Jennifer D. D.

I help CEOs, founders, and executive teams develop AI strategies, make sound technology investments, and architect AI solutions that deliver measurable business value. I combine executive AI leadership, enterprise architecture, and hands-on technical expertise. I've served as CTO for three startups, held senior roles at IBM Watson Health, Accenture, and Domino Data Lab, and currently facilitate AI Strategy executive education at MIT Sloan (via 2U), working with more than 2,000 executives and business leaders. PROVEN EXPERIENCE - 200+ Upwork projects | $800K+ earned | 4.9/5 client rating - Three startup CTO engagements - $5M+ in annual client savings from a computer vision engagement - 10+ years of enterprise AI/ML experience - Executive AI education through 2U at MIT Sloan; previously taught deep learning through Columbia University AI STRATEGY & EXECUTIVE ADVISORY I work with CEOs, founders, and leadership teams to translate AI opportunities into practical business strategies. - Enterprise AI strategy and transformation roadmaps - Generative AI adoption and implementation planning - AI use-case assessment, prioritization, and ROI - AI business cases and investment decisions - Build-vs-buy analysis and vendor evaluation - AI governance, security, and risk management - Executive AI coaching, education, and advisory - AI product strategy and technology due diligence My approach starts with business objectives, not tools. I help organizations determine where AI creates value, what investments make sense, and how to execute effectively. FRACTIONAL CTO & TECHNOLOGY LEADERSHIP As a three-time startup CTO, I understand the intersection of technology, product strategy, budgets, teams, and business growth. - Fractional CTO and fractional AI leadership - Technology strategy and product roadmaps - AI architecture and engineering oversight - Technical audits and due diligence - Startup MVP planning and product development - Technical team and vendor evaluation - Scalability, reliability, and cost optimization - Translating executive priorities into technical requirements I provide experienced technical leadership without the commitment of a full-time executive. AI/LLM ARCHITECTURE & ENGINEERING Unlike consultants who focus solely on strategy, I bring the technical depth to design, evaluate, and guide implementation of sophisticated AI systems. - Generative AI and large language models (LLMs) - AI agents, agentic AI, and workflow orchestration - Retrieval-Augmented Generation (RAG) and semantic search - Enterprise knowledge systems and document intelligence - Natural language processing (NLP) and machine learning - LLM evaluation, validation, and reliability - AI security, privacy, and governance - Python, APIs, data pipelines, and distributed computing - MLOps, LLMOps, and production AI architecture - AI platform audits and architecture modernization SELECTED RESULTS $5M+ Annual Savings: Diagnosed a critical technical issue in a computer vision engagement, leading to more than $5 million in annual client savings. Startup CTO Leadership: Served as CTO across three startup engagements, advising founders on technology strategy, architecture, product development, and technical execution. Enterprise LLM Architecture: Designed a multi-stage LLM solution integrating evidence extraction, semantic clustering, ranking, validation, source tracking, and API delivery. AI Advisory & Technical Audits: Delivered AI strategy consultations, platform assessments, private-SLM, LLM and frontier models advisory, conversational AI architecture, and technical due diligence. Executive AI Education: Facilitate MIT Sloan's AI Strategy program for business leaders and previously taught deep learning and neural networks through Columbia University. WHY CLIENTS WORK WITH ME My Upwork feedback consistently highlights quality, clear communication, collaboration, professionalism, and solution-oriented thinking. I bridge the gap between executive strategy and technical implementation. Sometimes the right solution is an enterprise AI platform. Sometimes it's a targeted automation, an architecture improvement, or a decision not to use AI at all. Whether you're developing an AI strategy, seeking fractional CTO leadership, evaluating an AI investment, or building a complex LLM solution, I bring the strategic judgment and technical expertise to help you move forward. Let's discuss your AI strategy, technology challenges, or next initiative.