About Milkweed
Milkweed is a bold, early-stage startup reimagining how small businesses, freelancers, and creators run and grow. We bring Fortune 500-level strategy and AI-driven solutions into their daily workflow - without the jargon, overwhelm, or bloated costs. Our mission goes beyond building tech: we’re here to empower people, unlock creativity, and make a lasting impact.
We’re looking for a Founding AI/CTO who is equal parts builder, innovator, and rule-breaker. Ideally, you bring mobile development chops and fluency in infrastructure, architecture, and security engineering. More importantly, you’re relentlessly curious - the kind of person who either figures it out or finds the right person who can. This role is for someone who thrives in a fast-moving, small-team environment, thinks big-picture, and carries a nothing-is-impossible mindset. If building meaningful technology that genuinely helps people excites you - and you want to co-create a future where AI actually serves humanity - this is your opportunity.
What You’ll Do
- Lead the Technical Vision: Define and own the architecture for Milkweed’s AI-powered mobile and web platform.
- Set Strategy & Roadmap: Make high-stakes decisions on product trade-offs (build vs. buy).
- Develop & Deploy AI Pipelines: Build advanced LLM pipelines (RAG, vector DBs, prompt engineering), and own the implementation of MLOps (Docker, Kubernetes, CI/CD, model monitoring).
- Mobile Expertise: Deliver scalable mobile solutions (Swift/Kotlin or React Native/Flutter)
- Cloud Expertise: Architect and management of cloud infrastructure (GCP/AWS).
- Hands-On Innovation: Rapidly prototype, test, and iterate to validate solutions that align with user needs and social impact.
- Collaborate with Leadership: Work closely with the CEO, COO and CSO to bring Milkweed’s mission and product to life.
Who You Are
Versatile & Creative: You’re as comfortable building a system architecture as you are brainstorming new ideas for product design and user experience.
Big Thinker: You thrive on envisioning bold, disruptive solutions while staying grounded in execution.
Heart-Driven Innovator: You care deeply about building technology that helps people, with a philanthropic outlook on innovation.
Team-Oriented: You enjoy working in small, tight-knit teams, where collaboration and agility are key.
Nothing-Is-Impossible Attitude: You approach challenges with optimism, resilience, and a bias for action.
Mission-Aligned: You want to make a tangible difference in the world through your work.
What You Bring
- Proven technical ability, whether you’re a college graduate or a seasoned professional, your confidence, creativity, and portfolio of work matter most.
- Full-stack mobile development (Swift/Kotlin or React Native/Flutter), or demonstrable experience building mobile apps that scale.
- Cloud expertise with GCP or AWS, with the ability to design secure and resilient architectures.
- Hands-on experience with modern AI/LLM pipelines (RAG, vector databases, prompt engineering) or strong interest and capacity to quickly master these technologies.
- MLOps knowledge: Docker/Kubernetes, CI/CD workflows, and model monitoring.
- Product trade-off expertise: A pragmatic approach to deciding when to fine-tune, call an API, or build from scratch.
- A track record of delivering AI-enabled SaaS or consumer applications - or strong, verifiable examples of innovative projects that showcase your potential.
- A collaborative, entrepreneurial spirit with the willingness to grow into a true partner and co-founder.
- A strong network of engineers or advisors (or the resourcefulness to build one).
Bonus: Experience as a technical co-founder, early-stage startup builder, or someone who has worn multiple hats to bring a product from idea to launch.
Compensation & Perks
Equity Ownership: 15–25% as a founding team member.
Mission-Driven Culture: Work on tech with purpose, impact, and heart.
Creative Freedom: Help shape the product, team, and company from the ground up.
Flexible Location: Work remotely
