Head of Software Development, Realityworks AI

Join Our Team at Realityworks AI! 

Who We Are

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 a curious, strategic, and execution-driven technology leader who loves building great teams and great products?

As the Head of Software Development, you'll serve as the senior software engineering leader across Realityworks, CreXo, and Realityworks AI, helping shape the future of AI-powered learning, workforce development, simulation, and connected product solutions.

This is a working manager role for a leader who enjoys balancing strategy with execution. You'll be responsible for defining technical direction, building and leading engineering teams, guiding external development partners, and driving the successful delivery of software solutions that create real customer impact. You won't simply oversee the function from a distance. You'll stay close enough to the technology, architecture, AI initiatives, and delivery efforts to remove obstacles, make informed decisions, and help teams succeed.

We're looking for someone who is equally comfortable discussing product strategy with business leaders, challenging technical decisions with engineers, and helping teams navigate ambiguity to execute quickly and effectively. Success in this role requires strong technical judgment, a bias for action, and the ability to build a high-performing software development organization without overcomplicating the process.

If you're energized by solving complex problems, exploring emerging technologies, leading teams, and turning ideas into reality, this is an opportunity to make a meaningful impact while helping shape the future of learning and workforce development.

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.
 

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

Compensation

• 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. 

Work Location 

• Realityworks headquarters is located in Eau Claire, WI. This is a remote position, working from a home office, with occasional in-person visits to headquarters as business needs require. There is no fixed recurring in-office schedule. Candidates must reside in one of the following states: Florida, Indiana, Kansas, Massachusetts, Minnesota, North Carolina, Pennsylvania, Rhode Island, South Carolina, Texas, Virginia, or Wisconsin

Key Responsibilities

• 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 

What You’ll Bring

• 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

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 www.crexo.com. 

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