People Operations Generalist

About the Role

We're looking for an experienced People Operations Generalist based in North America to build and run the people function at Pragma. This is a hands-on, full-stack People role: you'll own the day-to-day of how we hire, level, pay, develop, and support our team across the US and internationally. You are AI-native and have built automations and systems to enable your job and company. You'll partner directly with the founders, leadership, and Finance to keep Pragma a place where great people want to do their best work. If you're energized by owning the full breadth of People - from an employment letter, to a compensation cycle, to a company offsite - and you want the autonomy to run, this is the role.

What You'll Do

People Partnering & Employee Relations

• Serve as the people point of contact for day-to-day people questions and general employee conversations
• Support managers and leadership through team changes, reorganizations, and evolving headcount needs
• Handle sensitive people matters - performance concerns, conflict, and terminations - with discretion and sound judgment

Recruiting & Contracts

• Run recruiting end-to-end: sourcing, interview coordination, and managing candidates through to offer
• Draft and manage employment documentation for both FTEs and contractors - offer letters, employment agreements, and contractor agreements
• Design and continuously improve onboarding so new hires ramp quickly, and run a smooth, well-documented offboarding process

Performance & Development

• Run Pragma's annual and mid-year performance review cycles end-to-end
• Build and maintain manager toolkits and enablement so managers can give effective feedback and run reviews well
• Own and maintain the company's leveling framework and career ladders

Compensation, Leveling & Equity

• Partner with Finance on company-wide compensation - benchmarking, banding, and running comp cycles
• Co-manage variable compensation plans for the Sales and Creators teams
• Partner with Finance on equity refreshers and broader equity administration
• Manage leveling and compensation approach as the company scales

Payroll, Benefits & Compliance

• Run payroll for both employees and contractors, and manage the vendor stack (e.g., Rippling, Bennie, Betterment, Sterling, Common Wealth)
• Administer benefits and 401(k), including open enrollment
• Manage Employer of Record (EOR) relationships and make country-specific decisions on benefits for international team members and contractors
• Own immigration and relocation (immigration/emigration) matters, coordinating with counsel where needed
• Keep Pragma compliant with employment law across the jurisdictions where we operate

People Operations & Offsites

• Plan and execute company-wide and sub-team offsites - logistics, budget, and programming
• Build the lightweight systems, documentation, and tooling that keep People operations running smoothly

Requirements

Experience

• 3-7 years in People Operations, HR, or a People Partner / HR generalist role
• Experience at a startup or high-growth technology company, ideally as an early or first dedicated People hire
• Hands-on experience across the full People stack - recruiting, compensation, benefits, payroll, and employee relations
• Track record of building People processes from scratch, not just administering existing ones
• Experience supporting distributed and international teams a strong plus

Skills

• Fluency with compensation and leveling - banding, benchmarking, variable comp, and equity basics (comfort with tools like Pave a plus)
• Comfortable owning sensitive conversations and situations with empathy, discretion, and good judgment
• Highly organized and detail-oriented - you can run a comp cycle and a review cycle in parallel without dropping either
• Familiarity with modern People tooling (e.g., Bennie, Sterling, Common Wealth, and EOR providers)
• Self-starter who's comfortable building process and operating with autonomy
• Excellent communication skills across all levels of the organization

Location & Logistics

• Based in North America
• Willingness to travel occasionally for offsites and team gatherings
• Remote-first with occasional team gatherings
• Apply at (alt contact: careers@pragma.gg)