Description Deliverable: Supportenterprisedigitalstrategy,technologyplanning,andbusinesscasedevelopmentforenterprisecloudandon-premisesproductsandservices.
Keydeliverablesinclude:
Conductcurrent-stateassessmentsofenterprisecloudandon-premisesproductsandservices,includingtechnical,operational,financial,andcapabilityanalyses;
Leadstrategicoptionsanalyses,includingstakeholderengagement,jurisdictionalscans,andcost-benefitassessments;
Supportthedevelopmentofenterprisedigitalstrategies,technologyroadmaps,implementationplans,andstrategicrecommendations;
Leadthedevelopmentofbusinesscases,investmentanalyses,andexecutivedecision-supportmaterials;
Facilitateworkshopsandcollaboratewithbusiness,technical,andexecutivestakeholderstodefinestrategicdirection,businessrequirements,andsuccessmeasures;
Presentstrategicrecommendations,businesscases,androadmapstogovernancebodiesandseniorleadership;
Developreports,presentations,roadmaps,andotherstrategicplanningartefactstosupportenterprisetechnologyplanningandmodernizationinitiatives.
Experience Requirements EvaluationBreakdown 1.EnterpriseDigitalStrategyExperience40%
Parameters:




Demonstratedexperiencedevelopingenterprisedigitalstrategies,technologyroadmaps,businesscases,andstrategicrecommendationsforlarge,complexITenvironments.Theproponentsmustdemonstrateexperienceconductingcurrent-stateassessments,evaluatingstrategicoptions,andsupportingexecutivedecision-making.
2.StrategicPlanningandAnalysis–20% Parameters:
Demonstratedexperienceconductingstrategicoptionsanalyses,includingstakeholderengagement,jurisdictionalscans,cost-benefitanalyses,andinvestmentassessments.Theproponentsmustdescribehowrecommendations,implementationroadmaps,andbusinesscasesweredevelopedtosupporttechnologymodernizationinitiatives.
3.ExecutiveCommunicationandStakeholderEngagement–10% Parameters:
Demonstratedabilitytocommunicatecomplexstrategicandtechnicalconceptstoexecutiveaudiences.Theproponentsmustprovideanexampleofpreparingandpresentingexecutivebriefingmaterials,facilitatingstakeholderworkshops,andinfluencingstrategictechnologydecisions.
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 demonstratedexperienceconductingstrategicoptionsanalyses,includingstakeholderengagement,jurisdictionalscans,cost-benefitanalyses,andinvestmentassessments.
Experience developing strategy and architecture design for hybrid environments.

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📌 Technology ArchitectInfrastructure Technology Services (Ontario)
🏢 Softline™ Technology
📍 Ontario