PolicyMe

• Design customer journeys across the full lifecycle, from acquisition and onboarding through retention and re-engagement. • Continuously test, measure, and optimize campaigns through A/B testing and performance analysis. • Design email and lifecycle assets using AI (Claude), then build them as modules and templates in HubSpot. • Build and maintain the workflows that power our customer journeys — enrolment logic, triggers, branching, segmentation to deliver highly personalized customer experience. • Partner with Product, Growth, Design, and Data teams to launch campaigns supporting new products, features, and business initiatives. • Monitor lifecycle performance metrics and identify opportunities to improve customer engagement, conversion, retention, and lifetime value. • Help grow lifecycle marketing into a scalable function as PolicyMe expands.

• Develop the go-to-market strategy for our newest opportunities – new customer segments, newly launched product lines, and future partner launches. • Build deep customer and market understanding through primary research: customer conversations, advisor call reviews, funnel data, and competitive pricing analysis. • Own the go-to-market strategy for new and existing customer segments, determining who we target, how we win, and what drives profitable growth, while partnering with cross-functional teams to bring that strategy to market. • Define which customer segments we can win profitably, and prioritize where we invest. • Design and run go-to-market experiments with a dedicated test budget: validate segments, messages, and channels at small scale before we invest at volume. • Make clear calls on what to scale, iterate, or kill – backed by data. • Build playbooks from what works so the broader team can run them, then move to the next opportunity. • Strengthen the positioning and point of view across our highest-performing product line, working closely with our content and paid teams. • Bring the voice of the customer into how we market – grounded in research, not assumptions. • Coordinate launch readiness with Product, Sales, and Operations so new products ship with go-to-market behind them. • Over time, build context on our B2B2C partner programs to support future partner launches.

• Lead and manage a team of fullstack/AI engineers, provide mentorship, performance feedback and enable career growth for the team • Oversee technical design, development and deployment of fullstack web applications backed by AI technology • Collaborate with product, design, and QA teams to ensure seamless execution and delivery of cross-functional projects. • Drive architecture decisions for scalable, reliable, secure cloud-based AI platforms that align with business objectives • Foster an innovative environment for exploring state-of-the-art AI techniques • Lead technical decision-making ensuring alignment with product/company objectives • Promote continuous learning and uplift team's expertise in emerging AI technologies

• Define & Own the Product Vision - Evolve our product strategy to improve customer delight, retention, referral growth, operational efficiency, and cross-product adoption. - Develop a compelling long-term vision for how to make insurance simple for Canadians, from how customers discover new products of ours to how they manage it post-sale. - Build and champion a roadmap that balances innovation, operational excellence, and long-term scalability. - Develop a deep understanding of customer and operational pain points, using those insights to shape strategy and prioritization. - Establish clear OKRs and success metrics that align teams around measurable business and customer outcomes. • Solve Ambiguous Problems - Take open-ended, unstructured problems and break them down into clear opportunities, strategic priorities, and executable plans. - Bring creative, first-principles thinking to solve complex challenges that have not been solved before in the Canadian insurance market. - Balance customer needs, technical constraints, operational realities, and business priorities when making product decisions. - Lead through ambiguity and create clarity for teams and stakeholders across the organization. • Drive End-to-end Execution and Delivery - Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration. - While you’ll shape the strategic direction, you’re also highly execution-oriented and willing to dive into the details when needed. - Ensure we build the right things, the right way, at the right time by balancing short-term wins with long-term platform investments. - Collaborate closely with Product Design and Engineering to build best-in-class customer and internal product experiences. - Write clear, actionable product specifications that connect business goals, customer needs, operational requirements, and technical constraints. - Coordinate closely with Growth, Customer Success, Operations, and other stakeholders to ensure launches are operationally ready and well-supported. - Drive alignment across teams and act as the connective tissue between stakeholders with competing priorities. • Measurement, Experimentation and Iteration - Define success metrics and measurement frameworks for all major initiatives, including customer engagement, funnel conversion, retention, operational efficiency, and long-term customer value. - Design and run experiments to validate hypotheses, de-risk larger investments, and accelerate learning. - Partner closely with Data to build dashboards, analyze product performance, and translate insights into actionable next steps - including when to pivot, double down, or sunset initiatives. - Use data, customer insights, and business context to continuously refine strategy and prioritization.

