Senior People Operations Specialist (Contract)

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 commun