Manager of Training

Breaktime United•Boston, MA

1d•Hybrid

About The Position

Breaktime (www.breaktime.org) is a 501(c)(3) non-profit organization dedicated to ending young adult homelessness by providing job and financial security, which leads to housing security. The organization offers a supportive, flexible, and rewarding work environment with benefits like unlimited paid time off, Summer Fridays, 401k matching, fully employer-paid health, dental, and vision insurance, Flexible Savings Accounts, and a hybrid work model. Breaktime is experiencing rapid growth with opportunities for advancement. The Manager of Training will lead the design, iteration, and implementation of young adult learning initiatives, ensuring they align with industry standards and best practices in youth workforce development. This role involves managing the training facilitation team, ensuring operational excellence and administrative compliance, and driving curriculum strategy through collaboration with Program Operations and Impact & Evaluation teams. The ideal candidate is a strategic, systems-focused, and compassionate leader who thrives in dynamic environments.

Requirements

Bachelor’s Degree in a related field AND 3 years of experience in strategic curriculum design, implementation, and auditing.
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.
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 responsiveness to dynamic Associate needs and industry standards.
Outstanding written and verbal communication skills.
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.
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.
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).

Nice To Haves

Master’s Degree in Education (M.Ed.), Instructional Design, Organizational Leadership, or a closely related field.

Responsibilities

Lead the design, creation, and continuous iteration of Breaktime’s educational programming, focusing on curriculum responsive to the needs of Associates in Launchpad and Flight Booster programs.
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 for relevance and effectiveness, incorporating Associate feedback and program data.
Adapt curriculum for multiple modes (virtual, in-person, across geographic locations) to meet Associate needs.
Conduct regular test groups with Associates to gather feedback and iterate on revised curriculum.
Create and sustain a safe, healthy learning environment for young adults experiencing housing insecurity and significant life stressors.
Periodically travel to satellite training locations and community partner sites to oversee in-person program delivery and support facilitation staff.
Oversee facilitation of curriculum delivery in Breaktime’s Launchpad and Flight Booster programs, fostering a culturally responsive and supportive learning environment.
Manage a team of up to 5 direct reports, providing scheduled facilitation observations, coaching on strengths, and goal-setting for growth areas.
Provide ongoing support in the classroom environment as needed and monitor facilitator performance, addressing issues promptly.
Create and implement systems for clear guidelines in team interactions with Associates and ensure appropriate information tracking.
Ensure the training team complies with organizational policies, procedures, and regulatory requirements.
Manage administrative tasks for 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.
Coordinate and facilitate ongoing professional development for the Training Team, 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.
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 Training Team partnerships, including maintaining community partners.
Work collaboratively with other managers to codify best practices and standardize internal operating procedures/policies.
Act as the primary liaison with the Program Operations team and the Impact & Evaluation team to ensure consistent data collection and analyze Associate data/feedback for curriculum improvement.
Collaborate with the Program Operations team to conduct regular audits of curriculum and training processes based on Salesforce metrics.
Ensure 100% staff adherence and compliance with client data entry, data-collection procedures, and case documentation in Salesforce, conducting regular audits.
Sustain a culture of constant improvement within the Training team regarding curriculum, Associate support, and staff development.
Collaborate across Programs verticals to ensure good workflow and support cross-vertical changes.
Perform other duties as assigned or requested.