Matthew Occhi

About Matthew Occhi

I lead go to market at Rolai, helping colleges and universities adopt AI in a way that is governed, measurable, and built for real campus work. We bring AI into one secure environment that connects to your campus systems and institutional knowledge, so teams can use it where work actually happens.Many institutions are navigating AI tool sprawl, inconsistent usage, and unclear ROI. Rolai makes adoption practical by pairing strong controls and permissions with role-based agents and workflows, plus reporting that helps leaders understand usage and outcomes.What I focus on:• Identifying the highest value use cases and turning them into pilots that prove impact quickly• Enabling agents and workflows that support real work, not just chat• Supporting adoption through AI Literacy and Fluency so teams build confidence and consistency• Partnering with IT and functional leaders to align AI with institutional risk, policy, and prioritiesIf you are exploring governed AI in higher education, actively evaluating solutions, or simply curious and want to compare notes, I would love to connect.

Experience

1. Gtm Lead

   Rolai

   Nov 2023 — Present · Boston, MA, US

   Lead go-to-market across enterprise and departmental motions, starting with governance to de-risk adoption, then expanding through high-impact use casesPartner with campus leaders to deploy a unified AI platform with multi-model access, agents, workflow automation, governance, and analyticsDrive pilots that connect AI to institutional knowledge and systemsSupport departments across Teaching and Learning, Enrollment, Student Success, Grants, and admin operations with measurable operational outcomes

Education

• Roger Williams University

  Bachelor's degree