[Hiring] Senior People Operations Specialist @Roofr

Role Description

We’re looking for a thoughtful, proactive, and detail-oriented Senior People Operations Specialist to join our growing team on a 12-month contract. You’ll help build and support key programs across the employee experience—onboarding, engagement, performance, benefits, and more—ensuring our team has the tools, resources, and support to thrive.

This is a great opportunity for someone who’s passionate about people, thrives in a fast-paced, fully remote startup environment, and isn’t afraid to roll up their sleeves to get things done.

You’ll work closely with our Sr. Manager, People Ops, People Ops Specialist, and SVP of People & Talent to support and scale critical operational processes across the entire employee lifecycle.

What You’ll Get to Do

• People Business Partnering: Serve as a trusted advisor to specific teams or business units by supporting managers on performance, org design, workforce planning, and people strategy to drive team effectiveness.
• Employee Support & Relations: Be a go-to resource for employees across the org—answering questions, providing support, and helping solve day-to-day people-related issues with empathy and discretion.
• Onboarding & Offboarding: Ensure seamless onboarding experiences for new hires, including systems setup, orientation, and check-ins. Help coordinate offboarding processes with care and clarity.
• Benefits & Leave Coordination: Support benefits administration, employee leave tracking, and communication—partnering with US and Canadian brokers and internal stakeholders to ensure timely and accurate updates.
• HRIS & People Systems: Maintain and update employee data in our HRIS (Rippling), ensure data integrity, and support reporting needs for compliance and planning.
• Policy Support & Documentation: Help document and maintain our People policies and resources (handbooks, guides, processes), and ensure they're clearly communicated to employees.
• Employee Engagement & Culture: Support company-wide engagement efforts—from surveys to events—while bringing creativity and care to everything we do.
• Leadership Development: Support the growth of people managers and emerging leaders through coaching resources, development programs, and tools that build management capability across the org.
• Manage international employment via Deel, including onboarding, offboarding, compliance, and payroll coordination.
• Proactively identify opportunities to improve the employee experience and make our internal operations more efficient and human-centered.

Qualifications

• 3–5 years of experience in People Operations or HR Coordination, ideally at a scaling, remote startup environment of similar size (150-300 employees).
• High energy, high empathy, and a clear culture champion.
• Experience working as an HR Business Partner, partnering directly with managers and teams on employee relations, performance, organizational changes, and other people-related matters.
• Creative Problem Solver - Think outside of the box to come up with novel ideas and approaches to situations.
• Resourceful - Thrive in a dynamic environment where new challenges are the order of the day.
• Communicate clearly and effectively - Customize your communication to engage your audience.
• Ability to prioritize - Keep track of relative priorities and shift as needed to fulfill overall strategy.
• Sharp eye for detail and a high bar for quality - Organized and know exactly what needs to happen to complete a task correctly.

Compensation

Compensation Band: $80,000.00 - $95,000.00 CAD. Our compensation ranges are built using multiple market benchmarks and reflect both the scope of the role and current market data.

Benefits

• 1st week of employment is mandatory PTO.
• 1 Friday off per month (laundry days).
• Company-wide paid shutdown for the week between Christmas and New Years.
• Flexible time off.
• 80% employer-paid benefits in the U.S. and 100% employer-paid premiums for Extended Healthcare and Dental in Canada.
• RRSP/401k match.
• Generous Parental Leave policy.

Perks

• Annual company retreat with great team building activities.
• Ample learning and development opportunities.
• Home office setup stipend.
• Internet and phone allowance.
• Remote first culture.
• Weekly Friday paydays!