Ai Assistant Jobs in Springfield, MA (NOW HIRING)

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.

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.

$120,400.00 - $198,700.00

1

What is the Opportunity?

As a member of Enterprise AI and Emerging Technologies, 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.

As Director, Product Owner – Enterprise AI Assistants, you'll lead a dynamic team, balancing strategic product leadership with hands‑on stakeholder engagement and delivery. This role requires guiding teams through complex AI capability rollouts while actively shaping the roadmap and priorities for enterprise‑wide AI Assistant platforms. In this highly visible role, we will look to you to:

• Own and evolve the product strategy and roadmap for AI Assistants, ensuring alignment with enterprise AI goals and business priorities.
• Define and maintain a prioritized, execution-ready backlog that drives measurable outcomes for approximately 30,000 enterprise users.
• Play a key role in growing and transforming enterprise AI adoption through structured capability enablement, stakeholder socialization, and continuous delivery.
• Lead a highly effective and collaborative team in supporting a portfolio of AI Assistant tools.

Applicants must be authorized to work for ANY employer in the US. The company does not sponsor/support H-1B petitions, TN, or Forms I-983/STEM OPT, this this role.

• Lead and develop the AI Assistants Team driving enterprise AI Assistant adoption across Travelers.
• Define, prioritize, and maintain a comprehensive product backlog for AI Assistants ensuring execution-ready work aligned to business outcomes.
• Maintain hands‑on involvement in product decisions, backlog refinement, acceptance criteria, and the delivery of AI capabilities across the enterprise.
• Partner with stakeholders across business lines, Legal, Governance, and Gen AI leads to ensure AI Assistant roadmaps align with enterprise strategy and compliance requirements.
• Contribute to product standards and best practices for AI capability enablement, feature rollout, and performance monitoring across teams.
• Troubleshoot and resolve critical product and delivery issues, leading response efforts when adoption, compliance, or platform challenges arise.
• Champion the use of enterprise AI Assistants across the organization through education, stakeholder socialization, and active advocacy.

• Bachelor’s degree.
• Two years of experience in Agile product management.
• Two years of work experience within the discipline being supported (e.g.: Claim, Risk Control, Technology, Project Management, Production, Application Development, etc.).
• Three years of experience articulating and translating business strategy, product vision, and analysis for a product.
• Agile Mindset: Embody Agile core values of openness, courage, respect, focus, and commitment.
• Infuse Agile principles, practices and methodologies to achieve team success.
• Product Mindset: Focus on defining a product value proposition that aligns with and supports the circle/value stream objectives and which is the north star for the team.
• Influence: Ability to influence behaviors of leaders at all levels and without traditional hierarchy.
• Servant Leadership: Foster an environment where individuals thrive as empowered and equal members of a team.
• Communication: Ability to communicate thoughts, concepts, practices effectively at all levels, adjusting as needed to a target audience.
• Collaboration: Expertise working with others in a cross-functional multi-team environment.
• Continuous Improvement: Demonstrate a commitment to continually improve, share learning with others and encourage team development.

• Three years of work experience in related field.
• Three years of experience motivating/influencing teams.

• 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.

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/.