Learning Specialist Jobs in Boston, MA
Learning Specialist jobs in Boston are in strong demand, concentrated in the Longwood Medical Area, Fenway, and Back Bay across higher education, healthcare, and corporate training. Employers hiring right now include Boston University, Trader Joe's, and Boston Medical Center. See the openings below and apply to the ones that match your experience.
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Trader Joe's is your favorite neighborhood grocery store! With almost 600 stores nationwide (and growing), we are the place to be. Looking for something delicious and a friendly conversation? At Trader Joe's, you can find both. We love being your first and favorite place to shop.
What do we do?
Like shopping at Trader Joe's? Then, maybe you'll love working with us. We are looking for an experienced Learning and Development Specialist who is searching to do what they'll love - developing and facilitating content for our Crew Members. Do you have experience in learning and organizational development? Do you love food? If so, read on! We may have the role of a lifetime for you!
Trader Joe's is unlike any place you've ever worked. Trust us on that. The qualified Learning and Development Specialist has at least 5 years of training and content development or educational experience with at least 3 years of leadership experience and is a raving fan of the Trader Joe's concept. A Bachelor's Degree in Organizational Development or Education is required. This role is based in our office in Boston, MA and we have an in office expectation of 5 days a week with travel required up to 33% of the year.
The Learning and Development Specialist is responsible for.
- Facilitating effective training programs, workshops, and learning experiences using a blended learning model to increase engagement and retention.
- Creating a learning environment that is inclusive, thought-provoking, and fun and writing and designing engaging content.
- Demonstrating strong analytical thinking and problem-solving skills to find solutions that impact a large and varied crew member population.
- Collaborating with the development team and other departments to conceptualize and create learning experiences that support Crew development and company growth using a variety of communication vehicles (Zoom, Teams, Email, Phone, LMS, etc).
- Familiarity of a Learning Management System preferred.
- Researching adult learning concepts and leadership development trends.
- Identifying methodologies and training delivery systems to support our store operations.
- Evaluating training to gauge successful outcomes and update curriculum as needed.
- A Bachelor's Degree or equivalent in Organizational Development, Education, or related fields is strongly preferred.
- At least 5 years of training or educational experience and three years of leadership experience.
- Experience facilitating trainings and is confident in public speaking.
- Experience in adult learning principles and designing learnings.
- Strong working knowledge of content management systems, Microsoft Office Suite, and design tools (e.g. Adobe, Canva, etc)
- Experience building and managing a Learning Management System
- Effective time management, organization, communication and interpersonal skills.
- Success in working collaboratively and building and maintaining strong relationships and thrives in a dynamic work environment that includes travel to training locations and stores across the country.
We get a lot of resumes; so to help us get to know you better, please submit your resume and cover letter. When creating your cover letter, please answer these questions:
- What is your favorite Trader Joe's product and why?
- What makes you uniquely qualified for this position?
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Who's Hiring



Learning Specialist Jobs in Boston: Frequently Asked Questions
How do I get a learning specialist job in Boston?
Target Boston's three dominant hiring sectors: higher education institutions clustered around the Fenway and Allston corridors, the Longwood Medical Area's hospitals and research centers, and the financial services and professional services firms headquartered in the Financial District and Back Bay. Candidates who combine instructional design credentials with experience in learning management systems or clinical training programs stand out in this market.
Which companies hire learning specialists in Boston?
Employers hiring learning specialists in Boston right now include Boston University, Trader Joe's, and Boston Medical Center, based on current listings on Migrate Mate as of November 2026. Boston's learning specialist market draws heavily from universities, academic medical centers, and large financial and technology firms, all of which maintain in-house learning and development functions.
Are there remote learning specialist jobs in Boston?
Yes, though it depends on the role: corporate instructional design and e-learning development positions are commonly remote, while roles tied to clinical training or on-campus student support tend to require in-person presence. About 33% of learning specialist openings tied to Boston are remote or hybrid as of November 2026, with the highest share coming from technology and financial services employers.
How can I get a learning specialist job in Boston with little or no experience?
The most realistic entry path in Boston is through program coordinator or training assistant roles at one of the city's many universities or academic medical centers, which frequently hire candidates with relevant coursework or volunteer teaching experience. AmeriCorps placements with Boston Public Schools and tutoring coordinator positions at community colleges also serve as common starting points, building the instructional portfolio that mid-level employers expect.
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