Generative AI Engineer

We’re hiring an AI Engineer to build and scale production-grade LLM systems.

Othello is building at the frontier of real-time generative AI, helping sales teams make better high-stakes decisions in the moments that matter most, while a customer conversation is still happening. Our platform is used by leading sales organizations, including Fortune 500 companies, to deliver live intelligence before, during, and after meetings. We’re an early-stage startup that moves extremely fast, gives people real ownership, and is built for people who want to solve hard technical problems at the edge of what’s possible

This role is for someone with real technical depth, strong ownership, and a serious commitment to mastering their craft. We want a highly driven builder who thrives on hard problems, moves with urgency, and holds a very high bar for quality. Someone resourceful, resilient, and willing to put in the effort required to make complex systems work in production.

What you’ll do

• Build and improve production LLM systems

• Design LLM architectures across prompting, retrieval, orchestration, and inference

• Fine-tune and adapt models for specific use cases

• Create evaluation, testing, and observability systems for quality improvement

• Build automated eval pipelines, benchmarks, and regression testing infrastructure

• Turn ambiguous product problems into reliable AI systems that perform in the real world

What we’re looking for

• At least 5 years of experience building AI/ML systems in production.

• Strong understanding of how LLMs actually work, not just how to call APIs

• Experience deploying LLM-based systems into real production environments

• Experience with fine-tuning, model adaptation, and improving model performance for specific use cases

• Strong experience with AI orchestration, including multi-step workflows, tool use, retrieval, and system design

• Experience designing architecture for LLM-powered systems end to end

• Experience building evaluation frameworks, testing pipelines, and quality measurement systems for LLM applications

• Ability to define meaningful metrics for model quality and system performance

• Experience automating testing and evaluation workflows for prompts, models, and agentic systems

• Deep problem-solving ability and strong engineering judgment

• Comfortable operating in ambiguity and figuring things out fast

• High standards, strong ownership, and a serious work ethic

• Strong desire to learn, improve, and push toward mastery

You should be the kind of person who

• Takes ownership of hard problems and stays with them until they are solved

• Is energized by challenge, speed, and technical difficulty

• Cares deeply about quality and getting details right

• Works with intensity, consistency, and discipline

• Learns aggressively and constantly sharpens their craft

• Wants to build systems that are robust in the real world

What matters most

We are not just looking for someone smart. We are looking for someone deeply committed to the work. Someone who embraces hard challenges, learns fast, works hard, and wants to become exceptional at building AI systems.

This role is for a true builder.