Manager of Training in Boston, Massachusetts at Breaktime

Full-Time, $70k-$90k Annualized Salary, Exempt, Hybrid (Minimum 3 days a week in person), Full benefits from Day 1

Organization Overview

Breaktime (www.breaktime.org) is a 501(c)(3) non-profit working to break the cycle of young adult homelessness by equipping young adults with the job and financial security they need to establish housing security. Our vision is a world without young adult homelessness. By providing employment, wraparound services, and financial support, Breaktime ensures that every young person has the tools they need to achieve job, financial, and long-term housing security.

Breaktime prides itself on our supportive, flexible, and rewarding work environment. We offer valuable benefits such as unlimited paid time off, Summer Fridays, 401k matching, 100% employer-paid health, dental, and vision insurance, Flexible Savings Accounts, and flexible hybrid work. Breaktime is rapidly expanding as an organization, and we believe there are significant opportunities for advancement.

Overview

The Manager of Training oversees the training vertical at Breaktime, including leading the design, continuous iteration, and implementation of young adult learning initiatives informed by industry standards and best practices in youth workforce development across multiple platforms. The role manages the training facilitation team, ensures operational excellence and administrative compliance, and drives data-driven curriculum strategy by serving as the primary liaison with the Program Operations and Impact & Evaluation teams.

Roles & Responsibilities

The Manager of Training is a strategic, systems-focused, and compassionate leader who thrives in fast-paced and ever-evolving environments. We are seeking an individual to lead the design, iteration, and implementation of Breaktime’s training and curriculum services while fostering a supportive and collaborative learning environment for both staff and Young Adults (Associates). This role is visionary/strategic, process-oriented, and collaborative.

Curriculum Development and Program Execution:

• Lead the design, creation, and continuous iteration of Breaktime’s educational programming with a focus on curriculum that is responsive to the needs of Breaktime Associates engaged in our Launchpad and Flight Booster programming.
• Collaborate with subject matter experts to ensure curriculum content aligns with industry standards and best practices for youth workforce development.
• Continuously assess and update curriculum materials to ensure relevance and effectiveness by actively incorporating Associate feedback and program data.
• Adapt the curriculum to be accessible in multiple modes (virtual, in-person, and across geographic locations) to meet the needs of Associates who access the program in those ways.
• Conduct regular test groups with Associates to gather feedback and iterate on the revised curriculum.
• Effectively create and sustain a safe, healthy learning environment for young adults experiencing housing insecurity and other significant life stressors.
• Travel periodically to various satellite training locations and community partner sites to oversee in-person program delivery and support facilitation staff.

Facilitation Oversight and Program Management:

• Oversee facilitation of curriculum delivery in Breaktime’s Launchpad and Flight Booster programs to foster a learning environment that is culturally responsive to the unique needs of young adults experiencing housing insecurity while meeting learning objectives.
• Manage a team of up to 5 direct reports by providing scheduled facilitation observations to assess strengths and create goals to address areas of growth related to classroom management and ensuring a supportive learning environment for Associates.
• Provide ongoing support in the classroom environment as needed.
• Monitor facilitator performance and address any performance issues promptly.
• Create and implement systems to ensure the team has clear guidelines in their interactions with Associates and that information is being appropriately tracked.

Administration and Management:

• Ensure the training team complies with organizational policies, procedures, and regulatory requirements.
• Manage administrative tasks related to team supervision, including scheduling, payroll, and performance evaluations.
• Conduct weekly 1x1 and group supervision with team members to provide guidance, address challenges, and foster professional growth.
• Facilitate and monitor individualized goal-setting/tracking with team members and complete employee evaluations at regularly scheduled intervals.
• Coordinate and facilitate ongoing professional development for the Training Team in collaboration with the Assistant Director of Workforce Development, with a minimum of 4 training sessions annually.
• Act as a role model to staff and be available to assist in day-to-day activities as needed.
• Serve as an advocate for Training Team Staff and support staff retention by fostering a collaborative, supportive work environment.
• Serve as a liaison to ensure the successful administrative oversight of the Training Team partnerships, including maintaining community partners.

