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Headway

Learning and Development Manager

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Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. 

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 45,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

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

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience.

Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.

Headway San Francisco, California, USA Office

140 2nd Street, 4th Floor, San Francisco, CA, United States, 94105

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