Learning and Development Manager

About The Role: 

Headway is looking for a Learning and Development (L&D) Manager to join the People team to drive key learning and development programs for Headway employees. This role will require someone who can both design e-learning and async content and facilitate live sessions, as well as strategically use outside resources to support the Learning and Development roadmap. You will work closely with the Director, People Operations and Strategy, as well as the People Leadership team, to deliver both ongoing and one-off programs that support our managers and employees. This is a unique opportunity to work with managers from across the organization and Headway leadership to develop both targeted and company-wide initiatives.

We’re looking for a leader with expertise in Learning and Development programs, who takes initiative, is able to put together thoughtful training sessions, and can navigate ambiguity.  As the first L&D hire on the People team, you are critical to establishing new programs and scaling our initiatives as Headway continues to grow our workforce.

You Will

• Design and facilitate the core Manager Training program for 200+ managers and additional manager-focused sessions, including coordinating monthly manager meetings
• Organize and deliver comprehensive training sessions across various skills and competencies, including Headway’s cultural principles
• Facilitate employee growth by developing Individual Development Plan frameworks and enablement materials, while managing a library of internal and external L&D resources
• Oversee L&D operations including budget management, vendor relationships, and virtual training tools, while administering company L&D policies, training completion administration and stipends
• Act as the primary subject matter expert on internal learning management systems, maintaining best practices and system optimization
• Collaborate with departments to align training calendars, provide consultation on internal training programs, and ensure consistent quality across all learning initiatives

You’d be a great fit if…

• You have 7+ years of experience in Learning and Development focused on program design and delivery
• You are deeply knowledgeable on best practices when it comes to the People Management, People Development, Training, and Instructional Design best practices
• You are able to create effective materials and sessions from the ground up, and also exercise sound judgement on when to bring in outside resources
• You are highly organized and detail-oriented with the ability to manage multiple large-scale L&D programs simultaneously
• You are strategic thinker who understands the bigger picture, but also operates and executes tactically 
• You function well in a high-paced environment and are able to quickly adapt to changing priorities and situations
• You’re skilled in tailoring communication for all audiences and influencing key decision-makers through clear, impactful messaging
• You collaborate, build credibility, and trust across all levels of the company

Pay Transparency Clause

Compensation and Benefits:

• The expected base pay range for this position is $116,960 - $172,000, based on a variety of factors including qualifications, experience, and geographic location. 

  We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development