Jason Callina
Founder & CTO, Mastermind Adventures
jcallina@mastermindadventures.com | 508-916-2187
Massachusetts & New Hampshire
Executive Snapshot
Founder/CTO driving innovation in AI-powered, scenario-based education and workforce training. I excel at turning concepts into market-ready prototypes and MVPs, building lean engineering teams, and embedding them within organizations to improve communication and accelerate results. Currently leading Mastermind Adventures, delivering immersive learning experiences for global audiences, while open to fractional CTO and consulting roles where speed, clarity, and results matter most.
Top Wins
• Founded Mastermind Adventures, pioneering AI-driven, story-driven training that blends immersive narratives with interactive technology, engaging thousands in large-scale educational, workforce, and therapeutic programs.
• Blended game mechanics, behavioral insights, and data analysis to develop original, industry-spanning products — from early narrative game systems to social intelligence tools for hospitality and AI-enabled learning platforms.
• Drove measurable savings and accelerated delivery by adopting open-source solutions, optimizing infrastructure for scale, and transforming engineering from a cost center into a trusted strategic partner.
Mastermind Adventures — Founder & CTO
2016–Present
Developing AI-powered learning experiences that merge immersive storytelling with interactive technology for education, workforce training, and personal development.
• Founded and grew an AI-driven learning company delivering interactive, story-based training for education, workforce development, and personal growth.
• Conceived, built, and launched Bubot, an AI-powered platform running live training scenarios for enterprise workforce programs, including pilots with a top-ten national private company and deployments reaching hundreds of participants.
• Scaled product development using a lean, high-velocity stack (Rails, React, OpenAI, AWS) while tailoring engineering capabilities per client to maximize ROI and accelerate adoption.
Fractional CTO & Senior Technical Leadership
Offer CTO-level strategy, product innovation, and engineering leadership built on 20+ years as a founder, senior engineer, and technical lead. Experienced in guiding products from concept to scale, aligning technology with business goals, and leading teams to deliver measurable results.
Technical Strategy & Architecture – Translate product vision into scalable technical roadmaps, select lean, high-impact tech stacks, and architect systems for long-term adaptability and performance.
Product Innovation – Integrate AI, automation, and emerging technologies to create market-ready products, including Bubot, an AI-driven learning platform in active use by enterprise clients.
Engineering Leadership – Build and mentor nimble engineering teams, foster collaboration across departments, and ensure engineering is viewed as a strategic partner rather than a cost center.
Operational Efficiency – Implement open-source solutions, infrastructure optimizations, and streamlined processes that reduce costs, accelerate delivery, and improve reliability.
Cross-Industry Expertise – Proven impact in education, healthcare, gaming, hospitality, and research, applying data-driven insights and behavioral design to deliver engaging, outcome-focused solutions.
Core Technologies and Platforms
Cloud & DevOps: AWS (Lambda, DynamoDB, EC2, S3, Polly), Terraform, Serverless Framework, CI/CD
Back-end: Ruby on Rails, Node.js, Express, REST APIs, GraphQL
Front-end: React, TypeScript, JavaScript, MUI
Data & Storage: Postgres, Redis, MongoDB, MySQL
AI & Emerging Tech: OpenAI APIs, ChatGPT integration, procedural content systems
Additional Expertise: Advanced image processing, payment processing (Stripe, PayPal), social media data analysis
Previous Experience
Pair Team — Staff Software Engineer
2024
Key member of the core team designing and implementing the new Care Team experience — a summary dashboard surfacing critical patient information, family relationships, and related needs. This tool enabled care teams to address individual and family requirements holistically, supporting long-term success for patients with complex medical and social challenges.
Woebot Health — Senior Software Engineer
2022–2023
Built features for enterprise healthcare partners and orchestrated integrations between proprietary systems and our platform. Ensured compliance with strict security and performance requirements while streamlining partner onboarding. Enhanced developer efficiency by refining workflows and automating processes for code quality, data integrity, and security, enabling faster, more reliable delivery at scale.
SquadLocker — Lead Software Engineer
2020–2022
Spearheaded new e-commerce capabilities, including Uniform Collections for coordinated product purchases and advanced image processing tools for previewing multiple logos on apparel. Achieved significant cost savings and improved stability by optimizing database connections and eliminating critical bugs that had caused costly downtime.
CoachUp — Senior Software Engineer
2017–2020
Maintained and expanded core features for the flagship web application serving over half a million registered users and 100,000+ coaches. Collaborated with stakeholders to translate client needs into tailored solutions, and upgraded analytics and financial reporting through auditing and optimization. These efforts accelerated delivery of new capabilities, improved operational accuracy, and boosted engagement and retention.
TripCraft — Senior Software Engineer
2012–2017
Engineered advanced social scoring libraries that identified and valued hotel visitors based on their social media presence, enabling targeted marketing and loyalty programs. Led the technical design and integration of legacy SOAP reservation APIs with modern frameworks, streamlining booking processes and enhancing scalability.
DisruptorBeam — Lead Software Engineer
2010–2011
Provided technical leadership for high-profile projects, including core programming for 50 Cent's Blackjack on The Game Show Network. Created procedural content generation libraries for Gods of Rock and contributed early gameplay concepts for Game of Thrones Ascent, blending creative design with robust engineering.
Berkman Klein Center for Internet & Society, Harvard University — Senior Technologist
2006–2010
Partnered with academics and researchers to translate cutting-edge research into production-ready software. Designed tools for cybersecurity, malware analysis, sociopolitical data research, and educational technology, with projects backed by organizations such as the U.S. State Department and Google. Pioneered research automation systems and leveraged crowd-sourced data to advance scholarly work, enabling faster insights and broader participation.