Thomas Obrien

About Thomas Obrien

I’m an educator, operator, leader, and builder working at the intersection of learning, leadership, and technology. Over the past 20+ years, I’ve worked across the full arc of education—from serving as a Peace Corps volunteer teaching business and marketing, to becoming a national award-winning math educator, to earning national recognitions as a high school principal, and now operating in edtech as Vice President of Success & Engagement. In my current role, I lead partnerships and program implementation across a wide range of contexts—from individual educators to large districts and national organizations. I design and scale programs, support leaders in improving academic outcomes, and build systems that help students succeed in math, college readiness, and beyond. My work is grounded in a simple belief: strong ideas only matter if they translate into real outcomes for students and educators. I’m most energized by building programs, developing people, and turning strategy into execution at scale. Alongside my professional work, I write about math, leadership, and the future of learning, including the growing role of AI in education. I’m particularly interested in how technology and AI can expand access, strengthen instruction, and help educators and organizations operate more effectively. I’m especially interested in building and leading programs, communities, and partnerships at the intersection of technology, AI, and learning—work that brings together strategy, execution, and meaningful impact. If you’re working on something in this space or thinking about what comes next for learning, I’d love to connect.

Experience

1. Vice President of Success & Engagement

   Winward Academy

   Jul 2022 — Present

   Lead customer success, partnerships, and implementation strategy for a global K–12 SaaS platform, driving adoption and outcomes across 2M+ monthly users- Drove 88% growth in lessons completed and 115% growth in time-on-platform year-over-year, significantly deepening engagement and accelerating learning at scale- Built and operationalized the full customer lifecycle, including onboarding, training, progress monitoring, and executive stakeholder communication- Drive platform adoption and engagement at scale, reaching 80K daily active users, through the design of training programs, facilitator guides, and implementation playbooks- Lead data-driven planning by analyzing usage metrics, engagement trends, and student performance data to set goals, remove barriers, and improve outcomes- Translate data insights into actionable plans for educators and system leaders, strengthening instructional practice and increasing student achievement- Serve as the bridge between educators and product/engineering teams—synthesizing user feedback into product requirements, supporting QA/UAT, and leading rollout strategy and training- Collaborate cross-functionally with product, sales, and marketing to improve user experience, align on growth strategy, and expand impact- Coach school and system leaders on effective implementation, ensuring sustained usage and measurable results across diverse contexts

Education

• University of New Mexico

  Master of Arts (MA), Secondary Education and Teaching

  2007 — 2009

• University of Oregon

  Bachelor of Science (BS), Economics and Math

  2003 — 2005

Skills

• Educational Consulting
• University Teaching
• Tutoring
• Classroom
• Nonprofits
• Teaching Adults
• Teaching
• Curriculum Development
• Public Speaking
• Educational Technology
• Community Outreach
• Professional Development Seminars
• Educational Leadership
• Teacher Training
• Staff Development
• Curriculum Design