People Operations Manager - Tremendous

Tremendous is the global platform built for businesses to send thousands of payouts to anyone, anywhere, for free. We're trusted by 20,000 organizations like Atlassian, MIT, and United Way to deliver gift cards and money to millions of recipients worldwide.

We're profitable and growing without outside investors. We're a fully remote, high-documentation, low-meeting culture, which means more time for what matters in both your professional and personal life. The team agrees– our employee NPS is in the high 80s.

About the Role

We're ~175 people across the US, Canada, the UK, Brazil, and elsewhere, and we're launching our first dedicated people function. You'll own people operations end to end, be the go-to person when something is wrong, and run our immigration program in conjunction with outside counsel.

What You'll Do

• Own our HRIS and associated systems.
• Administer benefits for US, Canadian, and international employees: open enrollment, carrier and broker escalations, HSA and FSA, COBRA, 401(k), and required annual notices.
• Own the employee handbook, HR wiki, and people policies, writing any missing policies.
• Manage onboarding end to end (cohort logistics, new hire paperwork, first-90-days experience) and offboarding (exit interviews, severance logistics).
• Serve as the company's HR point of contact. Take reports, run investigations, and write up findings while building a low-risk reporting process.
• Run our biannual HR cycle (performance check-ins, compensation review, employee engagement survey) on schedule and improve it each time.
• Handle off-cycle compensation changes, promotions, relocations, international moves, and related compensation implications.
• Partner with recruiting on international employment models (EOR, contractor).
• Own our immigration program: manage active O-1, L-1A, H-1B, and PERM matters end to end, drive outside counsel timelines, track renewals, and own I-9 compliance.

What We're Looking For

• Excellent judgment in situations with no precedent, with the ability to write down your reasoning.
• Absolute discretion and the ability to build trust quickly.
• Proactive mindset: you'd rather build the tracker than field the emergency.
• Comfort being senior while still executing unglamorous administrative work.
• Clear written communication for documentation-first policies, summaries, and company-wide communications.

What You'll Bring

• 5+ years in people operations, HR, or a people partner role, including time at a company without a large HR team.
• Experience independently running workplace investigations, including harassment matters, and writing defensible documentation.
• Deep experience administering US benefits and leave (global benefits experience is a bonus).
• Strong HRIS experience (Rippling preferred).
• Direct, hands-on experience with employment-based immigration: H-1B, O-1, L-1, and PERM.
• Experience running performance and compensation cycles for 100+ people.

What's Cool About the Role

• First Hire: Define what the people function is here with direct access to leadership and real latitude.
• Competitive Pay & Equity: Base salary range of $110k to $160k plus equity.
• Real Benefits: 100% covered health (US), unlimited PTO, and 12-16 weeks paid parental leave.
• Fully Remote: Work from anywhere in the Americas.
• Great Culture: Read more about how we work in our public handbook.