Mutual Opportunities
Sales Trainer, Annuities
Boston, Massachusetts
Thank you to our employees for voting us one of the top places to work in Massachusetts for seven consecutive years!
Overview
A career with us means you’ll work alongside exceptional people and be empowered to reach your professional and personal goals. Our employees are at the foundation of what enables MassMutual to deliver on our purpose to help people secure their futures and protect the ones they love.
We embrace the idea that we all are stronger and better through our support for one another. We strive to create a culture where employees feel valued and are celebrated for who they are.
“Since our founding in 1851, mutuality has put our policyowners at the center of everything we do. At our core, we’re a company of people helping people in their time of need, and that spirit extends to the culture we’ve built at our company. Our employees support and rely on each other each day, collaborating to deliver the best solutions for our customers and help millions more secure their future and protect the ones they love.”
Job Description
The Team
MassMutual Strategic Distributors (MMSD) is looking for a Sales Trainer to join our Annuity distribution organization. MMSD works with distributors in the third-party/independent/national broker-dealer/bank market to sell our variable and fixed annuity products through financial professionals. The Sales Trainer will be a source of knowledge for the team regarding the financial services industry, relationship management, growing sales and annuity product knowledge. You will have a strong desire to learn, practice and apply new skills through partnering with talented, experienced sales professionals. You’ll join a team that has a mission to broaden financial wellness and education to communities throughout the country.
The Opportunity
The MMSD Annuities Sales Trainer is an individual contributor responsible for supporting the design, delivery, and continuous improvement of training programs that enable MMSD Annuity sales professionals to perform at the highest. This role focuses on onboarding and ongoing development for Internal Wholesalers, External Wholesalers, and Key Account Managers, ensuring training is practical, relevant, and aligned to business priorities.
In this role, you will partner closely with sales leadership, subject matter experts, and external training vendors, while taking direct ownership of content curation and maintenance across digital training platforms. You will apply adult learning principles to translate strategy, product knowledge, and sales skills into effective learning experiences. You are proactive in your approach to problem solving and timely in your responses to inquiries.
Key Responsibilities but not limited to:
Training Program Execution & Design: Support the design and maintenance of structured onboarding programs for Internal Wholesalers, External Wholesalers, and Key Account Managers. Develop and update ongoing training curricula aligned to product changes, market dynamics, and sales priorities. Apply adult learning theory and instructional design principles to ensure training is learner‑centered, engaging, and applicable in the field. Partner with internal subject matter experts to convert technical content into clear, sales‑ready learning materials.
Training Delivery & Facilitation: Deliver and facilitate training sessions (virtual and/or in‑person) across sales roles and experience levels. Support blended learning approaches that include live sessions, digital learning, and reinforcement tools. Participate in training preparation, logistics, and follow‑up to ensure effective execution and learner engagement.
External Vendor Coordination: Coordinate with external training vendors under the direction of sales or enablement leadership. Support vendor scheduling, program logistics, and content alignment with MMSD Annuities strategy and standards. Ensure externally delivered training complements internal learning efforts and reinforces core sales behaviors.
Learning Platform & Content Curation: Curate, organize, and maintain training content on learning platforms (e.g., Allego or similar tools). Ensure materials are current, accessible, and aligned to role‑based learning needs. Assist with content governance, version control, and organization to promote ease of use for field teams.
Measurement & Continuous Improvement: Collect learner feedback and engagement data to assess training effectiveness. Identify content or capability gaps and recommend updates or enhancements to training materials. Collaborate with stakeholders to support continuous improvement of learning programs.
The Minimum Qualifications
High School Diploma
3+ years’ experience in annuity sales OR 7+ years’ financial services experience in a training, learning or marketing role
Series 6 and 63 at time of application or must obtain within 90 days of hire
Travel required, estimated 20%
The Ideal Qualifications
Experience supporting Annuity training, learning, or enablement programs in a professional or sales environment.
