Technical Project Lead

Located in Lexington, KY, this role is a hands‑on Technical Lead who builds our internal AI platform alongside the development team and owns the program end‑to‑end. The Technical Lead writes production code as a full peer to the developers while also planning the work, coordinating delivery, driving the firm‑wide rollout, leading the repeatable deployment across our portfolio companies, and reporting directly to the Managing Partner on progress, risks, and decisions.

• Serve as a hands‑on developer on the AI platform — designing and writing production code across backend services, APIs, data models, and front‑end interfaces alongside the development team.
• Oversee the execution of the technical direction and architecture for the platform and establishing engineering standards the team codes to.
• Own the program plan, scope, timeline, and budget, translating business needs from the Managing Partner and stakeholders into a technical roadmap and prioritized backlog for the team.
• Report out directly to the Managing Partner on program status, technical progress, risks, and key decisions — translating engineering detail into clear, executive‑level updates.
• Lead the developers day to day — reviewing code, unblocking technical problems, and keeping delivery on track against committed milestones as a working member of the team.
• Integrate large language models and AI services into the platform — applying retrieval‑augmented generation (RAG), prompt engineering, and orchestration to deliver reliable, context‑aware features.
• Build and maintain development, staging, and production environments; containerize and deploy services to the cloud; and establish CI/CD, observability, and security practices for the platform.
• Design and build connectors and integrations to approved internal systems and data sources, keeping the platform’s workflows and pipelines moving.
• Collaborate with Managing partner on the firm‑wide rollout to approximately 100 internal users — sequencing onboarding, training and change management, and adoption.
• Lead the rollout of the AI platform across Middle Ground’s portfolio companies on an ongoing basis — planning and personally executing each deployment from kickoff through go‑live.
• Perform hands‑on integration work at portfolio companies — connecting their systems of record (ERP, CRM, Snowflake) through ingestion, normalization, and reporting pipelines.
• Partner with and enable portfolio‑company technical and executive teams — providing technical direction and training so their staff can own and sustain the platform after deployment.
• Own and continuously refine the repeatable deployment playbook and reusable technical templates, capturing lessons learned to make each successive portfolio rollout faster and more consistent.
• Write clear technical and program documentation, and handle all firm and portfolio‑company data in accordance with confidentiality and data‑security requirements.

• Bachelor’s degree in Computer Science, Engineering, or a related field, or equivalent practical experience.
• 7+ years of professional full‑stack software development experience delivering production‑grade applications, with at least some experience leading a team or program.
• Strong hands‑on full‑stack development skills — backend services and APIs (e.g., Java/Spring Boot, Python, or Node.js) and modern front‑end (e.g., React, Type Script).
• Demonstrated experience integrating LLM APIs (OpenAI, Claude, or comparable) into real applications — including RAG, prompt engineering, and sound reasoning about cost, latency, and reliability.
• Hands‑on cloud experience (AWS or Azure), including containerization (Docker) and CI/CD pipelines.
• Proven ability to lead delivery of a technical program — owning plan, scope, timeline, and priorities while remaining hands‑on in the code.
• Experience leading organizational rollouts, change management, and user adoption for new systems or platforms.
• Comfort reporting to and engaging senior executives — including the Managing Partner and portfolio‑company leadership — translating technical detail into clear status and recommendations.
• Proven ability to work independently and own…