RAPHAEL BENNETT

The rare blend of a Chief Technology Officer and a Chief Financial Officer

I operate at the critical intersection of technology and finance, delivering the expertise of a CTO with the risk-mitigation focus of a CFO. I structure capital for mission-critical sectors, including securing essential funding for National Security and Defense projects that support an America First priority. Simultaneously, I structure off-market investments into Energy, Critical Infrastructure, and Opportunity Zones to deliver significant tax-advantaged returns for the REV Global Community, Partners, and High Net Worth Investors. I also lead AI-enhanced due diligence efforts on both buy and sell sides, ensuring every acquisition or exit is financially sound, properly priced, and technically optimized.

Professional experience

A wide variety of skills derived from operating experience across an array of technical and capital projects

My foundation is in technology, beginning my career as a Software Engineer and consistently serving as a Chief Technologist for every venture. While I continue to enjoy the process of building and scaling businesses as a 2x exited founder and operator—focusing on sound architecture, delightful user experiences, and rigorous product-market fit—my practice has evolved.

Today, I leverage this deep technical knowledge as a Financial Engineer and Capital Strategist, specializing in advanced M&A diligence, high-impact financial migrations, and structuring tax-advantaged alternative investments for high-net-worth capital.

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AI-First Strategic Diligence

I lead due diligence with an AI-First methodology, integrating advanced machine learning and proprietary tools directly into the M&A process. My CTO/CFO dual-lens ensures AI is deployed not just for data collection, but to generate actionable insights that critically impact deal terms—from preemptive defect discovery on the sell-side to negotiating a compressed acquisition price on the buy-side.

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Capital Formation & Financial Engineering

I specialize in structuring and deploying capital for high-net-worth investors and family offices by identifying off-market alternative investments that deliver significant tax efficiency and alpha. This expertise facilitates income relief through investments in Energy, Critical Infrastructure, and Legacy Oil and Gas to secure tax-advantaged opportunities that reduce earned income liability. I also structure investments into targeted Opportunity Zones (primarily manufacturing and services) for effective Capital Gains deferral and potential elimination.

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Financial Engineering

Leveraging a background in software development and technical architecture, I specialize in driving complex, high-stakes financial transformations and migrations—ensuring seamless, secure, and compliant transitions across treasury, accounting, and compliance systems. Crucially, I integrate AI enablement into legacy and modern financial stacks, transforming data analysis, risk modeling, and reporting from a cost center into a core competitive advantage. This expertise is critical for high-growth firms and institutions undergoing massive operational change.

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VC Tech wind downs, & Tech Asset salvage

In most cases a new venture will fail, but that doesn’t mean that it didn’t contain value. Often times VC operators (GPs) will commission me and my team to evaluate the tech, value the tech, and secure a new owner through a salvage asset sale; often through bankruptcy.

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founder coaching & Governance

As founder I know how important it is to stay ahead of corporate governance. As founders architect their products, build their teams, they often overlook the compliance and governance that outlines who gets what, and how that changes based on what happens in the company.

Preferred Tooling

Engineering & Architecting

Clojure (reframe/reagent), Kafka, nomad, AWS, Terraform, confluent, expo, Docker, kubernetes, event modelling, figma, & Vault.

Remote Engineering

ActiveCollab, Hubstaff, Upwork, Fivver, & Deel

Sales & Marketing Automation

Hubspot, Apollo, Intercom, Instagram, facebook, youtube, Linkedin, & Tiktok,