Director of Training and Professional Development

Open Sky Community Services • Worcester, MA

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About The Position

We are seeking an experienced and passionate Director of Training and Professional Development who understands the heart of human services and how strong operations support meaningful impact. Our ideal candidate brings hands-on field experience, a deep appreciation for adult learning, and a talent for designing engaging, effective training. With expertise in instructional design and training evaluation, this leader inspires growth, builds capability, and helps teams thrive through thoughtful, well-crafted learning experiences. The Director of Training and Professional Development brings learning to life by shaping and leading a dynamic, organization-wide learning strategy. This role champions engaging onboarding experiences, supports compliance with confidence, builds future-ready leaders, and fuels continuous professional growth. Through a mix of in-person and virtual learning experiences, the Director ensures training is accessible, impactful, and inspiring. Partnering closely with leaders across the organization, this role aligns learning initiatives with business goals, evolving workforce needs, and regulatory requirements—helping employees grow, thrive, and succeed. Other Key responsibilities:
Hire, supervise, evaluate and develop a team of training professionals and facilitators.
Design and ensure the delivery of comprehensive competency based training
Evaluate quality of current training offerings and provide feedback to trainers on quality improvement when necessary.
Interface with organizational leaders to assess unique and ongoing training needs
At Open Sky Community Services, we open our doors, hearts, and minds to the belief that every individual, regardless of perceived limitations, deserves the chance to live a productive and fulfilling life.
Open Sky is on an anti-racist journey, committed to learning, living, and breathing inclusion, opportunity, diversity, racial equity, and justice for ALL.
At Open Sky, you’ll join over 1,300 compassionate and highly trained professionals who put innovative, evidence-based practices to work in ways that positively impact our communities across Central Massachusetts and beyond.
As a trauma-informed organization, Open Sky strives for transparency and sensitivity to the experiences of those we interact with. Self-care is encouraged, and we are committed to providing a positive work culture that is focused on continuous learning and the value of diverse perspectives.
Open Sky is proud to be an industry leader in pay and benefits. Open the Door to Possibility and begin your career with Open Sky today!

Requirements

• Bachelors Degree in Human Resources, Education, Organizational Development or a related field, required
• Minimum of 5 years advanced knowledge of human service business operations with experience in the field, required.
• Strong knowledge of adult learning principles, instructional design and training evaluation, required.
• Excellent written and verbal communication, organizational and project management skills, required.
• Valid Drivers License and acceptable driving history, required.

Responsibilities

• Hire, supervise, evaluate and develop a team of training professionals and facilitators.
• Design and ensure the delivery of comprehensive competency based training
• Evaluate quality of current training offerings and provide feedback to trainers on quality improvement when necessary.
• Interface with organizational leaders to assess unique and ongoing training needs

Benefits

• Excellent Supervision (Individual and Group), Professional Development, and Training Opportunities
• Generous paid time off plan – you start with 29 days (almost 6 weeks!) in your first year, including 12 paid holidays. Increases to 32 days in your 2nd year, and the current maximum is 43 days (OVER 8 WEEKS!)
• We pay for your higher education! Ask about our Tuition Reimbursement Program, and reimbursement for a variety of Human Services certifications.
• Medical, Dental and Vision Insurance with Prescription Plan
• 403b Retirement Plan with Employer Match
• Life Insurance (100% Employer-Paid)
• Eligible employer for the Public Student Loan Forgiveness Program
• And more!

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 1,001-5,000 employees