Digital Collaboration Services Consultant

CNA Insurance • Chicago, IL

1d • $72,000 - $141,000 • Hybrid

About The Position

You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential. We are seeking an individual contributor who will own and evolve our Digital Collaboration Services as a visionary Service Owner with a Product Owner mindset. In partnership with Architecture and Digital Workplace Enablement team, you will define the roadmap, guide engineering priorities, and drive adoption of modern collaboration and AI capabilities, while operational execution is primarily delivered through a Managed Service Provider (MSP). Your scope spans both modern Microsoft platforms - Microsoft 365 (Teams, SharePoint Online, OneDrive), Power Platform, Power BI, Microsoft Copilot and legacy collaboration technologies such as Lotus Notes and ShareFile, ensuring a stable user experience while enabling modernization and migration strategies. JOB DESCRIPTION: What You'll Do:

Requirements

• Solid knowledge of and experience with various technologies relevant to Workplace services including experience in Windows 11, Office 365, Teams, Exchange, SharePoint, OneDrive and ideally Microsoft’s Enterprise Mobility + Security (EM+S) suites as well as knowledge of other Technology service areas to ensure Technology alignment.
• Azure AD and PowerShell should be a hands-on skill or at a level capable of directing others.
• Deep expertise in Microsoft 365 collaboration (Teams, SharePoint Online, OneDrive) and strong working knowledge of Power Platform, Power BI, and Microsoft Copilot (or demonstrated ability to ramp quickly).
• Experience owning services/products in an enterprise setting: roadmap planning, backlog prioritization, iterative delivery, and value-based decision-making.
• Strong financial acumen with proven track record of developing and managing to a service/product budget while executing cost savings initiatives.
• Proven ability to influence engineering outcomes in a vendor/MSP model—setting direction, reviewing designs, and ensuring delivery quality and operational readiness.
• Experience supporting or transitioning legacy collaboration platforms such as Lotus Notes and/or ShareFile, including lifecycle management and modernization planning.
• Strong stakeholder leadership and communication skills—able to translate technical capabilities into business outcomes and adoption plans.
• High learning agility and curiosity for emerging Microsoft capabilities, with a pragmatic approach to governance, risk, and security.
• Bachelor’s degree in Computer Science / IT (or equivalent experience).
• 7+ years in enterprise collaboration/digital workplace platforms, including vendor/MSP ecosystems and modernization initiatives.
• Experience in a business-facing IT role or similar experience providing customer service for an IT service.
• Experience with agile delivery (refinement, planning, reviews) and outcome measurement (KPIs/OKRs, adoption analytics).
• Strong vendor management experience, including SLA/OLA performance management and continuous service improvement.
• Willingness and ability to lead and provide mentorship to other Infrastructure vendor managers.
• Microsoft certifications (M365, Azure, Power Platform) and experience with enterprise governance/security patterns

Responsibilities

• In collaboration with Architecture and the Digital Workplace Enablement team, own the product vision and roadmap for digital collaboration services, balancing modernization with stability across Microsoft 365 and legacy platforms (Lotus Notes, ShareFile).
• Guide engineering direction (MSP-led execution) across Teams, SharePoint Online, OneDrive, Power Platform, Power BI, and Copilot—ensuring solutions are secure, scalable, and operationally ready.
• Provide platform leadership for legacy services (e.g., Lotus Notes, ShareFile): oversee lifecycle management, risk reduction, and roadmap planning for rationalization/migration where appropriate.
• Drive AI enablement and Microsoft Copilot adoption, partnering with AI & Digital Enablement, Architecture, and Information Security to prioritize use cases, readiness, governance, and measurement.
• Advise business and technology leaders on upcoming Microsoft capabilities, roadmap changes, and adoption opportunities; proactively plan for platform changes and deprecations.
• Ensure reliability and user experience by overseeing MSP delivery against SLAs and leading continuous improvement (automation, self-service, knowledge management).
• Lead technical escalations: guide troubleshooting, root-cause analysis, and prevention of recurring incidents across both modern and legacy platforms.
• Partner cross-functionally with Security, Legal/eDiscovery, HR, and business stakeholders to ensure governance, compliance, and secure collaboration practices.
• Drive change enablement through communication plans, training and adoption programs, and stakeholder engagement aligned to business outcomes.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level