies that create measurable performance while expanding the ability of people to contribute and succeed.
Performance at a Glance
Executive, technology, growth, and operating leadership
Teams scaled and led
Sales impact across organizations and ventures
Historic growth achieved
Annual revenue contribution at C Spire
Commercial partnership secured with Procter & Gamble
International expansion supported at Cabeau
Go-to-market execution through SalesMakers
Launched, scaled, and exited
Discuss Your Organization’s AI Priorities With Oscar
Organizations do not need another conversation about AI possibilities.
They need clarity about where AI belongs, what should be prioritized, and how strategy can be carried into execution.
Meet with Oscar and The Gen AI team to discuss your current initiatives, growth objectives, operating challenges, and the role AI could play in strengthening the business.