Andrew Ressler

Chief Technology Officer & Chief AI Officer at Alumni Ventures

North Reading, Massachusetts, United States

About Andrew Ressler

Andrew Ressler is Chief Technology Officer & Chief AI Officer at Alumni Ventures. Location: North Reading, Massachusetts, United States.

Chief AI Officer, CTO, and technology executive with 25+ years of experience building and scaling AI, machine learning, analytics, search, recommendation, and large-scale software platforms that drive measurable business growth. Currently leading enterprise AI strategy, architecture, governance, and hands-on implementation at Alumni Ventures. Responsible for production AI systems spanning proprietary investment intelligence, internal AI copilots, customer-facing AI products, predictive machine learning models, RAG architectures, agentic workflows, and secure AI access to proprietary enterprise data. My focus is helping organizations move AI from experimentation to production. This includes defining AI strategy, establishing governance and evaluation frameworks, building scalable AI and data platforms, and creating the organizational processes required to deploy AI responsibly and effectively across business functions. Prior experience spans venture capital, gaming, advertising, search, digital marketing, and consumer internet businesses. Throughout my career, I have combined executive leadership with deep technical involvement, leading teams while remaining actively engaged in architecture, product strategy, and implementation. Selected results: • Lead enterprise AI transformation initiatives across investment, sales, operations, and customer-facing functions at Alumni Ventures • Drove a major strategic shift in fund positioning and sales strategy through analytics and customer insights • Increased revenue per user at GSN Casino by 50% in six months through analytics, personalization, and optimization • Increased advertising revenue more than 20X at Helium.com through analytics and monetization initiatives • Led search, advertising, recommendation, and analytics platform initiatives across multiple consumer technology businesses Core expertise: Enterprise AI Strategy • AI Transformation • AI Governance • Enterprise AI Architecture • Generative AI • RAG & Agentic Systems • Machine Learning (ML) • Recommendation Systems • Product Strategy • Data Analytics • Monetization • Cloud Architecture • Executive Leadership

Skills

  • Enterprise AI Architecture
  • Retrieval-Augmented Generation (RAG)
  • Model Context Protocol (MCP)

Additional experience

  • SVP, Data Analytics

    Alumni Ventures

    January 2022 – August 2022

Education

  • M.S., Massachusetts Institute of Technology
  • PhD, Massachusetts Institute of Technology