Senior Associate, Sr. Sales Trainer - Distribution Learning & Development

New York Life • New York, NY

20h • Remote

About The Position

Group Benefit Solutions delivers comprehensive insurance and absence management solutions for mid-sized and large companies. Our work fosters a healthier, happier, and more secure workforce, contributing to New York Life’s legacy of being there when we’re needed most. Here, you'll design, implement, and support these solutions directly impacting employees’ lives. At our core, we provide financial security and peace of mind to people through our absence, accident, disability, voluntary benefits, and life insurance solutions. Click here to learn more about Group Benefits solutions.
Role Overview:
The Senior Sales Trainer will serve as the primary facilitator and capability builder for GBS’s Distribution organization. This role is essential to preparing our Distribution and Sales Support teams for the future - where success depends on consultative engagement, AI-driven insights, advanced product positioning, and client experience orchestration.
This individual will lead the design and facilitation of blended learning programs - including self-paced learning, facilitator-led experiences, and manager-enabled on-the-job application - that upskill sales and support professionals to move from transactional and manual processes to strategic, insight-led, technology-enabled roles. The role partners closely with business leaders and managers to ensure learning translates into measurable performance impact. This role supports both large-scale strategic learning initiatives and ongoing business-critical enablement needs, ensuring the Distribution organization can effectively adopt new tools, processes, and capabilities in real time.
The role combines expert facilitation, applied instructional design, AI fluency, and change enablement to drive measurable performance improvement across Distribution.
Candidate Profile
The ideal candidate is a facilitation-first learning professional and hands-on program owner who creates inclusive, engaging environments that drive participation, reflection, and behavior change. This individual not only delivers high-impact programs but also develops content, manages assigned learning initiatives end-to-end, and ensures ongoing accuracy, relevance, and continuous improvement of outcomes. They adapt facilitation approaches in real time based on audience needs, group dynamics, and business context, while maintaining credibility across virtual, hybrid, and in-person settings.
In addition to leading delivery, this role owns end-to-end execution of assigned programs - including planning, stakeholder communication, facilitator enablement, and continuous improvement. The trainer exercises sound judgment in when and how to use learning technologies and AI-enabled tools to amplify connection and insight without detracting from the human-centered learning experience.
Success in this role requires strong stakeholder partnership, independent judgment, and the ability to analyze learning data and performance metrics to drive measurable program improvements. The trainer will evaluate participant feedback, engagement trends, and business impact indicators, and clearly communicate insights and recommendations to leadership as part of ongoing reporting responsibilities.

Requirements

• Bachelor’s degree and/or equivalent professional experience.
• 5+ years of facilitation and learning program experience within a sales, sales enablement, or learning and development environment
• Experience training on AI tools, digital platforms, or technology-enabled transformation initiatives.
• Demonstrated experience facilitating engaging learning experiences across virtual, hybrid, and in-person environments for professional audiences.
• Proven ability to operate independently while influencing across diverse stakeholders without formal authority.
• Strong stakeholder management and relationship-building skills across levels and functions.
• Experience leveraging learning technologies and digital platforms to enhance engagement, scalability, and learner experience.
• Excellent written and verbal communication skills.
• Ability to travel up to 25%, as needed.

Responsibilities

• Design and execute blended learning journeys that integrate self-paced learning, live facilitation, manager-led reinforcement, and applied on-the-job practice.
• Drive adoption of new tools, processes, and capabilities by translating learning into practical application and measurable behavior change in the field.
• Partner with Distribution leaders and frontline managers to reinforce learning application and ensure skill transfer into day-to-day performance.
• Lead engaging in-person, virtual, and blended learning experiences using simulations, scenario-based learning, and applied practice.
• Lead reinforcement, application, and feedback cycles (including manager-enabled on-the-job application) to ensure sustained behavior change and performance improvement.
• Facilitate programs focused on: The execution of Distribution AI enablement programs
• Strategic product positioning and differentiation
• Consultative selling techniques
• Advanced Stewardship delivery using analytics
• Client experience orchestration and renewal readiness
• Digital integration and connectivity discussions
• Train Distribution professionals on consultative engagement techniques that elevate conversations with brokers and clients.
• Enable teams to strategically discuss products, integrations, digital tools, and differentiation in finalist and renewal settings.
• Help sales support functions transition from tactical demos to integration strategy discussions.
• Reinforce behaviors that shift roles from transactional execution to outcome ownership.
• Develop and update training materials focused on AI, consultative skills, product positioning, and client experience.
• Use basic authoring tools (PowerPoint, video capture, documentation tools) to create learning assets.
• Clearly articulate advanced content needs to Learning Experience Designers for scalable development.
• Organize and maintain training content within internal platforms and continuously refine curricula based on field feedback and business priorities.
• Partner with Sales Enablement, Communications, and Knowledge Management to support structured change rollouts.
• Build awareness, reinforcement, and sustainment strategies ahead of major capability shifts.
• Provide feedback to Distribution leadership on adoption barriers and performance gaps.
• Track participation, engagement, and application metrics to measure effectiveness.

Benefits

• We provide a full package of benefits for employees – and have unique offerings for a modern workforce, including leave programs, adoption assistance, and student loan repayment programs. Based on feedback from our employees, we continue to refine and add benefits to our offering, so that you can flourish both inside and outside of work. Click here to discover more about our comprehensive benefit options or visit our NYL Benefits Site.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level