Bridge Gap CFO – Business Consulting

Fractional CFO Transform and Optimize with AI

With over 20 years of experience in finance and operations, I founded Bridge Gap CFO.AI to help companies bridge the gaps their CFOs may encounter. I often say, “if you’re not working yourself out of a job, you’re not working in integrity,” and that philosophy—especially in the era of AI—guides how I serve every client. Finance leaders today must do more with less, and with the incredible advancements in technology, there are no excuses. Too many remain stuck in the past, hesitant to embrace change. I partner with you and your team to create, transform, and optimize with confidence.

I provide tailored consulting services designed to strengthen financial and operational performance, driving sustainable growth and efficiency. By leveraging AI, I reduce reliance on large data teams, enabling faster, smarter decision-making and greater agility. My team and I deliver fractional CFO leadership, strategic financial analysis, operational workflow optimization, and systems integration—giving your business a lasting competitive edge.

Having worked with organizations ranging from fast-paced startups to Fortune 500 companies, I bring a deep understanding of the unique challenges and opportunities that arise across every stage of growth.

~ Oscar Biondolillo, B.S. Finance, University of Illinois U-C

Services

CFO Leadership

We provide CFO leadership on a fractional basis, helping companies strengthen their financial strategy, streamline operations, and bridge gaps in performance.

FP&A

Our financial planning & analysis service offers insights into your financial health, helping you make informed decisions. We identify trends and provide actionable recommendations to boost profitability.

Workflow Optimization

We enhance your operational efficiency by analyzing current processes and implementing best practices. Our approach leads to reduced costs and improved productivity.

Systems Integration

Our systems integration service ensures your systems work together seamlessly, eliminating data silos and enhancing decision-making with real-time data access. By leveraging AI, we automate and streamline data flows, reducing the reliance on large data teams and enabling faster, more efficient insights across your organization.

Success Stories

Impactful Projects

Explore how we have transformed businesses through our tailored consulting solutions, ensuring efficiency and growth.

Finance & Operations Transformation During CFO Transition

During a CFO transition, I was brought in to stabilize finance operations and quickly expanded my role to cover FP&A, reporting, commission payouts, and product price increases. I optimized the FP&A infrastructure, automated GAAP-compliant reporting, and integrated NetSuite with Planful using AI and custom APIs—eliminating reliance on consultants or data teams. Partnering with executives, we created board decks, dashboards, and supported Series B raise. Created a 5-year forecast projecting ARR growth and company expansion. These initiatives streamlined processes, reduced reporting cycles by 50%, and positioned the company for scalable long-term success.

Strategic Finance & Operations Leadership Driving Scale and Growth

I joined during a finance executive search and expanded my role to cover finance, operations, fraud, and scalability initiatives. I oversaw payroll, AP/AR, and board reporting while automating reconciliations and integrating multiple systems with QuickBooks Online. I also implemented audit-compliant inventory controls across warehouses and platforms, supported crowdfunding raise, and helped build investor-grade reporting. Later, I transitioned to operations leadership, deploying automation and CRM tools that cut customer success headcount by 90% and helped position Mode as the fastest-growing company in America on Deloitte’s Fast 500 list.

Finance Liason for Divetstiture & FP&A Leadership

I supported the successful divestiture of a SaaS division, serving as the finance liaison with bankers, advisors, and legal teams to ensure smooth diligence and execution. I assumed global FP&A leadership, overseeing budgeting, forecasting, and reporting across multiple regions. I identified multimillion dollar misclassified marketing expenses and delivered several hundred thousands in AWS savings through contract renegotiations, directly improving EBITDA and cost efficiency. Additionally, I optimized their SAP/BPC consolidation tool to streamline forecasting and then partnered on ASC 606 compliance audit, achieving early audit approval and enhancing financial transparency.

Client Success Stories

Hear from our clients about how we transformed their operations and finances.

I had the privilege of working with Oscar at both CareerBuilder and Karbon, where he consistently made a significant impact. He blends strategic financial insight with operational execution, enabling leadership teams to make smarter decisions and scale effectively. Collaborative and solutions-oriented, Oscar elevates the finance function to drive growth and results. He also stands out as one of the most dedicated colleagues I’ve worked with. With an owner’s mindset, he brings care, accountability, and a relentless commitment to continuous improvement every single day. Any organization would be fortunate to partner with him.

I had the privilege of working with Oscar during his time at Karbon, where he was instrumental in strengthening our finance operations. He brought discipline to reporting while also helping identify opportunities for greater efficiency and scalability. Oscar has a unique ability to dive into the details without losing sight of the bigger picture, making him a trusted partner to both finance and executive leadership. Any company seeking to elevate their finance function would benefit from his expertise.

I had the privilege of working closely with Oscar at Mode Mobile, where he served as a pivotal leader in Finance and Operations. Oscar's forward-thinking approach truly set him apart as a tech-first innovator in the field. By leveraging AI tools to develop custom code for querying Zendesk and Ada, he revolutionized our customer success operations, enabling seamless data extraction and analysis that drove actionable insights. Drawing on his deep expertise in Financial Planning & Analysis (FP&A), Oscar orchestrated the integration of multiple disparate systems through citizen coding initiatives—empowering non-technical teams to build efficient workflows without relying on extensive IT resources. Under his visionary leadership, we transformed our Finance-led Customer Success model with business AI at its core, dramatically optimizing Ops headcount from over 40 to just 6, while maintaining—and even enhancing—service quality and scalability. Oscar's ability to blend financial acumen with cutting-edge technology not only delivered measurable efficiencies but also positioned our organization for sustainable growth. As he launches his own consulting firm, I have no doubt he'll bring the same transformative energy to his clients. Highly recommended for any team seeking a strategic, AI-driven Finance and Ops leader.