• Design and develop full stack features for our AI-powered web application using Python, React, Redux, PostgreSQL, and AWS • Integrate AI models and APIs for tasks like document processing, data extraction, recommendation engines etc. • Work closely with Sr. Engineers experienced in AI to seamlessly integrate models into production • Research and prototype new AI applications to continuously enhance our product capabilities • Construct scalable, secure, and observable cloud architectures for our core AI services • Implement robust data pipelines to fuel AI model training and inference • Craft seamless user experiences that surface AI-powered functionality • Participate in architecture planning, code reviews, and ideation sessions • Take ownership of feature development end-to-end (once ramped up), coordinating with QA and other teams • Engage in cross-team communication to help unblock dependencies and improve release flow • Share ideas during quarterly planning to help shape what we build next • Participate in company-wide initiatives such as hackathons, engineering guilds, and AI tooling experiments

• Develop full stack features for our AI-powered web application using Python, React, Redux, PostgreSQL and AWS • Integrate AI models and APIs for tasks like document processing, data extraction, recommendation engines etc. • Work closely with Sr. Engineers experienced in AI to seamlessly integrate models into production • Stay current on emerging AI technologies/frameworks and explore new applications • Build scalable, reliable backend services to fuel our AI workflows • Create intuitive user experiences that surface AI-powered capabilities • Participate in architecture planning, code reviews, and ideation sessions • Take ownership of feature development end-to-end (once ramped up), coordinating with QA and other teams • Engage in cross-team communication to help unblock dependencies and improve release flow • Share ideas during quarterly planning to help shape what we build next • Participate in company-wide initiatives such as hackathons, engineering guilds, and AI tooling experiments

• Own and lead the Talent Acquisition function at PolicyMe, helping shape how we hire and scale the company, while also owning key roles yourself across technical and business functions, with a strong focus on Product and Engineering hiring. • Partner closely with hiring managers to define hiring needs, align on candidate profiles, and move searches forward effectively. • Lead sourcing efforts across outbound channels, referrals, networking, pipeline-building initiatives, and early talent hiring programs to attract high-quality talent. • Support scalable, high-quality hiring across the company by identifying bottlenecks, improving recruiting workflows, and strengthening interview processes and manager calibration practices. • Use recruiting data, market insights, and funnel trends to help inform hiring decisions and improve overall recruiting performance. • Own recruiting reporting and dashboards, using hiring metrics, funnel data, and market insights to help improve recruiting performance and support hiring decisions. • Work closely with leadership and the broader People team through a highly collaborative, fast-moving environment that requires constant communication and quick alignment.

• Leading the design and development of full stack features for our AI-powered web application using Python, React, Redux, PostgreSQL, and AWS • Defining the technical vision and architectural principles for AI/ML systems • Driving innovation by researching and prototyping cutting-edge AI technologies • Ensuring security, scalability, and observability best practices across cloud architecture • Work within a cross-functional environment partnering closely with product, design, and business teams to communicate technical designs/strategies • Serve as a role model for engineering standards and bring consistency across systems and processes while mentoring junior and intermediate engineers • Help drive sound technical decision-making across ambiguous, system-spanning problems

• We’re on a mission to modernize insurance – making it simpler, more accessible, and customer-first. • This product leadership role will have end-to-end ownership over the product vision, the strategy, and the execution of our Life and Critical Illness product roadmap. • Evolve our product strategy to meet ambitious growth, retention, and customer impact goals that you will own. • Set a compelling long-term product vision for our Life and Critical Illness vertical, aligned with business priorities and grounded in customer insights. • Ensure we build the right things, the right way, at the right time – balancing short-term wins with long-term platform evolution. • Collaborate closely with Product Design to build best-in-class customer experiences. • Write clear, actionable product specs that connect business goals, customer needs, and technical constraints. • Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration.

• Participate in daily QA standups and the standups of your dedicated engineering team, staying close to requirements, specs, and release plans. • Assist in building comprehensive testing plans with the QA team and design clear test cases for assessing each feature's readiness for deployment. • Manage all aspects of the test plan to enable an on-time launch, including independently executing test cases, documenting progress for traceability purposes, and communicating testing statuses to key stakeholders (engineering, product, customer success etc.). • Perform thorough manual testing across environments, devices, and browsers, including regression and exploratory testing around frequent releases. • Log, track, and retest bugs in Jira and Zephyr, working with developers to prioritize and resolve issues effectively. • Work with QA, product and engineering teams to identify possible new tools or internal features that can improve QA testing quality and speed. • Contribute to our AI-supported QA automation project (e.g. TestSigma), helping identify scenarios for automation and supporting the creation and maintenance of automated tests. • Support developers to improve automated testing, ensuring new features are added to our automated regression testing suite where appropriate. • Work with product managers to identify which bugs must be resolved before deployment and which are not critical path. • Help develop and execute a structured process for triaging bugs identified across the organization. • Detail out bugs to support resolution with the engineering team, including bug replication and root cause analysis.