Senior People Operations Specialist

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.

We’re looking for a thoughtful, proactive, and detail-oriented Senior People Operations Specialist to join our growing team. 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. People Ops Manager, People Ops Specialist, and VP of People & Talent to support and scale critical operational processes across the entire employee lifecycle.

What you get to do:

• 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.
• 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 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. 
• 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.

🏠 What we offer:

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:

🏝️ Vacation/Paid Time Off:

• 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 
• RRSP/401k match
• Generous Parental Leave policy

🤝 Perks:

• We host 2 retreats per year and 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!

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.

IMPORTANT NOTICE: Our company takes the security and privacy of job applicants very seriously. We will never ask for payment, bank details, or personal financial information as part of the application process. All our legitimate job postings can be found on our official career site (https://boards.greenhouse.io/roofr). Please be cautious of job offers that come from non-company email addresses (@roofr.com), instant messaging platforms, or unsolicited calls.