Senior Operations Specialist (Remote)

At Roofr, we’re obsessed with our customers. 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. 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 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.
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.
Leverage connectors such as Fivetran, Zapier, or similar platforms to connect systems and improve data flow.
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.
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.
Work closely with leaders and ICs across Sales, Marketing, Customer Success, and Enablement to inform your roadmap and prioritize initiatives.
Partner with Enablement to support training and adoption of new tools and processes.
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.
• Excellent written and verbal communication skills, with the ability to translate technical concepts into clear, actionable recommendations.

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 are curious about new technology, including AI and automation, and think critically about where it can create meaningful business value.
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 working in an organization supporting both PLG/self-serve conversion and PLS/sales-assisted conversion models .
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. Vacation/Paid Time Off:

• Flexible time off
• 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
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.
But when it’s time to chat, we’d love to meet you, not your AI alter ego. 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. 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.