Senior Benefits Manager

Title: Senior Benefits Manager (Contract)

Location: United States

Type: Contract

Workplace: remote

Category: People/Recruiting


Attentive is the AI marketing platform for leading brands, designed to optimize message performance through 1:1 SMS and email interactions. Infusing intelligence at every stage of the consumer’s purchasing journey, Attentive empowers businesses to achieve hyper-personalized communication with their customers on a large scale. Leveraging AI-powered tools, a mobile-first approach, two-way conversations, and enterprise-grade technology, Attentive drives billions in online revenue for brands around the globe. Trusted by over 8,000 leading brands such as CB2, Urban Outfitters, GUESS, Dickeys Barbecue Pit, and Wyndham Resort, Attentive is the go-to solution for delivering powerful commerce experiences for consumers with the brands they love.

Attentives growth has been recognized by Deloittes Fast 500, Linkedins Top Startups and Forbes Cloud 100 all thanks to the hard work from our global employees!

Who we are

We are looking for a Senior Benefits Contractor with strong technical expertise for a 6-7 month engagement with the Total Rewards Team. Primary responsibilities are to keep benefits on track and moving in a good direction, build out and plan for US Open Enrollment scheduled for the fall of 2024, respond to employee inquiries, and manage vendor relationships with providers. Reporting to our Director of Compensation & Benefits, this person will lead the administration of all our benefits programs and drive benefit communications.


  • Administer all global employee benefits programs such as medical, dental, vision plans, ancillary plans, and 401(k) plan
  • Administer perk programs and ensure they are market-competitive and easily
  • accessible
  • Plan and lead the annual Open Enrollment process, including communicating
  • new plans or changes to existing plans, preparing plan summaries, obtaining
  • all marketing documents, ensuring the open enrollment portal is configured,
  • payroll deductions are set, and integrations with vendors are enabled.
  • Manage relationships with benefits broker and all benefit vendors.
  • Monitoring vendor performance, ensuring programs are cost-effective and meeting service level agreements
  • Manage Wellness Funds
  • Ensure company compliance with federal, state, and local laws, including
  • required notice distribution (ERISA, SARs, CMS, etc) non-discrimination
  • testing, ACA reporting, 5500 CMS, HIRD, and PCORI filing and ensuring
  • reporting requirements are met timely
  • Audits of benefits plans, deductions, and bills.
  • Partner with Payroll to operationalize deductions and any related issues on
  • both health/welfare and 401(k) plans
  • Manage Leave of Absence Process and Claims
  • Answer all employee benefits questions via email and the helpdesk ticketing
  • system
  • Suggest and implement wellness programs and initiatives
  • Partner with Finance on invoicing and budgeting
  • Own Internal Wiki Page Creations and keeping them up to date
  • Lead Weekly/Monthly provider and broker calls

Requires Skills & Experience

  • Bachelors degree or relevant experience
  • 10+ years of experience working in benefits
  • In-depth experience leading and managing benefits, including medical,
  • dental, vision, ancillary products, perks, wellness programs, 401(k), and LOAs
  • Prior experience in the technology industry, primarily in SaaS Companies
  • Advanced Excel/Google Sheets skills (Vlookups, Pivot Tables, Dynamic Sheets)
  • Ability to work with a sense of urgency in a dynamic environment
  • Ability to be solutions-oriented and, when problems arise, have a clear proposal for moving forward
  • Knowledge of EDIs
  • ADP Workforce Now Experience a plus
  • Benefit Experience in the UK and Australia a plus
  • Experience Working with Self Funded Plans a plus

Job Classifications

  • 40 Hours Per Week
  • Engagement Period 6 Months
  • Benefit Ineligible
  • Fully Remote / 0% Travel

Preferred Technology Experience

  • HRIS & Payroll Systems – ADP Workforce Now
  • Benefit Portals – Fidelity, Guardian, Lincoln, Cigna, Navia, and Kaiser
  • Internal Tools & Help Desks – Jira & Confluence
  • Microsoft Suite (Word & Excel)
  • Google Suite (Mail, Drive, Sheets, Docs, & Slides)
  • Adobe Acrobat Pro


Attentive Company Values

Default to Action – Move swiftly and with purpose

Be One Unstoppable Team – Rally as each others champions

Champion the Customer – Our success is defined by our customers’ success

Act Like an Owner– Take responsibility for Attentives success

Learn more about AWAKE, Attentives collective of employee resource groups.

If you do not meet all the requirements listed here, we still encourage you to apply! No job description is perfect, and we may also have another opportunity that closely matches your skills and experience.

At Attentive, we know that our Company’s strength lies in the diversity of our employees. Attentive is an Equal Opportunity Employer and we welcome applicants from all backgrounds. Our policy is to provide equal employment opportunities for all employees, applicants and covered individuals regardless of protected characteristics. We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation.