Description

Deliverable: Support enterprise digital strategy, technology planning, and business case development for enterprise cloud and on-premises products and services.

Key deliverables include:

- Conduct current-state assessments of enterprise cloud and on-premises products and services, including technical, operational, financial, and capability analyses;
- Lead strategic options analyses, including stakeholder engagement, jurisdictional scans, and cost-benefit assessments;
- Support the development of enterprise digital strategies, technology roadmaps, implementation plans, and strategic recommendations;
- Lead the development of business cases, investment analyses, and executive decision-support materials;
- Facilitate workshops and collaborate with business, technical, and executive stakeholders to define strategic direction, business requirements, and success measures;
- Present strategic recommendations, business cases, and roadmaps to governance bodies and senior leadership;
- Develop reports, presentations, roadmaps, and other strategic planning artefacts to support enterprise technology planning and modernization initiatives.

Experience Requirements

Evaluation Breakdown

1. Enterprise Digital Strategy Experience 40%

Parameters:

Demonstrated experience developing enterprise digital strategies, technology roadmaps, business cases, and strategic recommendations for large, complex IT environments.



The proponents must demonstrate experience conducting current-state assessments, evaluating strategic options, and supporting executive decision-making.

2. Strategic Planning and Analysis – 20%

Parameters:

Demonstrated experience conducting strategic options analyses, including stakeholder engagement, jurisdictional scans, cost-benefit analyses, and investment assessments. The proponents must describe how recommendations, implementation roadmaps, and business cases were developed to support technology modernization initiatives.

3. Executive Communication and Stakeholder Engagement – 10%

Parameters:

Demonstrated ability to communicate complex strategic and technical concepts to executive audiences. The proponents must provide an example of preparing and presenting executive briefing materials, facilitating stakeholder workshops, and influencing strategic technology decisions.

Supplier Comments

Closing Date/Time: 2026-09-08, 12:00 p.m. EST.

Max submission: Two (2)

5 days onsite

Must Have:

- 5+ years’ experience as technical architect with expertise in enterprise strategy development.
- 5+ years of demonstrated experience conducting strategic options analyses, including stakeholder engagement, jurisdictional scans, cost-benefit analyses, and investment assessments.
- Experience developing strategy and architecture design for hybrid environments.

📌 Technology Architect (Toronto)
🏢 Softline Technology
📍 Toronto