Senior People Operations Specialist

About the role

The Senior People Operations Specialist at Iterative Health is a critical individual contributor responsible for helping scale and optimize the infrastructure that supports the employee experience.

Responsibilities

• Administer employee benefit programs, including medical, dental, vision, life insurance, disability, retirement, wellness, and voluntary benefits.
• Serve as the primary point of contact for employee benefits inquiries and issue resolution.
• Manage benefit enrollments, qualifying life events, terminations, and annual open enrollment processes, partnering with brokers, vendors, and HRIS providers to ensure accuracy and a seamless employee experience.
• Partner with brokers, vendors, and internal stakeholders to support benefit administration, audits, benchmarking, vendor evaluations, and program enhancements.
• Support the leave process, partner with third-party leave administrators, HR Business Partners, managers, and payroll to support leave administration, ensure compliance, and maintain accurate documentation and records.
• Support onboarding and offboarding processes, ensuring accurate employee communications and coordination with payroll, finance, and external vendors.
• Develop and maintain process documentation, data governance standards, and system procedures.
• Maintain employee records, including I-9s, licenses, certifications, and other required documentation.
• Support additional People Team projects and initiatives as assigned.

Requirements

• 5+ years of experience in benefits administration, HRIS management, leave administration, or People Operations.
• Strong knowledge of employee benefits programs, retirement administration, and leave management.
• Experience administering FMLA, ADA, COBRA, disability, and state leave programs.
• Experience working within HRIS platforms and managing employee data and workflows from ADP, Rippling, UKG, and/or Paylocity.
• Strong organizational skills with exceptional attention to detail and follow-through.
• Ability to manage multiple priorities and work independently in a fast-paced environment.
• Strong communication and interpersonal skills with a service-oriented mindset.
• Ability to handle sensitive and confidential information with professionalism and discretion.
• Proactive, solutions-oriented, and process improvement focused approach.

Qualifications

• Proven ability to build, improve, and modernize People Operations processes in a high-growth environment.
• Experience with HR technology, AI, and analytics tools to improve reporting capabilities, identify trends, and support data-driven decision-making.
• Experience with regulatory compliance and reporting, including EEO-1 reporting, unemployment claims, workers' compensation, compensation reporting, and other required filings.
• Experience with process optimization, automation, and AI-enabled solutions.

Skills

• Expertise in employee benefits programs, retirement administration, and leave management.
• Strong organizational and analytical skills.
• Excellent communication and interpersonal skills.
• Experience with HRIS platforms and leave administration.
• Knowledge of regulatory compliance and reporting requirements.
• Ability to manage multiple priorities and work independently in a fast-paced environment.
• Experience with process optimization, automation, and AI-enabled solutions.

Benefits

• Hybrid work environment with in-office collaboration two days per week in either our NYC or Boston office.
• Comprehensive medical, dental, and vision coverage, with up to 80% of premiums covered by Iterative Health.
• Mental health and wellness support through Spring Health.
• Health HSA or FSA options, and commuter FSA contributions supported by Iterative Health.
• Unlimited PTO, 12 company holidays, and a company-wide shutdown between Christmas and New Years.
• 401(k) program with a company match of up to 3% (up to $3,000 annually).
• Weekly in-office lunch benefit every Tuesday.
• 100% company-paid short-term and long-term disability coverage.
• Annual wellness and professional development stipend to support your health and growth.

Pay

New York pay range: $90,000 USD - $130,000 USD

Schedule

Flexible schedule to accommodate hybrid work environment.