Hands-on CTO (Full-Stack, AI)

Pragmatike•Boston, MA

1d•Remote

About The Position

Pragmatike is recruiting on behalf of an early-stage startup building an AI-powered fundraising platform that connects startups, incubators, and investors. The platform leverages data and intelligent matching to help founders identify the right investors, secure warm introductions, and manage their fundraising process end-to-end. By combining AI-driven recommendations with workflow tools, the company aims to make fundraising faster, more efficient, and significantly more predictable. They are product-driven, fast-moving, and focused on building a scalable, high-impact platform from the ground up. We are looking for a hands-on CTO / Founding Engineer to lead the technical vision and execution of the platform. This is not a managerial-only position — it is a deeply technical, builder role. You will be directly responsible for designing, developing, and scaling the core product, including AI-driven matching systems, user workflows, and the underlying data platform. You will work closely with the founders and play a critical role in shaping both the technology roadmap and the product itself.

Requirements

3–5+ years of experience in software engineering (startup experience strongly preferred)
Proven experience as: a CTO, Founding Engineer, or a senior full-stack / AI engineer in a scaling startup
Strong full-stack development skills (frontend + backend)
Solid experience building and integrating AI/ML-powered features
Hands-on experience with cloud infrastructure (AWS) and DevOps practices
Ability to build, ship, and maintain production systems independently
Strong understanding of scalable system design and architecture
Experience or interest in recommendation systems, matching algorithms, or data-driven products
Comfortable working in a fast-paced, ambiguous startup environment
High ownership, autonomy, and product mindset

Nice To Haves

Experience building marketplaces or two-sided platforms
Background in fintech, fundraising, or startup ecosystems
Familiarity with recommendation systems or ranking algorithms
Experience with data pipelines and analytics-driven products
Previous experience scaling a product from early-stage to growth

Responsibilities

Own the end-to-end architecture and technical strategy of the platform
Build and ship core product features across the full stack
Design and implement AI-powered matching and recommendation systems
Develop user-facing features for startups, investors, and partners
Define and optimize scoring, ranking, and data models
Maintain and improve the existing product and infrastructure
Lead cloud infrastructure and DevOps (AWS), including deployments, scaling, and reliability
Ensure performance, scalability, and security of the system
Make key decisions on tech stack, tooling, and system design
Collaborate closely with founders on product direction and roadmap
Gradually build and mentor the engineering team as the company scales