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$176k – $204k per year
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Hybrid (Toronto, Canada)
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First seen by Alion on Nov 11, 2026. TEKsystems scores A on the Alion truth index.

Overview
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Profile match
TEKsystems is a US technology services and IT staffing company headquartered in Hanover, Maryland, and a subsidiary of Allegis Group. It places IT professionals with client companies on contract and permanent assignments and also delivers managed services and projects in cloud, data and analytics, cybersecurity, digital experience and enterprise applications. Its job board lists client roles such as field service and data center technicians, full stack developers, data analysts, product owners and UX researchers in the United States and Canada.
Job Description:

The Senior Microsoft Upgrade Specialist will provide hands-on technical leadership and overall delivery oversight for the Clinic Information Management System (CIMS) upgrade. The role will lead and validate the on-premises modernization of Microsoft Dynamics CRM and SharePoint, including related SQL Server, SSRS, Windows Server, authentication, infrastructure, integration, environment, migration, and cutover dependencies.

The specialist will work across technical and project delivery streams to establish the upgrade approach, coordinate multidisciplinary teams, create the required project and technical artifacts, validate vendor recommendations, resolve technical gaps, and ensure the target solution is supportable and implementation-ready.

Reporting to: Director, Digital Solutions Delivery, or designate.

Must Haves:

Experience five years or more:

  • Experience with leading IT projects (new implementation, upgrades) from technical and overall delivery perspective.
  • Experience with creating project artifacts (project plan, schedule, etc.).
  • Experience with leading technical teams (development, infrastructure, etc.).
  • Experience with creating technical project artifacts (approach, environment strategy, RICE, etc.).
  • Experience with MS CRM (implementation, development, administration, upgrade).

Direct Experience with Complex Solutions that include Dynamics/SharePoint Integrations including:

  • Direct experience leading Dynamics CRM 2016 (8.x) to Dynamics 365 Customer Engagement 9.x On-Premises upgrades.
  • Direct experience leading SharePoint 2013 to SharePoint Subscription Edition upgrades through supported intermediate stages.
  • Customization and Integration(s) between Dynamics /SharePoint:
  • Experience modernizing SQL Server, SSRS, Windows Server, and Dynamics-SharePoint integrations supporting complex enterprise applications.

Key Accountabilities

·        Lead the CIMS CRM and SharePoint upgrade from a technical architecture perspective, including collaboration with the Project Delivery Lead and project team for planning, execution, readiness, and implementation activities.

·        Validate the upgrade paths for Dynamics CRM 2016 to Dynamics 365 Customer Engagement 9.1 On-Premises and SharePoint 2013 to SharePoint Subscription Edition.

·        Create and maintain technical project artifacts, including the upgrade approach, environment strategy, architecture documentation, RICE inventory and assessment, migration sequencing, deployment plan, cutover plan, rollback plan, and technical readiness checklist.

·        Work with Project delivery lead to coordinate cross-functional technical teams, including application development, infrastructure, database, security, testing, operations, and third-party vendor resources.

·        Provide hands-on Microsoft Dynamics CRM leadership across implementation, development, administration, configuration, troubleshooting, and upgrade activities.

·        Provide technical leadership for SharePoint On-Premises farm architecture, upgrade planning, database migration, patching, integration, and operational readiness.

·        Assess infrastructure, database, security, identity, authentication, certificates, service accounts, network, integration, and application dependencies.

·        Confirm Microsoft supportability requirements, supported platform versions, prerequisite software, required patch levels, licensing considerations, and target-state configuration decisions.

·        Validate the transition from the current Dynamics and SharePoint client-to-server integration to the required server-to-server integration model.

·        Document and validate migration sequencing, outage planning, staffing coordination, test cycles, production cutover, rollback, and post-implementation stabilization planning.

·        Identify technical risks, unsupported configurations, architecture gaps, delivery constraints, and remediation recommendations, and escalate decisions requiring leadership direction.

·        Provide clear technical briefings, status updates, recommendations, and decision materials to project sponsors, IT leadership, governance bodies, and stakeholders.

·        Challenge assumptions and vendor recommendations where required and provide independent technical assurance throughout the upgrade.

Required Skills & Experience

·        Demonstrated experience leading complex IT projects, including new implementations, upgrades, migrations, and modernization initiatives, from both technical and overall delivery perspectives.

·        Proven experience creating and managing project artifacts such as project plans, schedules, work breakdown structures, dependency maps, risk and issue logs, decision logs, and implementation plans.

·        Proven experience leading multidisciplinary technical teams across development, infrastructure, database, security, testing, operations, and vendor workstreams.

·        Proven experience creating technical project artifacts, including upgrade approaches, environment strategies, architecture designs, RICE inventories, migration plans, release plans, cutover plans, rollback plans, and readiness assessments.

·        Deep hands-on experience with Microsoft Dynamics CRM, including implementation, development, customization, administration, configuration, troubleshooting, integration, and upgrades.

·        Direct experience with Dynamics CRM 2016 and Dynamics 365 Customer Engagement 9.x On-Premises.

