Senior Software Developer Ai Trainer Jobs in Springfield, MA

Who Are We?

Taking care of our customers, our communities and each other. That's the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it.

Compensation Overview

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.

Salary Range

$139,400.00 - $230,000.00

Target Openings

1

What Is the Opportunity?

As a member of Enterprise AI & Emerging Tech, you'll be joining a strategic and collaborative team that is passionate about transforming our business and technology capabilities and paving the way for best-in-class technology, data and analytics.
As a Senior Software Engineer for the Enterprise AI Products Value Stream within the Enterprise AI & Emerging Tech organization, you will serve as an organizational technical leader and a driving force behind the engineering standards, architecture decisions, and delivery outcomes of the team. Engineers at this level work across the full arc of AI product delivery - from long-horizon strategic initiatives where the path to production is known and the engineering complexity is high, to engagements that demand rapid, high-quality delivery directly alongside Lines of Business. You will lead stakeholder conversations, shape the technical direction of initiatives, and build collective ownership across engineers, architects, and product owners. This role is for engineers who bring deep, production-hardened AI and machine learning experience, think multiple quarters ahead, and take personal responsibility for elevating the engineers around them.
Applicants must be authorized to work for ANY employer in the U.S. The company does not sponsor/support H-1B petitions, TN, or Forms I-983/STEM OPT, for this role.

What Will You Do?

• Design and lead the delivery of production-grade AI-powered solutions across a range of engagement types - from sustained strategic initiatives requiring deep discovery, architecture ownership, and long-horizon planning, to rapid field engagements focused on integrating LOB workflows with enterprise AI platforms and validating feasibility through working prototypes.
• Drive technical decisions across multiple teams, establishing patterns and engineering standards that are adopted beyond the immediate team and serve as a reference for the broader organization.
• Lead stakeholder conversations with Lines of Business - translating complex technical capabilities into terms that communicate clear business value, and surfacing field intelligence that shapes strategic investment decisions and roadmap priorities.
• Apply production-hardened machine learning experience to the design and evaluation of AI systems - including model selection, fine-tuning, evaluation methodology, feature engineering, and the integration of traditional ML fundamentals alongside modern LLM-based approaches.
• Own the technical quality of what the team ships - driving adherence to nonfunctional requirements including modularity, scalability, observability, recoverability, and testability across all delivered capabilities.
• Mentor engineers across the team and beyond, setting the learning example, defining best practices, and building engineering capability at an organizational level. Advocate for and advance engineering practices across the value stream - including source code management, CI/CD standards, test automation, and modern engineering principles - with an expectation of alignment across teams, not just your own.
• Identify opportunities where technology can drive business value, think proactively two to three quarters ahead, and contribute to the technical strategy of the AI Products value stream.
• Participate in and lead Engineering Chapter events and cross-organizational technical forums, sharing knowledge in a discoverable and enterprise-accessible way.
• Perform other responsibilities as assigned.

What Will Our Ideal Candidate Have?

• 5+ years of software engineering experience with proficiency in Python; additional languages (JavaScript, TypeScript, Java) a plus.
• Hands-on experience with AWS and/or Azure, containerization and orchestration (Kubernetes), RESTful APIs, microservices architecture, and CI/CD tooling (Jenkins or GitHub Actions).
• Production experience designing and delivering agentic workflows, LLM integrations, or AI-powered automations; applied ML experience including model development, training, fine-tuning, and evaluation.
• Demonstrated ability to lead architecture and solution design across teams; advanced delivery skills including design strategy, automated testing, feedback loops, and production health monitoring.
• Strong problem solver - uses data and proofs of concept to find creative solutions, measures impact, and optimizes; comfortable making decisions with broad implications and significant complexity.
• Strong communicator - able to translate complex technical capabilities into business terms, document initiatives clearly, lead stakeholder conversations, and foster inclusive, collaborative team environments.
• Advanced leadership skills - takes ownership in ambiguous situations, influences priorities, develops business partnerships, mentors others, and shares knowledge across the organization.
• Familiarity with Terraform, MongoDB or comparable NoSQL, Temporal or comparable workflow orchestration, and MCP server configurations and multi-agent frameworks.
• Experience with ML observability, drift detection, model performance monitoring, or distributed tracing in production environments.
• Familiarity with zero-trust security principles or secure-by-design development practices in enterprise AI systems.
• Experience establishing or contributing to engineering standards at an organizational level.

What is a Must Have?

• Bachelor's degree in computer science, related STEM field, or its equivalent in education and/or work experience.
• 6 additional years of software engineering experience.

What Is in It for You?

• Health Insurance:Employees and their eligible family members - including spouses, domestic partners, and children - are eligible for coverage from the first day of employment.
• Retirement:Travelers matches your 401(k) contributions dollar-for-dollar up to your first 5% of eligible pay, subject to an annual maximum. If you have student loan debt, you can enroll in the Paying it Forward Savings Program. When you make a payment toward your student loan, Travelers will make an annual contribution into your 401(k) account. You are also eligible for a Pension Plan that is 100% funded by Travelers.
• Paid Time Off:Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
• Wellness Program:The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs. In addition, our mental health program provides access to free professional counseling services, health coaching and other resources to support your daily life needs.
• Volunteer Encouragement:We have a deep commitment to the communities we serve and encourage our employees to get involved. Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.

Employment Practices

Travelers is an equal opportunity employer. We value the unique abilities and talents each individual brings to our organization and recognize that we benefit in numerous ways from our differences.

In accordance with local law, candidates seeking employment in Colorado are not required to disclose dates of attendance at or graduation from educational institutions.

If you are a candidate and have specific questions regarding the physical requirements of this role, please send us an email so we may assist you.

Travelers reserves the right to fill this position at a level above or below the level included in this posting.

To learn more about our comprehensive benefit programs please visit http://careers.travelers.com/life-at-travelers/benefits/.