Head of Software Development, Realityworks AI

• Owns the technical architecture, platform roadmap, and engineering standards across cloud applications, embedded systems, physical products, and simulation technologies
• Defines and executes the organization’s AI software strategy, including LLMs, SLMs, speech technologies, computer vision, and intelligent agents
• Leads software delivery and release execution across all product lines, ensuring alignment with business priorities and product roadmaps
• Builds and protects the company’s differentiated technical IP, including patient-state modeling, grading engines, clinical scenario modeling, and AI training-data pipelines
• Directs and optimizes an elastic network of outsourced engineering partners across product management, software engineering, AI/ML, QA, and DevOps functions
• Provides leadership and oversight to the Quality & Validation, Simulation Systems, and Embedded Design teams
• Establishes scalable engineering processes, development standards, platform strategies, and technology roadmaps that support long-term growth
• Partners with product, clinical, hardware, AI, and customer-facing teams to evaluate opportunities, prioritize investments, and deliver innovative customer solutions
• Performs other duties as assigned

• Bachelor’s degree in Computer Science, Software Engineering, Computer Engineering, Electrical Engineering, or a related technical discipline; an equivalent combination of education and progressively responsible software engineering experience will also be considered
• 8+ years of software engineering experience
• Demonstrated experience directing outsourced/offshored engineering teams at scale
• Experience with SaaS platforms and cloud architectures
• Strong understanding of modern AI/LLM technologies

Desired Qualifications

• Medical simulation, healthcare technology, EdTech, or training systems experience
• Experience with conversational AI, speech technologies, or local AI deployments
• Familiarity with hardware/software integration environments
• Experience scaling products from prototype to commercial deployment

Tuition reimbursement, Paid parental leave, Parental leave, 401(k) matching, Paid time off, Dental insurance, Flexible spending account, Gym membership, We offer a robust benefits package, including:

• Employee Stock Ownership Plan (ESOP): 100% company-funded and designed to grow in value as we succeed together
• Health, Dental, and Life Insurance: Comprehensive coverage to support your well-being
• 401(k) Retirement Plan: With company match up to 6%
• Generous Paid Time Off: Over 20 days annually, plus 10 paid holidays
• Wellness Incentives: Gym reimbursement and healthy living rewards
• Family-Friendly Benefits: Paid maternity, paternity, and adoption leave
• Flexible Spending Accounts: Including dependent care coverage
• Disability Coverage: Long-term and short-term
• Education Support: Tuition assistance for continued learning
• Community Engagement: Paid volunteer time and donation matching, * The expected base compensation range for this position is $159,000 - $238,000 annually, determined by experience, qualifications, and geographic location. This position is eligible to participate in the company’s annual bonus program.

RW Thrive is a growth-focused, 100% employee-owned holding company building a network of education-focused businesses, including Realityworks, CreXo, and Realityworks AI. Together, these companies develop experiential learning technology, AI-enabled healthcare simulation, and training solutions used by educators and workforce development programs worldwide. This role is employed by Realityworks AI, a subsidiary of RW Thrive.

The Opportunity

Are you passionate about building technology that makes a meaningful impact? As the Head of Software Development, you will lead the technical vision, strategy, and delivery of an innovative software portfolio spanning Realityworks, CreXo, and Realityworks AI. In this highly visible leadership role, you’ll help shape the future of AI-powered learning and workforce solutions by bringing together cloud applications, embedded systems, physical products, and simulation technologies.

As the organization’s senior software engineering leader, you’ll drive software architecture, AI strategy, engineering excellence, and product delivery while leading the Quality & Validation, Simulation Systems, and Embedded Design teams and guiding a network of engineering partners. Success in this role requires balancing innovation with execution-determining what should be built, when it should be built, and how it should be built to create meaningful customer impact.

Bring your vision, leadership, and technical expertise to help shape the future of learning, workforce development, and AI-driven solutions.

Why Join Us?

When you join Realityworks AI, you become a co-owner in a company that values your contributions and rewards your success. Our employee-centered culture is built on collaboration, innovation, and shared achievement., * This is a remote position with regular travel to our Eau Claire, WI headquarters, expected approximately twice per month for team collaboration, planning, and business meetings. Given this travel cadence, we’re prioritizing candidates based in the Minneapolis-St. Paul area.

Travel Requirements

• Occasional (<10%) domestic and international travel for customer meetings, vendor and partner engagements, and tradeshows

Learn More

• Explore our mission and the impact we’re making in education at www.realityworks.com and crexo.com.

Realityworks AI is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.