Head of Software Engineering (Health Tech)

Who We Are We are a fast-growing vertical SaaS company that leverages innovation and disruptive technologies to improve consumer experiences, outcomes, and predictability in elective medicine. Our team thrives on challenges, embraces change, and is dedicated to transforming our industry. Ironwood Digital is scaling rapidly, and the way we build is changing just as fast. We are moving from a world where product hands off specs and Figma files to engineering, to one where product and design build working software alongside engineering. This role is built for that future, but it starts, as great product work always has, with deep knowledge of the space and the customer. While we are a remote-first company, we can currently hire candidates only in the following U.S. states: CA, CO, FL, GA, IL, OK, OR, PA, RI, TX, UT, and WA. We hope to expand to additional states in the future. Who We Are Looking For We are looking for a visionary Head of Engineering to lead, mentor, and scale our globally distributed engineering team—primarily based in Latin America. This is a high-impact leadership role that requires deep technical expertise, strategic thinking, and experience challenging the team to do better, setting a high bar for accuracy, and ensuring technical decisions are thoroughly validated. You’ll be responsible for driving architectural direction, growing a skilled team developing in the .NET ecosystem, and implementing intelligent automation across Ironwood Digital ’s platform. If you thrive in ambitious and hard-working environments and know how to build, scale, and mentor teams with business objectives/goals on top of mind while keeping operational excellence and innovation in mind— this role is for you. Responsibilities Leadership & Strategy Own the technical roadmap in close collaboration with the product team and executive leadership. Set the vision for engineering culture, delivery standards, and high development velocity. Ensure engineering goals align with internal Ironwood Digital priorities as well as clinic partners. Foster cross-functional collaboration with UX/UI teams. Team Management Lead a 30+ person engineering team (and growing) across multiple time zones, with a majority based in LATAM. Hire, mentor, and develop engineering managers and high-performance contributors. Foster a culture of learning the business and acting on behalf of the business with high accountability Manage and deliver routine performance evaluations and performance improvement plans. Technical Execution Oversee architecture and execution of scalable, secure, and maintainable systems. Create new products from scratch & integrate and adapt API driven solutions to scale product portfolio and address partner needs for ERP systems Own DevOps, infrastructure, and data security strategies. Help develop and build our our IT department including, MDM, SSO, and HIPAA compliance. Innovation & AI Automation Stay at the forefront of AI trends and translate them into tangible platform improvements. Healthcare SaaS Ensure the engineering org builds GDRP, HIPAA, and other-compliant, scalable SaaS solutions for the US plastic surgery practices. Requirements 10–15+ years in software engineering, with at least 5 in senior engineering leadership roles. Experience building and scaling engineering teams in high-growth startup environments. Deep technical knowledge and hands-on experience with the .NET stack , including: ASP.NET Core, C#, Web API, Entity Framework, Python and SQL Server Proven success scaling teams and systems in startup SaaS businesses, preferably during $10M–$80M growth phases within 5-7 years. Cloud deployment in Azure or AWS Background in healthcare tech, especially SaaS products. Experience overseeing ERP implementation and AI/ML integrations. Experience defining technical plans and org-wide strategies from scratch. Deep operational discipline: knows how to spot execution issues and course-correct decisively Benefits What We Offer At Ironwood Digital , we believe in supporting our team’s well-being and growth through comprehensive benefits and a collaborative, people-first culture. As a globally remote company, we prioritize flexibility, inclusivity, and teamwork rooted in the Ironwood Digital principles. Benefits & Perks: Healthcare coverage for you and your family Paid time off (PTO) and paid holidays Performance-based bonuses and company equity opportunities Fully remote work environment with flexible schedules Collaborative and thriving team culture guided by Ironwood Digital ’s core values Why Ironwood Digital ? Joining Ironwood Digital means becoming part of a high-performing, ambitious team that works hard, achieves extraordinary results, and enjoys the rewards that follow. Every employee receives equity, aligning us all in our shared success. Promotions and growth opportunities are limitless, driven only by your performance and dedication to our core principles: We do what is best for the company, not what is best for individuals of the company—we take pride in our work, but not in pride