Senior Technical CRM Architect

Flexstaf I.T. Inc.; Toronto; Hybrid; CAD 83,000 - 117,000; Full time

Job summary

Flexstaf I.T. Inc. in Toronto seeks a Senior Technical Architect / Upgrade Specialist to lead the CIMS upgrade project.

The role focuses on on-premises upgrades of Microsoft Dynamics CRM and SharePoint, overseeing SQL Server and SSRS migrations, authentication, and environment readiness, with a strong emphasis on technical leadership. You will coordinate multidisciplinary teams, validate upgrade paths, and create critical artifacts such as migration sequencing, deployment plans, and cutover

Qualifications

• 5+ years of experience leading complex IT projects, including upgrades and migrations.
• Proven ability to create and manage project artifacts (plans, schedules, risk logs).
• Experience leading multidisciplinary technical teams across development, infrastructure, database, security, testing, and operations.
• Experience creating upgrade approaches, environment strategies, and migration plans.
• Strong hands-on expertise with MS CRM, including upgrades and administration.
• Direct experience with Dynamics CRM 2016 to Dynamics 365 CE on-prem upgrades.
• Direct experience with SharePoint 2013 to SharePoint Subscription Edition upgrades.
• Experience integrating Dynamics CRM and SharePoint, including server-to-server authentication.
• Deep knowledge of SQL Server, SSRS, Windows Server, identity, networking, and security.

Responsibilities

• Lead the CIMS CRM and SharePoint upgrade from a technical architecture perspective, coordinating readiness and implementation activities.
• Validate upgrade paths for Dynamics CRM 2016 to Dynamics 365 CE and SharePoint 2013 to Subscription Edition.
• Create and maintain technical artifacts including environment strategy, migration plans, cutover, and readiness checklists.
• Coordinate cross-functional technical teams across development, infrastructure, security, testing, and operations.
• Provide hands-on leadership across implementation, development, administration, configuration, and upgrade tasks.
• Lead SharePoint On-Premises farm architecture, database migration, patching, integration, and operational readiness.
• Assess infrastructure, security, authentication, certificates, and networking dependencies.
• Document migration sequencing, outage planning, staffing, testing, and production cutover.

Skills

IT project leadership

Project artifacts

Leading technical teams

Technical artifacts

MS CRM

Dynamics CRM 2016

SharePoint upgrades

Dynamics-SharePoint integrations

SQL Server / SSRS

On-Premises upgrades

Education

University degree in IT/CS/Engineering

Tools

Dynamics CRM

SharePoint On-Premises

SQL Server

SSRS

Active Directory

IIS

Job description

Position: Senior Technical Architect /Senior - Upgrade Specialist and SharePoint Upgrade

Type: Contract

Duration: 3 – 6 months

Location: Toronto

Work Schedule: Hybrid

Work Model: 2 days onsite / 3 days remote

MANDATORY SKILLS

• 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.

ON-PREMISES FOCUS: This role supports an on-premises to on-premises upgrade. Migration to Microsoft cloud services is not in scope at this stage.

Primary Function

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.

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 escalation 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.
• 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.
• The organization receives independent technical assurance that the proposed CIMS upgrade is supportable, achievable, and operationally ready.

Required

• 5+ years of experience leading IT projects
• Experience with creating project artifacts
• Experience with leading technical teams
• Experience with creating technical project artifacts
• Experience with MS CRM
• Direct experience with Dynamics CRM 2016
• Direct experience with SharePoint 2013
• Experience with Dynamics-SharePoint integrations

Preferred

• Direct experience leading Dynamics CRM 2016 to Dynamics 365 Customer Engagement 9.x On‑Premises upgrades
• Direct experience leading SharePoint 2013 to SharePoint Subscription Edition upgrades