Data-Driven Strategy & Operational Excellence:

• Work collaboratively with the Manager of Program Operations, Manager of Young Adult Services, and Manager of Workforce Partnerships to codify best practices and standardize internal operating procedures/policies to ensure responsive service provision throughout the Associates’ engagement in the program.
• Act as the primary liaison with the Program Operations team and the Impact & Evaluation team to ensure consistent data collection for program outputs and analyze Associate data and feedback to improve curriculum design.
• Collaborate with the Program Operations team to conduct regular audits of curriculum and training processes based on metrics captured in Salesforce.
• Ensure 100% staff adherence and compliance with client data entry, data-collection procedures, and case documentation in Salesforce, conducting regular audits to maintain accuracy.
• Sustain a culture of constant and never-ending improvement within the Training team in our curriculum, our support of Associates, and their staff development.
• Collaborate across Programs verticals to ensure good workflow and support cross-vertical changes.

Other duties as assigned or requested.

Reports to: Assistant Director of Workforce Partnerships

Supervises: Up to 5 Direct Reports

The Manager of Training is an organized, detail-oriented, and skilled leader who is excited to demonstrate Breaktime’s values of Young Adult First, Radical Inclusivity, and Collaborative Innovation while working with a team of aligned individuals to address the educational and professional development needs of Breaktime Associates.

Qualifications:

• Bachelor’s Degree in a related field AND 3 years of experience in strategic curriculum design, implementation, and auditing AND 2 years of experience in a teaching or high-quality professional training/facilitation role with young adult learners.
• 2 years of managerial experience overseeing a team of direct reports, including performance coaching and professional development OR equivalent transferable experience that provides proof of the ability to manage people.
• Proven ability to lead and oversee the delivery of curriculum across multiple modalities (virtually and in person) while fostering a culturally responsive and trauma-informed learning environment.
• Demonstrated success in structuring program logistics, running feedback mechanisms (e.g., test groups), and ensuring curriculum is responsive to dynamic Associate needs and industry standards.
• Outstanding written and verbal communication skills to effectively manage partnerships, conduct training, and report out on program strategy.
• An agile, highly-organized leader with a proven track record of strategic delegation, fostering supportive team cultures, and proactively solving complex problems while managing competing priorities and tight deadlines.
• Advanced proficiency with the Google Workspace and demonstrated experience leveraging CRM systems (e.g., Salesforce) for compliance, data entry, and case documentation.
• Demonstrated experience using data to analyze program outcomes, inform curriculum strategy, and ensure compliance with complex grant regulations (e.g., WIOA, City of Boston SuccessLink).
• Exceptional skills as a liaison and collaborator, with experience working across internal stakeholder groups to standardize policies and drive organizational goals.
• Ability to travel occasionally across the locations we serve; valid driver’s license and access to reliable transportation preferred.
• [Preferred] Master’s Degree in Education (M.Ed.), Instructional Design, Organizational Leadership, or a closely related field.

Physical Requirements & Work Environment:

Candidates must be able to perform the essential physical demands of this role, with or without reasonable accommodation:

• Ability to sit/stand for extended periods during in-person training sessions and classroom observations.
• Ability to routinely lift, carry, and set up training materials or equipment (up to 20 lbs).
• The work environment is a mix of a standard office/remote setting and active classroom floor.

Breaktime carefully considers a wide range of compensation factors, including but not limited to prior experience, skills, expertise, location, internal equity, and other considerations permitted by law. The comprehensive remuneration details, inclusive of benefits, will be communicated upon finalization of the employment offer.

We value and welcome equivalent lived and professional experience. Research suggests that qualified women, marginalized identities, Black, Indigenous, and/or Persons of Color (BIPOC), may self-select out of opportunities if they don’t meet 100% of the job requirements. We believe in diversity and inclusivity at Breaktime, and encourage candidates from various backgrounds to apply if they believe they have the necessary skills to thrive in this role.

Breaktime champions radical inclusion. We strive to be an organization where everyone feels welcome, particularly those who are most often excluded and discriminated against. As an Equal Opportunity Employer, Breaktime does not discriminate in its employment decisions on the basis of housing status, race, color, gender, national origin, age, religion, creed, disability, veteran’s status, sexual orientation, gender identity, gender expression, or any other basis that would be in violation of any applicable federal, state, or local law.

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.