Head of Total Rewards

Squarespace, New York, NY

Help the world share their story

Squarespace is in search of a Director of Total Rewards to build and scale a total rewards strategy that will continue to attract the best and brightest as we enter our next phase of growth.  In this role, you will be responsible for designing and executing a total rewards strategy that will position Squarespace competitively in the market to attract, retain, and engage top talent. 

You will work collaboratively with the rest of the People Team and department leaders to build compensation and benefits programs to serve our rapidly growing global business. You’ll also work hand in hand with the broader People team leaders on projects and initiatives to cultivate our unique culture and people practices.

This role reports into our Chief People Officer and is based in New York.


  • Partner with the People leadership team and executives to define, develop, communicate and execute the total rewards strategy
  • Create a compelling and market competitive executive compensation strategy to ensure we’re attracting and retaining top leaders 
  • Develop a strong partnership with the HR Business Partner team and department leaders to consult and implement department specific reward and retention strategies aligned to Squarespace’s job architecture
  • Lead the overall compensation function including base, short-term and long-term incentive compensation; semi-annual compensation review cycle;  equity administration; market data survey participation
  • Lead the overall benefits function including the evaluation, recommendation, and implementation of changes and improvements to the benefits program; partner with vendors to manage the medical, dental, life, long-term and short-term disability insurance plans, flexible spending accounts and 401(k) plan; maintain benefit plan documents and summary plan description
  • Work with FP&A teams to accurately forecast spends for anything compensation and benefits related


  • 15+ years demonstrated experience in total rewards with at least 5 years in compensation at a high-growth technology company
  • BA/BS in Business Administration, MBA preferred
  • Progressive experience in executive compensation, base compensation, market pricing, variable pay, job evaluation/architecture, and cost modeling on a global scale
  • Global benefit experience including knowledge of health and wellness plans, time off practices, and retirement plans
  • A strong bias towards teamwork and ability to work in an ambiguous, fast paced, high growth, deadline oriented environment, while handling multiple projects and priorities simultaneously
  • Capability to handle confidential and sensitive information with discretion
  • Experience with vendor selection and RFPs
  • Strong communication skills (verbal, written and presentation)
  • Outstanding change management and communications skills



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 1000 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.