Director of Revenue Operations

Overview of the role:

Join us at PolicyMe! We're modernizing insurance, and we'd like your help. Insurance is a $1T industry that has remained largely unchanged for decades and we want to change that. We're a remote-first, Toronto-based startup with big ambitions.

As the Director of Revenue Operations, you will drive operational excellence across the revenue lifecycle, working closely with sales, marketing, customer success, and product teams. You’ll manage a small, high-performing team, and execute strategic initiatives to support growth. Beyond supporting our growth ambitions, a critical part of your role will include exploring and integrating AI tools to enhance our customer-facing teams and operations, as well as implementing privacy and security measures to safeguard our systems and ensure compliance.

Reports To: COO

• Revenue Operations Strategy: Develop and execute an operations strategy aligned with company objectives. This will involve collaborating with the product team to operationalize new insurance products and tenant launches. Additionally, a large part of our strategy next year involves identifying opportunities to integrate AI into customer-facing teams and processes to improve efficiency, personalization, and customer satisfaction. You would lead the evaluation, implementation, and training of AI-driven tools for use in sales, and support functions.
• Team Leadership and Collaboration: Effectively lead a small team (3-5 members), fostering high performance and growth. Work cross-functionally with sales, marketing, customer success, engineering, and product teams to align efforts and achieve revenue goals.
• Tool and Process Management: Oversee and optimize the use of tools such as HubSpot (CRM), Aircall, Front Inbox, etc. Own vendor relationships with major tooling vendors and stay apprised of product roadmaps, best practices, etc. Proactively identify and resolve bottlenecks in processes to improve efficiency, scalability and performance.
• Data Management and Insights: Ensure data integrity and consistency across systems. Build and maintain dashboards in Looker to track and analyze key revenue, performance and operational KPIs. Provide actionable insights to the Director of Sales and VP of Growth to support forecasting and strategic decision-making.
• Customer Communications: In our CRM, own email and SMS communication workflows for customer-facing messages. With marketing and product, support the execution of automation strategies to improve customer engagement and retention.
• Privacy, Security, and Permissioning: Establish and enforce privacy and security protocols for systems and tools, ensuring compliance with industry standards and regulations. Build and maintain permissioning frameworks to manage access for customer-facing employees and protect sensitive data. Work collaboratively with engineering, and compliance teams to stay ahead of privacy requirements and implement best practices.

• 7+ years of experience in revenue operations, sales operations, or a related role, preferably in B2C, B2B2C or Fintech.
• Proven experience managing small teams and driving cross-functional initiatives.
• Expertise with CRM is essential (we use Hubspot, but Salesforce is fine!)
• Familiarity with AI tools and their application in customer-facing operations is a plus.
• Knowledge of privacy and security standards and experience implementing compliance protocols.
• Analytical mindset with a proven ability to interpret data and deliver insights.
• Effective communicator, skilled at aligning diverse teams to achieve common goals.

• Generous PTO - 20 vacation days
• Access to stock options and a comprehensive benefits plan
• A remote-first team with company paid, in-person socials and the option to work from our Toronto-based office
• Resources to help your professional development, including an L&D budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential
• Work with an empathetic, high-performing team in a flexible, results-oriented environment

About PolicyMe:

PolicyMe is a Venture-Backed InsurTech startup on a mission to put families first, protecting them with the honest and uncomplicated life insurance they deserve. Through technology, PolicyMe is streamlining the traditional insurance process, removing barriers and inefficiencies to deliver a fully-underwritten life insurance policy that families deserve but with fewer steps and lower costs. PolicyMe makes it easy to get a quote and apply for term life insurance online in 20 minutes or less. Since our launch in 2018, we have grown exponentially, selling over $1 billion in life insurance coverage to Canadians.

PolicyMe was also most recently voted as one of Canada's 50 Most Impactful Companies of 2021, and has been mentioned in BetaKit, National Post, the Global & Mail, Global News and more. If you're interested in being considered for this opportunity, please submit a resume.

Commitment to Equal Opportunity:

PolicyMe is proud to be an equal opportunity employer. All applicants will be considered for employment without attention to race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability status. We thank all applicants for their interest, however, only those selected for an interview will be contacted.

Accessibility Statement:

PolicyMe is dedicated to ensuring an accessible experience for all candidates. If you require accommodations during the application process, please let us know in the "Additional Information" section of the job application. We are committed to working with you to provide support and make reasonable adjustments throughout the process.