Jobs at Milkweed

The CTO at Milkweed is more than a technical lead - they are a builder, innovator, and culture carrier who will help shape the future of how small businesses grow. This role is responsible for translating our vision into a powerful, accessible platform that brings executive-level strategy to small business owners everywhere, without the jargon or gatekeeping. As our CTO, you’ll architect and scale the core technology behind Milkweed: an AI-powered platform designed to be simple, intuitive, and trustworthy. You’ll make key decisions on infrastructure, security, and product development, balancing innovation with reliability. But more importantly, you’ll be a partner in leadership - working closely with the founding team to drive product strategy, define milestones, and ensure that every line of code connects back to our mission of bold, accessible growth. We’re looking for someone who thrives in early-stage environments: hands-on, adaptable, and unafraid to learn or find the right collaborator when needed. Curiosity, ownership, and creative problem-solving matter as much as technical expertise. This isn’t just about building an app - it’s about building a movement that levels the playing field for small business owners. If you’re the kind of leader who sees technology as a tool for empowerment, who values clarity over complexity, and who wants to be part of a team that pushes limits with the same discipline as athletes, then Milkweed is where you can make your impact.