Learning and Development Manager

Squarespace is seeking an experienced Learning and Development Manager for our Training and Development team. You will be responsible for helping evolve our company onboarding and leadership development programs.

You will provide guidance to various teams throughout Squarespace to help them meet their objectives, and establish a rhythm of continuous training that reinforces our core values. This position reports to the Director of Training and Development, and will be based in our New York office. 


  • You'll design learning and development initiatives by partnering with leaders across the organization to identify business and culture objectives
  • Develop a training curriculum, and revise to reflect business need or organizational changes as necessary
  • Recommend the best training solutions, which may include: e-learning, classroom training, 1:1 sessions, action learning, and a blended approach
  • Draw on internal and external resources to ensure the design and delivery of the highest quality programs, materials, and other learning and development resources and activities, including e-learning, self-paced, ILT and other facilitated learning activities
  • Act as a lead instructional designer to create cutting-edge training
  • Regularly align with our recruitment and people teams to refine the talent hiring and onboarding experience
  • Mentor training team members across all office locations to ensure consistent training globally
  • Identify opportunities for improvement within the training team, and provide appropriate coaching or educational resources 
  • Proactively leverage technology, industry best practices, external networking, and alternative learning methods to continuously evolve Squarespace's learning and development activities
  • Assess relevant training needs, including assessment methods and measurement systems
  • Work with the team to optimize processes, incorporating automations where possible 
  • Monitor and report on team activities, costs, and the performance of training initiatives
  • Evolve training assessment and evaluation methods to measure individual success and program effectiveness, continuously improving resource allocation
  • Roughly 20% travel required


  • 7-12 years of on-the-job training facilitation and development experience
  • Exceptional written and oral communication skills; confidence presenting to large audiences
  • Self-motivation and the ability to inspire a team
  • Impeccable organizational and project management skills
  • Well-versed in adult learning theory, with a passion for translating your thoughts into engaging resources
  • Technical writing experience and musings on how to transform those around you into knowledgeable communicators
  • Experience utilizing e-learning software and solutions for training and continued education
  • Experience working with third parties, including consultants and vendors
  • A portfolio that demonstrates key aspects of your previous training experiences, including experience in management/leadership development
  • An eye for design, with experience creating multimedia training materials
  • Experience with the ADDIE Model, Thiagi’s 4-door method, and Kirkpatrick’s
  • Participation in training organizations such as eLearning Guild, ATD or SHRM would be a bonus
  • Degree, CIPD or CTP qualified, or equivalent

Resumes without cover letters will not be considered. 


Squarespace makes beautiful products to help people with creative ideas succeed. By blending elegant design and sophisticated engineering, we empower millions of people — from individuals and local artists to entrepreneurs shaping the world’s most iconic businesses — to share their stories with the world. Squarespace’s team of more than 570 is headquartered in downtown New York City, with offices in Dublin and Portland. For more information, visit www.squarespace.com/about.

  • Health insurance with 100% premium covered
  • Flexible vacation & paid time off
  • Equity plan
  • 401(k) plan with employer match
  • Free lunch and snacks
  • Dog-friendly workplace
  • And more

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customer base, but we also strive for the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender, gender identity or expression, or veteran status. We are proud to be an equal opportunity workplace.


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