The posting
Overview of the role:
We are launching a new Home & Auto insurance business unit, and you will build the revenue engine that supports it from the ground up. As Revenue Operations Manager, you will own the 0-to-1 design and implementation of the CRM, sales processes, reporting, and operating workflows that help this business acquire and serve customers at scale.
This is a hands-on builder role for someone who enjoys creating structure where little exists. You will shape how leads enter the funnel, how opportunities move through the sales process, how teams manage customer handoffs, and how leaders understand performance. You will administer and evolve HubSpot, connect it with the tools our teams rely on, and establish the data foundation for a new line of business.
You will work closely with Sales, Marketing, Customer Success, Finance, and Operations to translate an emerging business model into practical systems and repeatable processes. From defining the first pipeline stages and routing rules to launching dashboards and improving workflows, you will help create the operating backbone for Home & Auto while building scalable standards for the broader revenue organization.
You will be both a systems owner and a business partner: identifying what the business needs next, designing pragmatic solutions, and making sure each process is adopted, measured, and improved over time.
What you’ll do:
- Administer and continuously improve HubSpot, including objects, properties, pipelines, workflows, automation, permissions, validation, and reporting
- Maintain a scalable CRM architecture, including naming conventions, property design, object associations, required fields, lifecycle stages, and deduplication
- Manage user access, team permissions, provisioning, and system governance
- Monitor system health, investigate issues, and coordinate fixes with vendors and technical partners
- Design and optimize lead routing, pipeline stages, handoffs, lifecycle definitions, and data governance
- Build workflows and automations that reduce manual work, improve consistency, and help teams move faster
- Manage integrations and data flows between HubSpot, Five9, Front, and other business systems
- Identify friction across the customer journey and translate it into clear, scalable process improvements
- Build and maintain dashboards and reporting that provide visibility into pipeline, conversion, retention, productivity, and customer activity
- Support forecasting, planning, territory analysis, segmentation, capacity planning, and compensation analysis
- Partner with functional leaders to define metrics, establish reliable reporting, and improve confidence in the data
- Surface trends, risks, and opportunities—not just numbers—and help stakeholders act on them
- Gather requirements, evaluate options, and recommend solutions that balance business impact with operational effort
- Plan, test, document, and launch system changes with clear communication and change-management support
- Monitor results after launch and iterate based on user feedback, adoption, and business outcomes
- Create process documentation, system guides, and training materials that make the right way easy to follow
- Build trusted relationships across teams and deliver improvements with and through stakeholders
What we’re looking for:
- 5+ years of experience in revenue operations, CRM administration, business systems, sales operations, or a related field
- Strong, hands-on experience administering HubSpot CRM in a complex or growing organization
- Experience designing CRM workflows, automation, integrations, permissions, reporting, and data-governance practices
- Strong analytical and troubleshooting skills across systems, data, and business processes
- Experience gathering requirements, testing changes, managing releases, and documenting technical processes
- Strong spreadsheet and reporting skills, with the ability to turn messy data into clear insights
- A practical, solutions-oriented mindset and a bias toward action
- Clear written and verbal communication skills, including the ability to explain technical concepts to non-technical audiences
- A collaborative approach and the ability to influence across teams without relying on formal authority
- Exceptional attention to detail and a high bar for data quality
- Knowledge of, or experience working in, the insurance industry
- Experience supporting Five9, Front, Confluence, and Jira
- HubSpot Administrator certification or equivalent practical experience
- Familiarity with SQL, data modeling, APIs, webhooks, JSON, or workflow automation
- Experience with Looker, Tableau, Power BI, or a similar business-intelligence platform
- Experience with CRM release management, integration monitoring, or business-systems support
Why join us:
- Generous PTO - 20 vacation days
- A comprehensive benefits plan with premiums paid in full by PolicyMe
- Investment in your professional development, including an L&D budget, AI tooling budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential
- An extremely high performing, low-ego, remote-first team that is truly disrupting an old industry
- Option to work from home or our Toronto-based office (bonus: we cover the costs to bring all our employees in-person twice a year for experiential socials!)
- Access to stock options based on performance
- Compensation: The total target cash compensation for this role is $110,000 to $150,000 CAD, based on experience. We'll walk through the details together during the interview.
About PolicyMe:
At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast to coast. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to Canadians' evolving needs. We also offer B2B2C solutions, partnering with organizations to provide seamless digital insurance options. Founded by a team of insurance experts and technology entrepreneurs, PolicyMe is committed to making insurance simpler and more accessible. Since our launch in 2018, we have grown exponentially, selling over $10 billion in insurance coverage to Canadians.
We are proud of the team we’ve built and are excited for those that are yet to join us. We operate with a remote-first culture, attracting top talent from across Canada. If you’re looking for a fast-paced, collaborative environment, working alongside incredibly ambitious yet humble humans, we may be the right place for you! To learn more, visit www.policyme.com.
Additional Notes:
- Job Vacancy: This role reflects growth in our team and expanded operational scope. We’re hiring to support increasing demand and continue delivering an exceptional customer experience.
- Commitment to Equal Opportunity: PolicyMe is an equal opportunity employer. We welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.
- Accessibility Statement: We are committed to providing an accessible hiring experience. If you require accommodations during the application process, please indicate this in the “Additional Information” section of your application.
We thank all applicants for their interest, however, only those selected for an interview will be contacted.
