New York City, NY

Senior Benefits Analyst at Squarespace

| New York City, NY
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Senior Benefits Analyst 

Squarespace's Total Rewards team is seeking a Senior Benefits Analyst who has a passion for all things benefits at a scaling organization while providing administration and support for all employee benefit plans, programs, and policies.  In this role, you will manage employee benefit inquiries, execute our benefit programs, manage compliance related needs, monitor benefit eligibility, and support all other ad-hoc projects. This individual should be excited by the opportunity to be very hands-on with everything from day-to-day administrative work to longer-term, large-scale benefits projects.

You will report to our Senior Manager, Global Benefits. We are open to remote candidates as long as you reside in an approved state (please see the application question).

All Squarespace employees are working remotely at this time. We are closely monitoring the status of COVID-19 as we continue our work to build a return-to-work plan that ensures a safe return to our offices and provides flexibility for our employees. 

You’ll Get To…

  • Manage the day-to-day benefits operations and programs, including administration of current employee benefits (e.g., medical, dental, vision; life insurance plans, disability programs, 401(k) retirement), leaves and accomodations 
  • Providing ongoing support for vendor management including by participating in regular status calls and strategic reviews, identifying areas for process improvement and assisting with implementation of new initiatives
  • Liaise directly with employees in connection with questions about benefit eligibility, programming, leave management and escalating to Senior Manager, Global Benefits where appropriate
  • Develop and maintain process documentation (including SOPs, policies, templates and communications) for all benefit and leave programs and provide recommendations for process improvement, where appropriate 
  • Partner with payroll to ensure accurate and timely processing of benefits deductions and provide recommendations for areas of efficiencies and improvement 
  • Ensure data integrity and accuracy of employee benefits information through audits and billing reconciliation liaising with AP and vendors as required
  • Coordinate and facilitate compliance related matters, in partnership with external vendors, including (but not limited to) completion of Form 5500s, ACA filings, annual audits, and non-discrimination testing 
  • Support the annual benefits Open Enrollment process, including partnering with vendors/brokers/consultants to manage employee communications, prepare benefit plan materials, coordinate timelines and address employee questions
  • Stay on top of competitive market trends, summarize employee insights regarding benefits usage, requests and programming and provide thoughtful recommendations to Senior Manager, Global Benefits regarding potential opportunities to enhance current offerings
  • Partner with internal stakeholders such as Payroll, People Operations, HR Business Partners, Recruiting, Legal, and Finance on renewals, benefit program implementations and other areas related to benefits administration
  • Perform other Benefits/HR ad hoc projects as needed

Who We’re Looking For...

  • 4+ years of Benefits Administration experience
  • Strong knowledge of federal and state regulations, filing and compliance requirements affecting employee benefits programs, including ERISA, COBRA, ACA, etc.
  • Ability to manage expectations of and relationships with various key stakeholders across multiple areas, including senior leaders 
  • Exceptional attention to detail, organizational and analytical skills 
  • Ability to work independently and prioritize in a fast paced, high-growth environment
  • Commitment to driving results, including taking ownership for administration and improvement of benefits processes and programs  
  • Excellent communication skills (interpersonal, presentation, writing)
  • Technical proficiency in one or more HR Information Systems (WD a PLUS!)
  • Strong Excel skills required (vlookup, pivot tables, large data audit compares)
  • Experience working in a global organization and/or within tech a plus!
Benefits & Perks
  • Health insurance with 100% premium covered for you and your dependent children
  • Fertility and adoption benefits
  • Retirement benefits with employer match
  • Flexible vacation & paid time off
  • Up to 20 weeks of paid family leave
  • Equity plan for all employees
  • Pre-tax commuter benefits
  • Education reimbursement
  • Employee donation match to community organizations
  • 7 Employee Resource Groups across locations
  • Dog-friendly workplace
  • Free lunch and snacks
  • Private rooftop       
About Squarespace

Squarespace is a leading all-in-one website building and ecommerce platform that enables millions to build a brand and transact with their customers in an impactful and beautiful online presence. Our suite of products enables anyone at any stage of their journey to manage their projects and businesses through websites, domains, ecommerce, marketing tools, and scheduling, along with tools for managing a social media presence with Unfold and hospitality business management via Tock. Squarespace democratizes access to best-in-class design, helping our customers in approximately 200 countries and territories maintain consistent branding across all digital touchpoints to stand out online. Our team of more than 1,400 is headquartered in downtown New York City, with offices in Dublin, Ireland, Portland, Oregon, Los Angeles, California and Chicago, Illinois. For more information, visit www.squarespace.com

Our Commitment 

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, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

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Technology we use

  • Engineering
    • C++Languages
    • GolangLanguages
    • JavaLanguages
    • JavascriptLanguages
    • KotlinLanguages
    • PHPLanguages
    • PythonLanguages
    • ScalaLanguages
    • SqlLanguages
    • SwiftLanguages
    • ReactLibraries
    • ReduxLibraries
    • AngularJSFrameworks
    • Backbone.jsFrameworks
    • Ember.jsFrameworks
    • HadoopFrameworks
    • SparkFrameworks
    • SpringFrameworks
    • HiveDatabases
    • MongoDBDatabases
    • MySQLDatabases
    • PostgreSQLDatabases
    • RedshiftDatabases
    • KafkaDatabases
    • PrestoDatabases

What are Squarespace Perks + Benefits

Squarespace Benefits Overview

We take care of our employees in more ways than one. We offer competitive medical, dental, and vision for our employees and their dependents. We also offer up to 20 weeks of paid family leave (includes parental), daily gourmet lunches, and seasonal wellness programming, including meditation, yoga, and nutritionist sessions at the office. And so many snacks.

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Dedicated Diversity/Inclusion Staff
Highly diverse management team
Unconscious bias training
Diversity Employee Resource Groups
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Mental Health Benefits
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Match charitable contributions
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Adoption Assistance
Company sponsored family events
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Free Daily Meals
Game Room
Stocked Kitchen
Happy Hours
Pet Friendly
Recreational Clubs
Relocation Assistance
Home Office Stipend for Remote Employees
Professional Development Benefits
Job Training & Conferences
Tuition Reimbursement
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Continuing Education stipend
Time allotted for learning
Online course subscriptions available

An Insider's view of Squarespace

What does your typical day look like?

My days are usually split between weekly one-on-ones with my team and pockets of time where I can focus on what I need to get done for the week. The dedicated time to speak one on one with my team is the best place for me to hear about their wins, understand and coach them through their challenges, and help them move forward.


Technical Program Manager

How has your career grown since starting at the company?

I first stepped into Squarespace as an intern, and it’s been a crash course in all things advertising and design since then. I’ve worked on some cool projects, from developing a microsite built to celebrate our awesome customers called Makers & Dreamers to creating content for our product that tons of users will come across.


Art Director

What is your vision for the company?

My role is to lead the creation of a shared vision, strategy, and plan toward the development of a learning culture at Squarespace. We envision Squarespace becoming a place where people come to not just do their career’s best work, but also as a place where they learn and grow in unimaginable ways.


Director of Learning & Development

What does your typical day look like?

I’ve been measuring my time in weeks since I can’t make much progress in a single day. I am responsible for guiding my team in the right direction and am accountable for delivering high-quality projects on time. Monday is a meeting-free day. I use it to plan my week, focus on long-term planning, dig into problems and work on important tasks.


Engineering Manager

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