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 off-market investments into Energy, Critical Infrastructure, and Opportunity Zones to deliver significant tax-advantaged returns for HNW investors. Furthermore, I lead AI-enhanced due diligence efforts on both buy and sell sides, ensuring every acquisition or exit is financially sound and technically optimized.
Professional experience
A wide variety of skills derived from operating experience across an array of technical projects
Beginning my career as a software engineer, I have always led as a Chief Technologist in every business I have been a part of.
In my time as a founder, entrepreneur, and operator, I have enjoyed the experience of building businesses and launching products from scratch. I enjoy the process of discovering cumbersome challenges, building products that are a delight to use by incorporating well designed user experiences, sound technology, and scaled with a well developed product market fit strategy.
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.
Remote Engineering team development
Team development decisions can make or break your project. I’m a big believer in building a “remote first” culture. It opens the talent pool, reduces cost, and can be very rewarding for all. However, it can be very frustrating when improperly managed.
sales and marketing automation
There isn’t anything more exciting than achieving product market fit, yet many operators never fully scale to their potential without a strong automation plan. I find the technical side of funnel engineering exciting, and I love seeing a team’s excitement rally around growth velocity.
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.
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,