Job Description
Description
Location: Canada, Remote (Toronto preferred)
Duration: 6 months contract (with the possibility of extension)
We are seeking a senior-level strategy professional to join our client in a highly visible, front-end strategy role. This position focuses on defining and shaping technology operating models, executive planning cadence, and strategic priorities — with an emphasis on problem structuring, option development, and executive decision support rather than delivery execution.
You will work directly with senior technology and business leaders to frame ambiguous problems, develop strategic options, and produce executive-ready narratives that drive alignment and decisions across complex, cross-functional environments.
Key Responsibilities:
Strategy & Operating-Model Design
Lead hypothesis-driven problem definition for complex, ambiguous operating-model challenges (decision rights, governance, org design, ways of working, planning rhythms).
Design and evaluate strategic options, trade-offs, and target-state operating models, including phased roadmaps.
Support senior leaders in making high-impact decisions through structured analysis and clear recommendations.
Executive Planning & Alignment
Architect and run annual and quarterly planning processes for senior leadership groups.
Define planning cadence, decision gates, and artifacts that align cross-functional priorities and long-term objectives.
Facilitate executive working sessions, offsites, and QBRs to drive strategic alignment.
Executive Narratives & Communication
Develop concise, C-suite-ready narratives and presentation materials that influence resourcing, sequencing, and operating decisions.
Translate complex analyses into clear storylines focused on implications, choices, and outcomes.
Serve as a trusted thought partner to CIO-level and senior executive stakeholders.
Financial & Technology Context (Supporting)
Apply Technology Business Management (TBM) concepts to support strategic planning and financial narratives.
Partner with Finance and other stakeholders to align strategy with investment decisions.
Requirements
Must Have:
Strong background in strategy consulting or equivalent roles where front-end strategy and operating-model design were core.
Demonstrated experience leading operating-model redesigns, including decision-rights frameworks, governance models, and planning rhythms.
Deep expertise in hypothesis-led problem solving, structured analysis, and solution optioning.
Proven ability to design and run executive-level planning cadences (annual / quarterly).
Exceptional executive communication skills, with a track record of authoring C-suite narrative decks that drove decisions.
Nice-to-Have:
Working fluency with TBM concepts to support planning and financial storytelling.
Experience operating in large, complex enterprise technology environments.
Exposure to technology strategy, digital, or IT transformation contexts.