·        Deep hands-on experience with SharePoint On-Premises, including SharePoint 2013, SharePoint 2016, and SharePoint Subscription Edition.

·        Experience delivering on-premises to on-premises Microsoft platform upgrades without relying on a cloud migration as the target solution.

·        Strong technical knowledge of SQL Server, SSRS, Windows Server, Active Directory, IIS, certificates, service accounts, authentication, networking, backup, recovery, and high availability.

·        Experience with Dynamics CRM and SharePoint integration, including server-to-server authentication and the modernization of legacy integration models.

·        Experience planning and leading environment builds, data and database migrations, system testing, performance validation, production cutovers, rollback, and stabilization.

·        Strong leadership, facilitation, problem-solving, risk management, documentation, and executive communication skills.

Key Deliverables

·        Validated technical upgrade strategy and implementation roadmap.

·        Integrated project plan and schedule with milestones, dependencies, resource needs, and decision points.

·        Current-state and target-state architecture documentation and supportability matrix.

·        Upgrade approach, environment strategy, and RICE inventory and assessment.

·        Dynamics CRM and SharePoint integration migration design.

·        Technical risk register, decision log, readiness assessment, and remediation plan.

·        Detailed migration, testing, cutover, outage, rollback, and stabilization plans.

·        Recommendations, and architecture review materials.

Preferred Experience

·        Direct experience leading Dynamics CRM 2016 (8.x) to Dynamics 365 Customer Engagement 9.x On-Premises upgrades.

·        Direct experience leading SharePoint 2013 to SharePoint Subscription Edition upgrades through supported intermediate stages.

·        Experience modernizing SQL Server, SSRS, Windows Server, and Dynamics-SharePoint integrations supporting complex enterprise applications.

·        Experience working in public-sector, justice, healthcare, or other highly regulated environments.

·        Relevant Microsoft certifications in Dynamics, SharePoint, infrastructure, security, or solution architecture.

Education

University degree in Information Technology, Computer Science, Engineering, or a related discipline, or an equivalent combination of education and directly relevant experience.

Success Measures

·        The on-premises target architecture, versions, prerequisites, patch levels, integrations, and licensing considerations are validated and documented.

·        Technical and delivery plans are complete, sequenced, risk-informed, and ready for execution.

·        Cross-functional teams and vendors have clear responsibilities, dependencies, milestones, and decision points.

·        Cutover, outage, staffing, rollback, and stabilization requirements are confirmed before production implementation.

·        LAO receives independent technical assurance that the proposed CIMS upgrade is supportable, achievable, and operationally ready.

Job Type & Location

This is a Contract position based out of Toronto, ON.

Pay and Benefits

The pay range for this position is $125.00 - $145.00/hr.

Individual compensation offered for this position within this range will depend on many factors, including qualifications, skills, relevant experience, job knowledge, geographic location, internal equity, and other pertinent job-related factors.

Job Type & Location

This is a Contract position based out of Toronto, ON.

Workplace Type

This is a hybrid position in Toronto,ON.

À propos de TEKsystems et TEKsystems Global Services

Nous sommes un fournisseur de services aux entreprises et de technologies. Nous accélérons la transformation de nos clients. Notre compétence en stratégie, conception, exécution et opérations libère la valeur de lentreprise par un éventail de solutions. Nous sommes une équipe de 80 000 personnes qui collaborent avec plus de 60 000 clients, notamment 80 % du Fortune 500 en Amérique du Nord, Europe et Asie, qui collaborent avec nous dans le cadre de nos capacités full-stack et notre rythme. Nous sommes des penseurs stratégiques, des collaborateurs pratiques qui aident les clients à exploiter le changement et maîtriser le dynamisme de la technologie. Nous bâtissons le futur en livrant les résultats et en créant un impact positif dans nos communautés mondiales. TEKsystems et TEKsystems Global Services sont des entreprises dAllegis Group. Découvrez dautres informations à TEKsystems.com.

Ordonnance sur légalité des chances de San Francisco: Conformément à lOrdonnance sur légalité des chances de San Francisco, pour tous les postes situés dans la ville et le comté de San Francisco, nous examinerons les candidatures des personnes qualifiées ayant un casier judiciaire ou des antécédents criminels.

Utilisation de lintelligence artificielle (IA): Nous pouvons utiliser lintelligence artificielle (IA) pour soutenir certaines étapes de notre processus dembauche, notamment la recherche, la présélection et lévaluation des candidatures. LIA aide à analyser les candidatures et les qualifications, mais les décisions finales sont prises par notre équipe de recrutement. En soumettant votre candidature, vous reconnaissez et acceptez que celle-ci puisse être examinée à laide doutils dIA.

About TEKsystems and TEKsystems Global Services

Were a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. Were a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. Were strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. Were building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

San Francisco Fair Chance Ordinance: Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.

Use of Artificial Intelligence (AI): We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.econnaissez et acceptez que celle-ci puisse être examinée à laide doutils dIA.

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