Head of People Operations (HR) at Tremendous

Tremendous is the global platform trusted by 20,000+ organizations, including Atlassian, MIT, and United Way, to send thousands of payouts worldwide for free. Their fully remote, low-meeting culture fosters high employee satisfaction with an NPS in the high 80s.

About the Role

As the first dedicated People Operations lead at Tremendous, you’ll own the entire function end-to-end. This includes being the primary point of contact for employees, managing HRIS systems, and overseeing the immigration program in collaboration with external counsel. The team spans 175+ employees across the US, Canada, UK, Brazil, and beyond.

What You’ll Do

• Own and administer HRIS systems and associated tools.
• Handle US, Canadian, and international benefits, including open enrollment, HSA/FSA, COBRA, 401(k), and required annual notices.
• Develop and maintain the employee handbook, HR wiki, and company policies.
• Oversee onboarding and offboarding, including cohort logistics, new hire paperwork, and exit interviews.
• Serve as the HR point of contact, investigating reports, conducting workplace investigations (including harassment matters), and documenting findings.
• Run biannual HR cycles, including performance check-ins, compensation reviews, and employee engagement surveys.
• Manage off-cycle compensation changes, promotions, relocations, and international moves.
• Partner with recruiting on international employment models (EOR, contractor).
• Lead the immigration program, managing active O-1, L-1A, H-1B, and PERM matters, tracking renewals, and ensuring I-9 compliance.

What We’re Looking For

• Proven ability to make judgment calls in ambiguous situations and document reasoning clearly.
• Quickly earns trust and confidentiality from employees and stakeholders.
• Proactive mindset—prefers building systems to handling emergencies.
• Comfortable balancing senior leadership with unglamorous administrative tasks (e.g., open enrollment, I-9 signatures).
• Excellent written communication skills for policies, investigations, and company-wide comms.

What You’ll Bring

• 5+ years in People Operations, HR, or People Partner roles, including experience at a company without a large HR team.
• Direct experience independently running workplace investigations, including harassment matters, with defensible documentation.
• Deep experience administering US benefits and leave policies; global benefits experience is a plus.
• Strong HRIS experience, preferably with Rippling.
• Hands-on experience with employment-based immigration (H-1B, O-1, L-1, PERM).
• Proven track record of running performance and compensation cycles for 100+ employees.

What’s Cool About the Role

• You’ll define the people function from the ground up with direct access to leadership and full autonomy.
• Competitive pay and equity: Base salary range is $110k to $160k.
• 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: Explore their public handbook for more details.