Since 2012, Rightsline has been making work easier for rights and royalties professionals with our innovative rights and royalties management software, allowing our customers to maximize their portfolios without having to max out their daily to-do-lists.

Our fully integrated and configurable platform provides customers with comprehensive access to all their rights and royalties, across all markets and platforms, instantly. Departments can communicate, collaborate, and cohesively take action without worrying about mistakes; and in-app reports and timely alerts ensure our customers never miss an chance to do more.

The Position Reporting to the VP of Strategy, the Corporate Strategy Lead serves as a right hand on Rightsline’s highest-priority company initiatives. You will help drive annual and quarterly planning, maintain a sharp view of the market and competitive landscape, take on high-stakes strategic analysis, and produce the materials leadership and the board rely on, partnering closely with Product, Engineering, Go-to-Market, Finance, and Operations. You will also help steer a focused set of cross-functional programs, including Rightsline’s AI initiatives, from business case through measurable results. This role is based in Canada, with a preference for candidates in the Greater Toronto Area (GTA).

Mission & Impact You will be one of a small number of people with full visibility across the company. This role turns leadership’s direction into committed priorities, clear plans, and measurable goals, and makes sure the work that matters most actually lands. Success will be measured by the quality and adoption of the strategic plan, the influence of your analysis on key decisions, the on-time delivery of the cross-functional initiatives you own,



and the clarity of the executive and board materials you produce.

What You Will OwnStrategic Planning & Performance

Help lead annual and quarterly strategic planning: shape the framework, drive the analysis, and turn diverse input into a set of committed priorities and measurable goals.

Establish and maintain the cadence for tracking progress against company priorities and OKRs, flagging risks early and recommending course corrections.

Partner with Finance to connect strategic priorities to budgets, resourcing, and financial targets.

Market Intelligence & Strategic Analysis

Maintain a sharp, current view of the rights, licensing, and royalties landscape, including competitors, adjacent entrants, buyer behavior, and market trends.

Take on the strategic questions that do not have a natural owner: pricing and packaging, segment prioritization, build-versus-buy-versus-partner decisions, and M&A; evaluation.

Build business cases and financial models from ambiguous inputs, stress-test assumptions, and deliver a clear recommendation.

Executive & Board Communication

Produce the crisp, well-reasoned materials that leadership and the board rely on, with a explicit point of view rather than a data dump.

Prepare the VP of Strategy and executive team for board meetings, leadership offsites, and investor discussions.





Translate complex analysis into concise one-page summaries and slides that drive decisions.

Cross-Functional Initiatives, Including AI

Lead high-priority initiatives that span functions and have no natural home, building alignment through clarity and credibility rather than authority.

Support the prioritization and business cases for Rightsline’s AI initiatives, partnering with the Product and Engineering leaders who own delivery.

Define baselines and success metrics for strategic initiatives, measure results honestly, and recommend when to scale, adjust, or retire an effort.

What You Will Bring

4–5 years of experience spanning management consulting (or a comparable strategy environment) and an in-house strategy, BizOps, corporate development, or program leadership role. The consulting-plus-operating combination matters: we want the analytical discipline and the experience of having actually shipped something.

Strong analytical and financial modeling skills. You are comfortable building a business case from ambiguous inputs, stress-testing your own assumptions, and defending the answer.

A track record of owning complex, cross-functional initiatives end to end, not just planning them. You can point to outcomes you were accountable for.

Exceptional written and verbal communication. You can compress a messy problem into one page or one slide and make a recommendation you are willing to be judged on.

The ability to lead through influence in a fast-moving, resource-constrained environment where priorities shift and the answer is rarely handed to you.

A working understanding of AI and how it is changing software businesses, enough to evaluate

📌 Corporate Strategy Manager (Winnipeg)
🏢 Rightsline
📍 Winnipeg