Role overview

The Position

This role reports to the VP of Strategy and serves as their right hand on Rightsline’s highest-priority initiatives. You will own the company’s portfolio of AI programs end to end — from identifying where AI creates durable advantage, to building the business case, to driving delivery across product, engineering, go-to-market, and operations, to proving the impact landed. Roughly 60–70% of your time will be spent on AI initiatives, with the remainder on core strategy work including annual and quarterly planning, market and competitive analysis, and board-level materials. You will be one of a small number of people with full visibility across the company.

We are looking to fill this role in Canada, with a preference for candidates based in the Greater Toronto Area (GTA).

What you will do:

Build the AI opportunity map.Work across product, engineering, go-to-market, and finance to identify where AI meaningfully changes our workflows, or our own cost to serve — then rank ruthlessly by value, feasibility, and time to proof.
Drive delivery.Run the AI portfolio day to day: stand up pilots, unblock teams, chase dependencies, and hold a high bar on pace. You will be closer to the work than a traditional PMO lead.
Prove the value.Instrument every initiative. Help define the baseline before launch, measure honestly after, and report both the wins and the misses. Retire what is not working and say so early.
Build internal AI fluency.Establish the lightweight standards, enablement, and internal adoption practices that make AI a default tool for how Rightsline works, not a special project.
Planning.Help run annual and quarterly strategic planning: shape the frame, drive the analysis, and turn a room full of opinions into a set of committed priorities and measurable goals.
Market and competitive intelligence.Maintain a sharp, current view of the rights, licensing, and royalties landscape — competitors, adjacent entrants, buyer behavior, and more.
Strategic analysis on demand.Take on the questions that do not have an owner: pricing and packaging, segment prioritization, build-versus-buy-versus-partner, and M&A.
Executive and board communication.Produce the crisp, well-reasoned materials that leadership and the board rely on — with a clear point of view, not just a data dump.
Cross-functional execution.Lead initiatives that span functions and have no natural home, building alignment through clarity and credibility rather than authority.

What you will bring to the role

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 scar tissue of having actually shipped something.
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.
Genuine analytical and financial modeling strength. You are comfortable building a business case from ambiguous inputs, stress-testing your own assumptions, and defending the answer.
Practical, current fluency with AI and machine learning — what large language models do well, where they fail, what retrieval and evaluation actually involve, and how to tell a real use case from a demo. You do not need to write production code, but you do need to earn the respect of engineers.
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 bias toward action, comfort with ambiguity, and low ego about doing the unglamorous work that makes a program succeed.
Bachelor’s degree in business, economics, engineering, computer science, or a related field — or equivalent practical experience.
A Lifelong Learner. We’re growing fast, so to keep up with us you’ll need to be personally focused on training, self-improvement, and professional development
Collaborative and coachable mentality that prioritizes ‘we’
Desire to break the status quo and build something awesome.

Nice to have:

Experience in B2B SaaS, ideally enterprise software sold to media, entertainment, publishing, or music companies.
Domain exposure to rights, licensing, royalties, content distribution, or intellectual property — or the demonstrated ability to get deep in a complex domain quickly.
Hands-on experience taking an AI or ML capability from concept to production, including the messy parts: data readiness, evaluation, change management, and adoption.
MBA or another relevant advanced degree.
Experience supporting board or investor reporting, or working in a private-equity-backed or high-growth company.
Familiarity with modern planning and delivery practices — OKRs, portfolio prioritization, agile working models.