Senior People Operations Specialist (Contract)

Roofr; Canada; Hybrid; CAD 80,000 - 95,000; Full time

Benefits offered by this job

1st week PTO

Friday off per month

Company-wide shutdown for holidays

Flexible time off

Tuition/benefits support

Parental leave

Learning & development opportunities

Home office stipend

Internet/phone allowance

Remote first culture

Weekly paydays

Job summary

Roofr is seeking a Senior People Operations Specialist for a 12-month contract to lead onboarding, engagement, and benefits coordination for a remote Canada-wide team. You will partner with senior People Ops leadership to scale HR processes and ensure a human-centered employee experience across the lifecycle.

The role focuses on policy maintenance, HRIS data integrity in Rippling, and cross-border employment management via Deel, enabling effective people operations at scale.

Qualifications

• 3–5 years of experience in People Operations or HR Coordination, preferably in remote startups.
• Experience partnering with managers on performance, org design, and workforce planning.
• Strong communication, empathy, and relationship-building across teams.
• Comfort with HRIS, benefits, and policy documentation.

Responsibilities

• Act as trusted advisor to teams on performance, org design, and people strategy.
• Support onboarding, engagement, benefits coordination, and leave tracking.
• Maintain and audit employee data in HRIS (Rippling) and generate reports.
• Document and communicate People policies and resources across the organization.
• Support leadership development and coaching resources for managers.

Skills

People Operations

HR Coordination

HR Business Partner

Communication skills

Problem solving

Tools

Rippling

Deel

Job description

Senior People Operations Specialist (Contract)

Remote - Canada

At Roofr, we’re obsessed with our customers. We constantly gather feedback to shape, prioritize, and launch the products they truly need. That’s what makes Roofr’s CRM special. We started by building essential sales tools like aerial roof measurements and digital sales proposals. But when our customers asked for a simple, affordable way to manage and scale their entire businesses, we listened. So, we created a CRM that connects these solutions—along with payments, material ordering, and more—into a seamless, powerful platform. With a clear roadmap ahead, we’re excited to continue expanding and leading the market with innovative products.

We have an amazing culture, strong financials, and best-in-class company metrics. It’s an exciting time to be part of an extraordinary startup that is already successful, yet still early enough to offer its team significant growth, equity, and the opportunity to make a real impact.

This position is for an existing vacancy.

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

What You’ll Bring to the Role

• Bring 3–5 years of experience in People Operations or HR Coordination, ideally at a scaling, remote startup environment of similar size (150-300 employees).
• Have high energy, high empathy and a clear culture champion- You create a welcoming and collaborative community environment. You have an amazing attitude, you are personable, approachable, and always eager to help.
• Have experience working as an HR Business Partner, partnering directly with managers and teams on employee relations, performance, organizational changes, and other people-related matters.
• Are a Creative Problem Solver- You think outside of the box to come up with novel ideas and approaches to situations working around the system as needed.
• Are Resourceful- You thrive in a dynamic environment where new challenges are the order of the day. You are constantly thinking about how to do x,y or z faster and smarter.
• Communicate clearly and effectively - You know how to read an audience and are able to customize your communication to make that audience want to listen. Your messages have a crystal clear focus. Concise yet tactful. Simplifier, not a complicator.
• Have the ability to prioritize - Highly effective keeping track of relative priorities and shifting things around as needed to fulfill overall strategy. You push things back when necessary, stay calm under pressure and try out new techniques to improve your work and quickly come up with solutions, when problems arise. Able to triage and resolve problems. Proactive. Take ownership.
• Have a sharp eye for detail and a high bar for quality- You have the highest standards and won’t rest until a job is done properly. You are organized and know exactly what needs to happen to complete a task correctly. Detail oriented. Prioritizer. Manage multi-priorities w/o crumbling. Process maven.

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. While many hires fall within the beginning to midpoint of the band to allow for growth over time, we tailor offers based on each candidate’s experience, seniority, and demonstrated impact.

What we offer (US + Canada)

When you join our team, you’re not just accepting a job. You’re making a career move. Here’s how we’ll support you in doing some of the most impactful work of your career:

• 1st week of employment is mandatory PTO! Start your journey with Roofr by decompressing and recharging - we will see you in week 2!
• 1 Friday off per month (we call those our 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
• Generous Parental Leave policy
• We host an annual company retreat with great team building activities
• Ample learning and development opportunities to continue growing your career
• Home office setup stipend
• Internet and phone allowance
• Remote first culture
• Weekly Friday paydays!

At Roofr, we’re big fans of AI. It helps us write job descriptions that don’t put you to sleep, takes notes during interviews so we can actually listen, and even helps us track down awesome humans like you.

Feel free to use AI to prep, research, or get pumped up for your interview (we see you, ChatGPT power users). But when it’s time to chat, we’d love to meet you, not your AI alter ego. Bring your real, unfiltered self, we promise we will too.

And don’t worry, a real, live human is behind every part of our process. Every application is reviewed by a real person, and you’ll always speak with real humans throughout the interview process. No bots, just good people.

Roofr is proud to be an equal opportunity employer. We are committed to equal employment opportunity in the workplace regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status.