AI Development Lead

Dear Professionals,

AI is changing how software is built, but tools alone don’t create lasting advantage. At Sideline, our developers already use AI daily, and we’re seeing real productivity gains. But we’re at a crossroads. Either AI remains ad hoc and fragmented, or we organize it into a structural advantage.

That’s why we’re introducing a new role: AI Development Lead

Why this role exists;

Across the industry, AI adoption follows a familiar pattern:

• Individual experimentation
• Ad hoc team usage
• Fragmentation and loss of advantage

• The teams that win don’t just use AI, they systemize it.
• This role ensures AI becomes a repeatable, scalable, and durable productivity multiplier, not a short-lived boost.

Your mission;

As AI Development Lead, you will own how Sideline builds software with AI.
This is not a tooling or experimentation role; it’s a productivity, quality, and scale role with real ownership.

What you’ll do;

• Design reusable AI development workflows (code generation, refactoring, testing, debugging, documentation, reviews)
• Build and maintain a central AI knowledge system (prompts, patterns, lessons learned)
• Accelerate onboarding and team capability through workshops and coaching
• Ensure quality and consistency in AI-assisted development
• Evaluate new tools and models based on measurable impact

Who we’re looking for;

• Senior software engineer with strong production experience
• Deep understanding of modern development workflows
• Hands-on experience using AI in daily development
• Strong at systemizing, documenting, and teaching
• Influential, pragmatic, and execution-focused

Work Location: In person