Director, Learning & Development

Squarespace, New York, NY

Help the world share their story

Squarespace’s People team is seeking a Director of Learning & Development to work closely with our business leaders to design and execute engaging employee development programs that are tied to our business strategy on a global scale. 

You will have the ability to zoom out and keep strategic focus on scaling for growth and retention. You’ll also work hand-in-hand with the broader People team leaders on projects and initiatives to cultivate our inspiring culture and people practices.

You will report into our Chief People Officer and could be based in any of our office locations with an expectation of regular travel to our NY headquarters.


  • Develop an enterprise-wide, global learning strategy that spans in-person, virtual, 1:1, self-paced, and blended methodologies as well diverse content areas
  • Curate cutting edge learning solutions that align to Squarespace’s overall business objectives
  • Lead, coach, and develop a global team of Learning & Development professionals
  • Consult with business leaders, HR Business Partners, and the executive leadership team to identify learning needs; use these opportunities to set the team’s overall strategy and enable Squarespace’s continued growth
  • Work collaboratively across the organization to build a talent development strategy, internal mobility strategy, and succession planning strategy with the Vice President of People Programs and other team members
  • Design leadership development programs across all levels of leadership (including executive) to increase leadership effectiveness and support succession planning
  • Curate and maintain a new hire onboarding program that showcases Squarespace’s culture and sets new hires up for success in their roles
  • Identify, vet, and onboard vendors / offerings to supplement internal Learning & Development resources


  • 15+ years of experience in building and scaling Learning & Development programs for multiple organizations, with exposure to a variety of industries and approaches
  • Bachelor's Degree with a strong preference for an advanced degree or certification in Organizational Development, HR, or a related field
  • Excellent verbal and written communication skills
  • Able to package and present complex analyses and recommendations clearly
  • Ability to analyze and interpret data and leverage those insights into critical decisions
  • Extensive experience influencing and gaining buy-in from executive leadership 
  • Outstanding interpersonal, executive presence, and coaching skills required
  • Executive Coaching Certification preferred


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 900 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.

About Squarespace

Squarespace's platform empowers millions of people — from individuals and local artists to entrepreneurs shaping the world’s most iconic businesses — to share their stories and create an impactful, stylish, and easy-to-manage online presence.


Want to learn more about Squarespace? Visit Squarespace's website.