Senior AI Engineer: Prototyping, RAG & Stakeholder Lead

Akaasa Technologies; Chicago (IL); On-site; USD 140,000 - 210,000; Full time

Job summary

Akaasa Technologies in Chicago seeks a senior engineer with AI experience to solve business problems using AI and to lead cross-functional efforts. You will help design prototypes, engage with business partners, and drive solutions that scale.

The role emphasizes prompt engineering, RAG pipelines, and collaboration with underwriters to gather requirements, with an emphasis on producing production-ready tools in a team setting.

Qualifications

• 10+ years of professional experience in software engineering, systems design, or technical prototyping.
• 2+ years hands-on experience building AI-augmented tools, RAG pipelines, or prompt-based systems.
• Fluent with Claude Code (preferred) or Cursor or Copilot to accelerate delivery cycles.
• Background in Insurance or Financial Services is highly preferred; underwriting exposure is a plus.

Responsibilities

• Design and implement AI prototypes with prompt engineering, embeddings, and RAG architectures.
• Engage daily with business partners and underwriters to elicit requirements and translate into technical solutions.
• Build functional prototypes with velocity, aiming to production readiness within a cross-functional pod.
• Collaborate with Tech Leads, Architects, and stakeholders in an Agile setting.
• Provide technical guidance and mentorship to pod members to ensure quality and delivery standards.

Skills

AI prompt engineering

Soft skills

Customer engagement

Cross-functional collaboration

Prototype development

Leadership & mentorship

Business stakeholder communication

Tools

Claude Code

Cursor

CoPilot

Python

Job description

Akaasa Technologies in Chicago seeks a senior engineer with AI experience to solve business problems using AI and to lead cross-functional efforts. You will help design prototypes, engage with business partners, and drive solutions that scale.

The role emphasizes prompt engineering, RAG pipelines, and collaboration with underwriters to gather requirements, with an emphasis on producing production-ready tools in a team setting.