Manager, People Operations

Remote (Canada) | Full-time, US Eastern Hours

CAD $95,000 - $135,000 (approximately $67,000-$96,000 USD)

Position Overview

The Manager, People Operations will build and run the operational backbone of the employee experience across ANNA's US markets - onboarding workflows, payroll accuracy, multi-state compliance, employee relations, performance infrastructure, and workforce reporting.

This is a high-velocity build role with unusually broad ownership for a manager-level position. We are scaling across states, which means the compliance calendar, the policy library, the dashboards, and the ER processes largely remain to be created - you will create them, run them, and improve them simultaneously. This is deliberately a sleeves-rolled-up role: you'll be in the payroll run, the I-9 file, and the compliance tracker yourself, and that's by design. You'll own US employment infrastructure end to end from Canada: state registrations, payroll cycles in Rippling, credential and I-9 compliance for a frontline clinical workforce, and the leave-law and classification decisions that keep a multi-state healthcare employer clean.

ANNA is an AI-native company, and we expect People Operations to be built that way - AI-assisted policy drafting, automated compliance monitoring, agentic onboarding workflows. You'll build people systems that most HR teams twice our size are still waiting on.

Strong performance in this seat has a defined growth path to Senior Manager, People Operations.
What This Role Is Really Like

• Builder-first. You'll create most systems from scratch. The satisfaction here is in standing things up.
• High-throughput. Payroll runs, compliance deadlines, ER cases, onboarding cohorts, and executive reporting all move on their own clocks. Strong operators find the rhythm; this role rewards them.
• AI-leveraged. The only way one person runs this scope is with AI doing the heavy lifting - and you'll build and improve those workflows yourself.
• High-agency. You'll spot the compliance gap or process failure before anyone assigns it to you - and fix it.
• Precise at volume. I-9s, credential expirations, deduction accuracy - the work is recurring and consequential, and the standard is zero dropped balls.

Key Responsibilities & Deliverables

Payroll & HRIS Operations

• Own end-to-end US payroll execution in Rippling across multiple states, including deductions, adjustments, and off-cycle runs, with a zero-defect standard
• Serve as system owner for the HRIS - configuration, workflow automation, data integrity, and integrations with ANNA's broader stack
• Manage benefits administration operations in partnership with brokers and carriers

Compliance & Risk

• Build and run the multi-state compliance calendar: state registrations, wage and hour requirements, leave laws, posting requirements, and healthcare-specific credentialing
• Own I-9 and work-authorization compliance and the credential-expiration monitoring system for clinical staff
• Maintain the policy library and employee handbook across states, using AI-assisted drafting and review

Onboarding & Employee Lifecycle

• Design and run onboarding workflows that get new clinical and corporate hires productive fast - measured in hours, with automation carrying the repetitive load
• Own offboarding, transfers, and lifecycle changes with clean documentation and system hygiene

Employee Relations & Performance Infrastructure

• Run ER casework end to end under US employment law - documentation, investigation support, performance improvement plans, and terminations - in partnership with leadership
• Build ANNA's performance management infrastructure: review cycles, calibration tooling, and the reporting behind them

Reporting & AI-Native Systems

• Build and maintain workforce dashboards leadership actually uses: headcount, retention, compliance status, payroll accuracy
• Continuously identify manual People processes and replace them with AI-powered or automated workflows you design yourself

Qualifications

Required

• 4-6+ years in People Operations or HR operations, including time as an early People hire at a high-growth startup or scale-up
• Hands-on ownership of US employment infrastructure: multi-state payroll, state registrations, I-9 compliance, FLSA classification, and leave-law administration
• Experience personally running US ER cases end to end, including documentation and difficult conversations
• Demonstrated AI fluency through real work product - automated workflows, AI-assisted documentation systems, or reporting builds you created yourself
• Ability to work US Eastern business hours
• Precision and follow-through at high volume

Preferred

• Rippling administration experience
• Experience supporting a frontline, multi-site, or healthcare workforce (shift schedules, credential tracking, high-volume hiring)
• Background at an EOR, PEO, or payroll provider serving US clients
• Experience implementing or migrating an HRIS or payroll platform yourself

If you don't meet every preferred qualification, we still encourage you to apply.
Ideal Candidate

You are a precision-obsessed builder who thrives where systems remain to be created. You started somewhere structured - a payroll bureau, an EOR, people advisory - and it gave you zero-defect instincts; then you joined a scale-up as one of the first People hires and discovered you love standing things up at speed. You talk about your work in artifacts and numbers: the compliance calendar you built, the payroll migration you ran solo, the error rate you drove to zero. You use AI as a genuine work multiplier and have the workflows to prove it. You are energized by ownership well beyond a typical manager-level scope, and you're motivated by the chance to build the people engine of a mission-driven healthcare company from the ground up.

Compensation & Benefits

Base Compensation

CAD $95,000 - $135,000

Bonus

Target 10-15% of base

Engagement Structure

Full-time engagement through a Contractor of Record in Canada

Additional

Paid time off and holidays; professional development and growth opportunities; supportive leadership and collaborative team culture

Remote, Canada-based, full-time US Eastern hours.