Senior AI Engineer

Company Overview

Milestone Technologies is a global IT managed services firm that partners with organizations to scale their technology, infrastructure and services to drive specific business outcomes such as digital transformation, innovation, and operational agility. Milestone is focused on building an employee-first, performance-based culture and for over 25 years, we have a demonstrated history of supporting category-defining enterprise clients that are growing ahead of the market. The company specializes in providing solutions across Application Services and Consulting, Digital Product Engineering, Digital Workplace Services, Private Cloud Services, AI/Automation, and ServiceNow. Milestone culture is built to provide a collaborative, inclusive environment that supports employees and empowers them to reach their full potential.

Our seasoned professionals deliver services based on Milestone’s best practices and service delivery framework. By leveraging our vast knowledge base to execute initiatives, we deliver both short-term and long-term value to our clients and apply continuous service improvement to deliver transformational benefits to IT. With Intelligent Automation, Milestone helps businesses further accelerate their IT transformation. The result is a sharper focus on business objectives and a dramatic improvement in employee productivity. Through our key technology partnerships and our people-first approach, Milestone continues to deliver industry-leading innovation to our clients. With more than 3,000 employees serving over 200 companies worldwide, we are following our mission of revolutionizing the way IT is deployed.

Job Overview

We're looking for a Senior AI Engineer to lead the technical build of AI-solutions

Experience: 6-10 Years in Software/ML Engineering, including 2+ years in Gen AI and Document Parsing.

Key Responsibilities

• Design pipelines that process unstructured data.
• Build extraction logic to find key terms and metadata.
• Build multimodal classification (text and image)
• Design the system to scale during catastrophe events
• Build extraction and validation rules.
• Classify routine operational requests such as evidence of insurance, cancellations, payment plan changes, document uploads, and inspection reports.
• Implement rule-driven automation for known, low-risk scenarios.
• Define and tune confidence thresholds for auto-fill, auto-classification, auto-routing, and manual review, including handling for multiple-match results.
• Design human-in-the-loop review, user override, audit logging, and traceability for every AI-suggested or AI-executed action.
• Integrate with shared email inboxes, workflow queues, and other channels.
• Build evaluation sets.
• Protect PII and sensitive claim data through access controls, retention rules, and compliance requirements.
• Work with business architects and client stakeholders.
• Review code and designs, set engineering standards, and mentor AI engineers.

Required Skills

• Strong Python and software engineering fundamentals: APIs, testing, Git, CI/CD.
• Hands-on experience with LLM APIs, including multimodal (vision) models, for extraction and classification.
• Experience with document AI and OCR services and handling low-quality scans.
• Experience building email ingestion pipelines with attachment parsing.
• Solid understanding of confidence scoring, calibration, and precision/recall trade-offs for automation decisions.
• Production deployment on cloud, with queue-based and event-driven architectures that scale under load.
• Ability to explain design choices and risks clearly to claims and underwriting business users.

Nice to Have

• Experience with entity matching with system of records data (Fuzzy matching, identifier validation)
• Fine Tuning or small model optimization for classification at high volume.
• Interest in or exposure to the insurance or financial services domain.
• Cloud AI Certification.
• Degree in Computer Science, IT, Data Science, or a related field.

Compensation

Estimated Pay Range:

Exact compensation and offers of employment are dependent on circumstances of each case and will be determined based on job-related knowledge, skills, experience, licenses or certifications, and location.

Our Commitment to Diversity & Inclusion

At Milestone we strive to create a workplace that reflects the communities we serve and work with, where we all feel empowered to bring our full, authentic selves to work. We know creating a diverse and inclusive culture that champions equity and belonging is not only the right thing to do for our employees but is also critical to our continued success.

Milestone Technologies provides equal employment opportunity for all applicants and employees. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race, color, religion, gender, gender identity, marital status, age, disability, veteran status, sexual orientation, national origin, or any other category protected by applicable federal and state law, or local ordinance. Milestone also makes reasonable accommodations for disabled applicants and employees.

We welcome the unique background, culture, experiences, knowledge, innovation, self-expression and perspectives you can bring to our global community. Our recruitment team is looking forward to meeting you.