Senior Benefits Operations Specialist

Remote - U.S. & Canada Only | Full-Time | $65,000-$80,000 USD

We're not hiring aPeople Ops Specialist to "keep the inbox clean." We're hiring a builder—someone who owns U.S. benefits end-to-end, spots what's missing before anyone asks, and makes the system better every month.

Level Agency is looking for a mid-senior People Operations Specialist with deep expertise in U.S. benefits administration. You'll be the operational engine behind our Medical, Dental, Vision, Retirement, Life, Disability, Pet insurance, and perk programs—partnering closely with Payroll to ensure deductions are accurate and compliant, and ensuring our benefits experience is smooth, clear, and employee-first.

We'll prioritize candidates who have supported benefits in Canada and/or Mexico, but this role is primarily focused on the U.S.

This role isn't for everyone.

You'll thrive here if:

• You can run benefits without being micromanaged
• You see broken workflows and fix them (instead of tolerating them)
• You're comfortable interpreting state-specific rules and translating them into clean processes
• You have strong judgment, high follow-through, and a "figure it out" mindset
  
  

You'll struggle here if:

• You need a checklist from someone else to get started
• You avoid ambiguity or ownership
• You rely on vendors/brokers to do the thinking for you
  
  

About Level Agency

We're an AI-powered performance marketing agency—built for precision, designed to scale, and powered by a scientific mindset. At Level, we blend strategy, media, creative, and machine intelligence to deliver outcomes that matter. Every time. At scale.

We've been named one of Pittsburgh's Best Places to Work and an Inc. 500 Fastest-Growing Company. Our team is fully remote, deeply collaborative, and relentlessly driven.

Your Role (and Impact)

As our People Operations Specialist (Benefits-Focused), you'll own the day-to-day administration and continuous improvement of our U.S. benefits and perks programs.

You will:

• Administer U.S. benefits programs end-to-end: Medical, Dental, Vision, 401(k)/Retirement, Life Insurance, Short-Term Disability, Long-Term Disability, Pet insurance, and more.
• Own benefits lifecycle events: new hire enrollments, qualifying life events, terminations, and annual open enrollment
• Partner tightly with Payroll to set up and maintain accurate deductions in the payroll processor, troubleshoot discrepancies, and ensure clean reconciliations
• Manage ongoing vendor/broker coordination and serve as a reliable point of contact for escalations and issue resolution
• Ensure benefits practices and administration align with U.S. federal and state requirements (and help identify when we need external guidance)
• Support people programs and perks administration like PTO processes, WFH stipends, and other employee experience initiatives
• Maintain strong documentation: SOPs, employee-facing guides, and internal workflows that make benefits "easy to navigate"
• Identify gaps, propose improvements, and implement changes—without waiting for permission
  
  

Bonus / Priority:

• Experience supporting benefits administration in Canada and/or Mexico (in addition to U.S.)
  
  

Requirements

You Bring:

• 4-8+ years of People Operations / HR Generalist experience with significant U.S. benefits ownership
• Hands-on administration experience across core U.S. benefits (Medical/Dental/Vision/401k/Life/STD/LTD)
• Proven experience collaborating with Payroll on deductions, audits, reconciliations, and issue resolution
• Strong working knowledge of U.S. benefits compliance basics and state-by-state nuances (and the confidence to research what you don't know)
• A self-starter mindset: you proactively find what needs attention and follow through to completion
• High integrity and discretion when handling sensitive employee data
  
  

Preferred Experience:

• Benefits exposure in Canada and/or Mexico
• Experience supporting a distributed/remote workforce across multiple states
• Familiarity with benefits renewal cycles, broker relationships, and open enrollment project management
  
  

AI Expectations

At Level, proficiency with AI tools is a core part of your role—not a nice-to-have. Your success depends not only on your functional expertise, but also on your ability to actively integrate AI into how you work.

You are expected to:

• Use tools like ChatGPT (and others) to improve documentation, employee FAQs, process mapping, and operational efficiency
• Share prompts, workflows, and learnings to elevate the broader team
• Treat AI as a force multiplier for clarity and speed—not a crutch
  
  

Our Core Values

• No Ego, All In: We don't do "that's not my job." We win together
• Better Every Day: We want the feedback—even when it stings
• Relentless for Results: Activity is nothing without outcomes
• Driven by Truth: We challenge assumptions and follow the data
  
  

Benefits

Perks & Benefits include (may vary by location):

• Competitive salary based on experience $65,000 - $80,000 USD
• Remote work (U.S.-based)
• Unlimited PTO
• 12 weeks Paid Parental Leave
• 8 weeks Paid Family Leave
• 12 Paid Holidays + 2 Floating Holidays
• Summer Fridays
• Competitive Medical Plan Options
• 100% Employer-Paid Vision & Dental Insurance
• Pet Insurance
• 401(k) with 3% Employer Contribution (100% vested)
• $100 Monthly WFH Stipend (paid quarterly)
• EAP + Concierge Support Services
• In-person & virtual company events
• Peer-to-peer recognition programs
  
  

Remote-First

This is a remote role open to candidates located within the U.S. We are unable to sponsor visas at this time.

Level Is Built on Inclusion

We are committed to Diversity, Equity, Inclusion, and Belonging (DEIB). Level is proud to be an Equal Opportunity Employer. We prohibit discrimination and harassment of any kind and celebrate what makes you, you—regardless of race, gender identity, age, disability status, sexual orientation, or background.

Ready to Apply?

Click below and submit your resume. You'll also be asked a few thoughtful questions—take your time. We care more about your thinking than your pedigree.

Let's build something together.