Job Title: Director of AI & Software Engineering

Location:Singapore/India/Sri Lanka

Type: Full-Time

Travel: Occasional (client meetings, workshops, vendor coordination)

Experience: 10+ years in AI/software engineering, including leadership roles

Role Overview

We are looking for an experienced and driven Director of AI/Software Department to lead our AI and software initiatives across OCR, NLP, and enterprise integration projects — with a strong focus on the insurance industry. This role blends deep technical expertise with strategic vision and excellent client and team management skills.

You’ll be responsible for end-to-end solution delivery, team leadership, client success, and technology partnerships. The ideal candidate should have strong hands-on experience with modern technologies (Python, Node.js, Docker, Kubernetes, APIs) and a solid understanding of cloud and on-premise deployments.

Key Responsibilities

• Lead cross-functional teams of AI engineers, full-stack developers, DevOps, and QA engineers.
• Design, architect, and deliver enterprise-grade solutions in OCR, Natural Language Processing (NLP), and document automation.
• Manage the end-to-end lifecycle of projects for insurance and financial clients, ensuring compliance and business alignment.
• Collaborate with business stakeholders and clients to translate goals into scalable technical solutions.
• Manage vendor relationships — including solution evaluation, onboarding, performance tracking, and contract compliance.
• Oversee DevOps and CI/CD pipelines, ensuring best practices in containerization, deployment, and monitoring.
• Lead cloud and on-premise deployment strategies, system architecture, and integrations via APIs and microservices.
• Represent the technology team in client-facing discussions, RFPs, workshops, and reviews — with confidence in both technical and business conversations.
• Provide mentorship and career development to team members while fostering a high-performance culture.

Required Skills & Experience

• 10+ years of experience in software development/AI with 3+ years in a leadership role.
• Proven delivery of solutions in OCR, document AI, or NLP-related systems.
• Strong understanding of insurance workflows, claims automation, or enterprise back-office systems.
• Expert-level proficiency in Python and Node.js.
• In-depth experience with cloud platforms (AWS, Azure, GCP) and on-premise infrastructure deployment.
• Proficiency in Docker, Kubernetes, and CI/CD pipelines.
• Experience working with REST APIs, microservices, and integration patterns.
• Proven success in managing vendors, evaluating third-party tools, and leading build-vs-buy decisions.
• Excellent communication and leadership skills — capable of aligning technical execution with business strategy.
• Willingness to travel for client meetings, workshops, and vendor engagements.

Preferred Qualifications

• Experience with document classification, OCR model training/fine-tuning, or LLM-based extraction systems.
• Familiarity with common tools in insurance OCR/NLP (e.g., Abbyy, Tesseract, Google Document AI, Amazon Textract).
• Exposure to regulated environments (e.g., HIPAA, GDPR, MAS, HKMA).
• Comfortable with Agile/Scrum methodologies and project management tools (e.g., Jira, Asana).

Iterate.ai is committed to fostering a diverse, inclusive, and equitable workplace. We are proud to be an Equal Opportunity Employer and make all employment decisions—including recruitment, hiring, compensation, benefits, training, promotion, and termination—based on qualifications, merit, and business needs.

We do not discriminate on the basis of race, color, religion, religious creed (including religious dress and grooming practices), national origin, ancestry, citizenship status, sex (including pregnancy, childbirth, breastfeeding, or related medical conditions), gender, gender identity, gender expression, sexual orientation, marital status, age, physical or mental disability, medical condition, genetic information, military or veteran status, or any other characteristic protected under federal, state, or local law.

In compliance with California and Colorado law, Iterate.ai provides reasonable accommodations for applicants and employees with disabilities and for sincerely held religious beliefs, practices, or observances, unless doing so would impose an undue hardship. We also fully support pay transparency and fair pay practices in accordance with the Colorado Equal Pay for Equal Work Act and the California Equal Pay Act.

We believe that a wide range of perspectives makes us stronger, more innovative, and better equipped to serve our customers. We encourage candidates from all backgrounds and communities to apply.