AI Product Chief Architect (OTE $100,000/year USD)

Are you a high-performing software architect who has already made the shift to AI-first development, directing coding agents rather than writing code yourself? Do you want to work for a best-in-class, 100% remote organization with the brightest talent from around the world? If so, then keep reading… At Ironwood Digital , we help social benefit organizations—such as nonprofits, school boards, and government agencies—reach their full potential through technology. Every day, over 150,000 people use our ERP and product platforms to work more efficiently, freeing up time and resources to focus on the good they want to achieve. As our AI Product Chief Architect, you will own the technical architecture of Ironwood Digital 's K-12 Student Information System, a platform carrying decades of battle-tested complexity across VB6, COM, and massive T-SQL, and you'll do it AI-first. This role goes beyond writing requirements, and in fact goes beyond writing code at all: you set the architectural direction, system boundaries, data contracts, and the evolution strategy from legacy to modern C#, and you direct AI agents to navigate the legacy maze and implement your decisions. Most architect roles either ignore legacy reality or drown you in it. Here, you get both: the intellectual challenge of deeply complex systems and the leverage of AI agents to handle the implementation. You'll get a quiet thrill from figuring out what a 400-line stored procedure actually does, then confidently direct agents to reason about it and rebuild it correctly. This is hard, high-rigor work, but if you've already made the shift to AI-first development, this is the role where that shift actually matters, where deep legacy expertise and agentic leverage compound instead of competing. If you've already made the shift to AI-first, this is the role where that shift actually matters. Responsibilities Own the end-to-end technical architecture of Ironwood Digital 's SIS platform, spanning legacy VB6/COM/T-SQL systems and modern C# layers Direct AI coding agents (Claude Code) to implement architectural decisions — you design, agents build Define and enforce architectural guardrails: domain boundaries, coding conventions, and integration patterns for AI agents to follow Review AI-generated code for architectural correctness and behavioral equivalence with legacy logic Participate in requirements and specification reviews, providing architectural sign-off before work begins Drive continuous improvement of agent workflows, prompts, and guardrails Lead technical Deep Dives and RCAs; enforce quality on incoming epics; resolve production outages Requirements 15+ years of software development, 5+ years as architect or technical lead Deep C#/.NET expertise (.NET Core/8, ASP.NET Web API) Heavy hands-on T-SQL — writing, owning, and debugging complex stored procedures where business logic lives in the database Proven ability to navigate large legacy codebases (VB6, VB.NET, COM, Classic ASP) Already working AI-first — uses coding agents as primary development tool in current role Strong async written communication (remote-first team) Bachelor's degree in Computer Science or equivalent experience Nice to have VB6, COM interop, Microsoft Dynamics 365 / Business Central, *Prior SaaS product company experience Benefits We don’t call them perks; they’re just part of what makes working at Ironwood Digital great. We are 100% remote and global. Live your best life wherever that may be, and never lose out on career opportunities because of it. Flexible work hours. We work asynchronously and don’t care when you’re online, just that you deliver great results and are there for our customers. We are dedicated to your growth with consistent and meaningful feedback, support in achieving your personal career goals, and access to leading-edge tools, playbooks, and technology to amplify your experience. Introductions to thought leaders in the space and webinars on cutting-edge tech hot topics. Stipend to help set up your ideal home office. Focus on culture: coffee chats, happy hours, cooking classes, book clubs, and more! We strive to build a team that reflects the diversity of the community we work in and encourage applications from traditionally underrepresented groups such as women, visible minorities, Indigenous peoples, people identifying as LGBTQ2SI, veterans, and people with disabilities. All open roles are for existing vacancies unless otherwise communicated to the candidate. We are committed to keeping candidates informed throughout the process and will notify all interviewed applicants of our hiring decision within 45 days of their interview. Ironwood Digital retains all job postings and related recruitment information for a minimum of three years. Originally posted on Himalayas