Working knowledge of adult learning principles, pedagogy, and instructional design.
Experience coordinating with external vendors or partners.
Familiarity with digital learning platforms and content management tools (e.g., Allego or similar).
Coursework or certification in Learning & Development, Education, Communications, or related fields.
Experience with digital tools and emerging technologies (Copilot/GenAI, Microsoft 365 or similar tools)
What to Expect as Part of MassMutual and the Team
Regular meetings with the MMSD Annuity Sales Enablement team
Focused one-on-one meetings with your manager
Access to mentorship opportunities
Networking opportunities including access to Asian, Hispanic/Latinx, African American, women, LGBTQ, veteran and disability-focused Business Resource Groups
Access to learning content on Degreed and other informational platforms
Your ethics and integrity will be valued by a company with a strong and stable ethical business with industry leading pay and benefits
#LI-RS1
MassMutual is an equal employment opportunity employer. We welcome all persons to apply.If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
California residents: For detailed information about your rights under the California Consumer Privacy Act (CCPA), please visit our California Consumer Privacy Act Disclosures page.
MassMutual will accept applications on an ongoing basis until such time as a candidate has been offered employment. The job description includes the main duties of this position, which may evolve over time. You may be required to perform other duties not listed.
It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment.
Salary Range: $104,900-$137,700
Hiring Process
Explore
Explore our open jobs by clicking 'search jobs' to find a position that aligns with your experience and skills. You may also consider joining our Talent Network.
Apply
Click the “apply” button on that job posting to complete and submit your application. Your application will be reviewed by a recruiter, which, due to the volume of applications received, may take some time as we carefully consider each application.
Screen
After your application has been reviewed, if you meet the qualifications for the role, a recruiter will reach out to you to start a conversation.
Interview
If you are invited for an interview, you will be scheduled to meet with the hiring manager and hiring team.
Offer
If you are extended an offer to join MassMutual and accept, your start will be contingent upon a satisfactory background check.
Hire
If you accept the offer, we will be so excited to welcome you to the MassMutual community!
If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
By the numbers*
- 85% of employee respondents say they are proud to work at MassMutual
-
90
% of employee respondents say the work they do at MassMutual is meaningful - 85% of employee respondents say they feel encouraged to come up with new and better ways of doing things
*Source: 2025 MassMutual employee engagement survey
Award-Winning Culture
MassMutual is guided by a single purpose: We help people secure their future and protect the ones they love. As a company operated for the benefit of our members and participating policyowners, we are defined by mutuality and our vision to provide financial well-being for all Americans. It’s more than our company structure — it’s our way of life. We are a company of people protecting people. Our company exists because people are willing to share risk and resources and rely on each other when it counts.
We strive to build a thriving community where everyone is valued, included, and feels that they belong.
At MassMutual, we Live Mutual.
How We Work
MassMutual’s flexible workplace approach combines the importance of connecting in person and the flexibility of working remotely. Our hybrid model puts collaboration first with employees coming in at least three days per week to our spectacular campus settings and also enjoying the flexibility of remote Fridays, company-wide remote weeks, and a bank of flexible remote weeks to use throughout the year.
Benefits for the whole you (and your loved ones)
There’s more to your life than your job and there’s more to your aspirations than a paycheck. We take a holistic view of compensation and benefits that provides the flexibility to create a healthy balance in your life for work, family, and community. We offer the benefits you’d expect, like medical, dental, 401(k), and generous vacation time, but we also offer ones you might not expect, like three paid days for volunteering, a $1,250 annual Well-Being Wallet, and up to 320 hours of caregiver leave.
Explore some of our offerings below. Benefit details can be found here.
Why MassMutual?
Kevin
Compliance Consultant
Seth
Service Management Consultant
Kymberly
Head of Experience Journey Mapping
where we work
Springfield Office
1295 State Street, Springfield, MA
Boston Office
10 Fan Pier Blvd, Boston, MA
New York Office
2 Park Ave,
New York, NY
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