Who you are

• Has 10+ years in software engineering, including 3+ years at Staff/Principal level (or equivalent technical leadership)
• Possesses a proven track record of delivering large-scale, event-driven systems and rapid prototypes
• Has hands-on coding expertise in Node.js with TypeScript, while also influencing at a strategic level
• Has experience building and launching AI-powered products with LLMs (e.g., RAG, fine-tuning, vector DBs, embeddings, AI-assisted coding tools)
• Has strong architectural leadership — designing complex, distributed systems, delegating effectively, and mentoring senior engineers
• Holds the ability to translate business goals into actionable, scalable, and maintainable technical roadmaps
• Has high customer/stakeholder empathy with a focus on end-user value
• Is an exceptional communicator who is confident in engaging executives and cross-functional leaders
• Ruby on Rails
• ML model training or fine-tuning
• SaaS/cloud-native architecture experience
• Familiarity with modern web frameworks beyond Node/TS
• Competitive product/technical research
• AI/ML compliance and governance frameworks
• Public technical evangelism, community contributions, or thought leadership

What the job involves

• Are you ready to shape the future of education by leading AI strategy at a mission-driven company? We’re looking for a Principal AI Engineer to join us. You won’t just be told what to build, you’ll define it. You’ll lead our flagship AI Teaching Assistant, transforming how people teach and learn online. With the freedom to explore bold ideas, adapt innovations, and influence our AI strategy, you’ll make a visible impact in a company small enough for agility and established enough to back big ideas
• Transformative project – Redefine online learning with our AI Teaching Assistant
• Frontline innovation – Drive strategy and bring fresh ideas to life
• High impact – Collaborate directly with senior leadership
• Growth – Shape the culture and future of our AI team
• Your goal will be to own a strategic area within R&D, ensuring business success through impactful technical decisions — from identifying and prototyping AI initiatives to delivering reliable, scalable production systems. Here’s how you’ll accomplish this:
• Lead AI architecture & vision – Define technical direction, guide Staff Engineers, and ensure scalable, high-quality solutions
• Shape the roadmap – Partner with R&D leadership to turn strategic AI opportunities into actionable engineering plans
• Be Thinkific’s AI authority – Advise senior leadership, showcase AI capabilities, and share insights internally and externally
• Grow the AI team – Mentor engineers, support hiring, and foster technical excellence
• Research & innovate – Explore emerging AI/ML tech, assess competitors, and translate findings into product opportunities
• Ensure operational excellence – Own costs, scalability, and reliability metrics for your AI domains
• Engage with the community – Contribute to blogs, conferences, and industry discussions while staying ahead of the curve

Benefits

• Open vacation policy: We're big proponents of sand, sun, and taking time to recharge. As long as you're getting your work done and keeping your team supported, take vacation when you need it. We encourage Thinkers to take at least 4 weeks vacation each year
• Flexible work environments: Whether you’re working from Thinkific HQ or working from home, set your own hours to find a rhythm that works for you and your team. Finding the time for workouts, laundry, daycare dropoffs, or appointments is easier than ever.
• Learning opportunities and personal development: Interested in a course, conference, or career coaching? We’ve got you covered with our $1500 Learn and Grow fund to support your personal and professional growth, on top of regular lunch & learns, internal courses and workshops, and a coaching program. Our people leaders will work with you to ensure you’re taking advantage of the learning opportunities you want and need
• Competitive benefits package: Our benefits kick in on your first day at Thinkific and include coverage for health, vision, dental, prescriptions, and up to $3000 for your mental health. Our Employee and Family Assistance Program will also take care of you and your family, providing everything to support your well-being
• Parental leave: We care about helping you grow your career AND your family. Family is important to us, and our paid parental leave gives you a little extra help while you're beginning this new adventure. Learn more about our family leave benefits here
• We actually hang out: Thinkers are some of the kindest (and most fun!) people out there. We're into boat parties, hackathons, company retreats, and celebrating everything from Canada Day to Brazilian Carnival. Wherever you’re based, you’ll have opportunities to connect with your team both virtually and IRL
• The bow-wow benefits: Office dogs. Plural. Meet them on Instagram at @dogsofthinkific