Senior Associate, Planning and Insights

Accountabilities: Develop and deliver executive-ready reports and dashboards to track key performance indicators, SaaS metrics, objectives, and key results (OKRs). Analyze business performance across customer acquisition, upselling, cross-selling, and churn to identify growth opportunities and emerging risks. Lead regular operational and performance reviews with leadership, translating complex data into clear, concise, and actionable recommendations. Build compelling performance narratives in collaboration with business leaders to support strategic discussions and decision-making. Translate analytical findings into recommendations that inform budgeting, product roadmaps, resource allocation, and quarterly planning. Conduct cohort analysis and customer segmentation to uncover trends, improve performance, and identify opportunities for growth. Develop and maintain forecasting models in partnership with business leadership, Finance, and Data teams. Collaborate with Product and Go-to-Market teams to assess strategic initiatives, model potential outcomes, and support prioritization decisions. Prepare business cases, conduct strategic analyses, and deliver ad hoc modeling to address emerging business questions and support leadership decisions. Requirements At least 5 years of experience in business operations, finance, business strategy, consulting, or a similar role within a high-growth company or startup. Strong financial modeling expertise and a demonstrated ability to use analytical approaches to solve complex business problems. Solid understanding of SaaS business models, performance indicators, and key growth and retention metrics. Expertise in data visualization and business intelligence tools, with the ability to create clear, insightful dashboards and reports. Experience using SQL, Python, or R for data manipulation, analysis, and extracting meaningful business insights. A proven track record of influencing business performance and driving growth through data-informed decisions. Experience with product-led growth (PLG) business models is highly desirable. Strong strategic thinking and commercial awareness, with the ability to connect quantitative analysis to business outcomes. Excellent communication and data storytelling skills, including the ability to explain complex findings to technical and non-technical audiences. Strong stakeholder management and influencing skills, with the ability to build trusted relationships and drive decisions across teams. A proactive, curious, and detail-oriented approach, combining analytical rigor with practical business judgment. Ability to move comfortably between high-level strategic planning and hands-on analytical execution. Must be eligible to work in Canada without employer sponsorship. Candidates based in the Greater Toronto Area are preferred, although applicants anywhere in Canada may be considered. Willingness to travel occasionally to company offices in Canada, the United States, or other North American locations as required. Benefits Competitive salary: Target annual base compensation of CAD $130,000–$145,000, depending on location, experience, skills, and market conditions. Flexible work arrangements: Work remotely from anywhere in Canada, with the option to work from an office or adopt a hybrid arrangement where available. Wellness support: Access to wellness benefits and an annual wellness stipend. Paid time off: Three weeks of vacation to start, one paid volunteer day each year, and two floating holidays. Retirement savings: Registered Retirement Savings Plan (RRSP) with a 4% company match. Employee ownership opportunities: Access to an Employee Stock Purchase Program. Professional development: Ongoing investment in learning, skills development, and career growth. International collaboration: Work with distributed teams across multiple countries in a collaborative, remote-friendly environment. Occasional travel opportunities: Potential to connect with colleagues in Canadian and North American offices.