Technical Project Lead

Position Summary & Responsibilities:

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 MiddleGround’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.

Required Qualifications:

• 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, TypeScript).
• 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 delivery end-to-end, as both builder and lead, with minimal supervision.
• Strong written and verbal communication with both technical and non-technical stakeholders.

Preferred Qualifications:

• Master’s degree in Computer Science or a related field, or relevant technical certifications (cloud, AI/ML).
• Experience building AI, data, or analytics platforms, including data-integration work with ERP, CRM, and Snowflake.
• Hands-on experience with AI/LLM tooling and orchestration frameworks (e.g., LangChain) and AI-assisted development workflows.
• Experience mentoring or leading other developers, including code review and setting engineering standards.
• Exposure to private equity, financial services, or another data-sensitive, regulated environment.
• Experience leading multi-organization technology rollouts or client-facing deployment programs, including hands-on delivery.
• Experience with data engineering and pipelines, event-driven systems, or infrastructure-as-code.

Technical Skills & Competencies:

Languages & Frameworks: Java, Python, JavaScript/TypeScript, SQL; Spring Boot, React, Node.js

AI / LLM: LLM integration (OpenAI, Claude), RAG, prompt engineering, model orchestration (e.g., LangChain)

Cloud & DevOps: AWS or Azure, Docker, CI/CD, observability, security practices

Data & Integration: Relational databases, Snowflake, ERP/CRM integration, ingestion & reporting pipelines

Delivery Leadership: Program planning, roadmap & backlog ownership, risk tracking, executive reporting to the Managing Partner

Team Leadership: Code review, mentoring, setting engineering standards, unblocking the team as a working lead

Domain: Private equity / financial services, multi-organization & portfolio-company rollouts, change management & user adoption