Senior Revenue 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. This position is for an existing vacancy. We’re looking for a Senior Revenue Operations Specialist to drive operational excellence, efficiency, and scalability across Roofr’s Revenue organization. As a key member of the RevOps team, you’ll play a hands-on role optimizing GTM processes, improving our technology ecosystem, strengthening data integrity, and building AI-ready systems that enable our Revenue teams to perform at their best. You’ll work closely with Sales, Marketing, Customer Success, and Enablement to identify operational challenges, develop solutions, automate manual processes, and ensure our systems and workflows support a seamless customer and revenue lifecycle. This is a highly collaborative, execution-oriented role for someone who enjoys solving complex operational problems, working deeply in systems and data, and turning business needs into scalable and AI-forward technology solutions. What You’ll Do: Optimize Revenue Processes & Systems • Identify operational challenges across the Revenue org and develop scalable solutions that improve efficiency, productivity, and the GTM experience. • Design, implement, and continuously optimize Revenue processes, workflows, and systems across the customer lifecycle. • Apply a structured, project-management-oriented approach to understand problems, evaluate solutions, manage implementation, and measure outcomes. • Partner with Revenue leaders and ICs to understand their needs, gather feedback, test solutions, and ensure initiatives meaningfully improve team performance. • Look for opportunities to simplify processes, eliminate unnecessary manual work, and design human-in-the-loop AI workflows to improve efficiency for Revenue teams. Drive Process Automation & AI Enablement • Identify opportunities to automate repetitive and manual processes using existing technology, integrations, and automation platforms. • Build and maintain workflows, automations, routing, notifications, and other system-based solutions that improve team productivity. • Leverage connectors such as Fivetran, Zapier, or similar platforms to connect systems and improve data flow. • Continuously evaluate opportunities to use AI and emerging technologies to improve Revenue productivity and operational scale. Own & Optimize the Revenue Technology Stack • Serve as a subject matter expert and administrator for HubSpot Marketing Hub and Sales Hub. • Own the creation, maintenance, and optimization of pipelines, workflows, custom views, templates, playbooks, lists, and other HubSpot functionality supporting Revenue initiatives. • Manage and optimize key Revenue technologies including Aircall, Sakari, Gong, Stripe, Hippo Video, and Guru. • Ensure systems are configured effectively, adopted appropriately, and integrated into Revenue workflows. • Stay current on product capabilities and emerging features, identify opportunities to improve our technology stack, and maintain relationships with key technology vendors. Strengthen Data & Revenue Insights • Maintain strong data integrity practices across the tools, processes, and automations you own. • Ensure GTM data is clean, consistently structured, and AI-ready. • Use data to identify trends, diagnose operational issues, and measure the impact of Revenue initiatives. • Support analysis related to lead scoring, customer health, pipeline performance, conversion, productivity, and other Revenue performance indicators. • Translate data and operational insights into actionable recommendations for Revenue teams. Partner Across Revenue • Work closely with leaders and ICs across Sales, Marketing, Customer Success, and Enablement to inform your roadmap and prioritize initiatives. • Partner with the Revenue Enablement Specialist to ensure new tools, processes, and AI-assisted workflows are effectively rolled out, documented, and adopted. • Engage Revenue team members as partners in testing new processes and tools, and incorporate their feedback into solutions. Documentation & Operational Excellence • Create and maintain clear documentation for tools, systems, processes, workflows, and automations. • Ensure documentation is accessible and easy for Revenue teams to understand and use. • Partner with Enablement to support training and adoption of new tools and processes. • Establish repeatable processes that make it easier for teams to understand and consistently use Revenue systems. What You’ll Bring: • 4+ years of experience in Revenue Operations, Sales Operations, Marketing Operations, or Customer Success Operations. • Hands-on HubSpot administration experience across Marketing Hub and Sales Hub. • Experience owning, implementing, and optimizing Revenue technology and GTM systems such as CRM, conversation intelligence, sales engagement, communication, customer education, and payment platforms. • Strong understanding of Revenue processes and how systems, data, and workflows support the broader GTM motion. • Experience building and optimizing workflows, automations, integrations, and data flows. • Strong analytical skills and the ability to use data to identify problems, inform decisions, and measure impact. • Demonstrated experience evaluating or implementing AI-powered GTM tools — not just familiarity, but hands-on work with AI-assisted workflows, automation platforms, or agentic tooling. • Strong project management skills with the ability to independently drive initiatives from concept through implementation. • Ability to thrive in a fast-paced, agile, and dynamic environment where priorities can change quickly. • Strong cross-functional collaboration skills and the ability to work effectively with stakeholders at all levels. • Excellent written and verbal communication skills, with the ability to translate technical concepts into clear, actionable recommendations. Who You Are: • You’re a builder and problem solver who enjoys figuring out how things work and finding better ways to make them work. • You naturally look for opportunities to simplify, automate, and scale processes and you think critically about where AI creates real leverage versus where humans still need to be in the loop. • You’re highly detail-oriented and understand that clean, well-structured data is the foundation of effective RevOps. • You’re comfortable getting deep into systems and technical details while keeping the broader business objective in mind. • You take ownership and don’t need a playbook to get started. • You are curious about new technology, including AI and automation, and think critically about where it can create meaningful business value. • You’re an effective cross-functional partner who understands that successful RevOps solutions start with understanding the people and processes they support. • You are comfortable operating in a PLG and/or PLS environment and understand how operational processes and systems need to support both self-serve and sales-assisted customer journeys. Bonus: • HubSpot certifications, including HubSpot Certified Administrator, HubSpot Marketing Software, or HubSpot Sales Software. • Experience integrating GTM technologies directly as well as using Zapier or similar integration and automation platforms. • Experience working in an organization supporting both PLG/self-serve conversion and PLS/sales-assisted conversion models. • Demonstrated proficiency with tools such as Aircall, Sakari, Gong, Zendesk, Stripe, Hippovideo, Guru, and Asana. • Experience with AI-enabled Revenue Operations tools and automation. • Experience working with SaaS metrics such as pipeline conversion, velocity, retention, customer health, and productivity. Compensation Band: $90k-105k 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: 🏝️ 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 in the U.S. and 100% employer-paid premiums for Extended Healthcare and Dental in Canada • RRSP/401k match • Generous Parental Leave policy 🤝 Perks: • 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! 🤖 AI Notice At Roofr, we’re big fans of AI.