Chicago - Senior Collaboration Engineer

About us

At Winston Taylor, we set the standard, together.

Winston Taylor is a transatlantic law firm built for the businesses, people, and markets driving capital and innovation. Here, you're in the room. In the action. Sleeves rolled up.

You'll work with leading clients. Disruptors. Fast-growth companies. And help them to stay one step ahead of the moment and make critical decisions that shape their future. We're present in the U.S., U.K., Europe, Latin America, and the Middle East, combining the scale and speed that clients demand.

You'll be trusted with real responsibility from the outset and build experience through hands-on work. We take your progression personally. We provide the platform. You shape the work around your goals and aspirations.

Step into the moments that matter. Join Winston Taylor.

Position Summary

The Senior Collaboration Engineer owns the performance, reliability, and operational effectiveness of the Firm's Microsoft 365 collaboration services. This role leads service improvements, manages complex operational activities, and drives issue resolution to ensure a stable, secure, and high-performing collaboration platform. The position works closely with the Network Operations Center, Information Risk, and Identity teams to lead operational alignment and continuously improve service quality.

Position Responsibilities

• Own the health, performance, and reliability of Microsoft 365 collaboration services.

• Manage and improve mail flow security controls to ensure effective and stable operations.

• Lead root cause analysis and drive implementation of sustainable remediation solutions.

• Manage and drive Microsoft 365 service changes end-to-end, including planning, coordination, and execution.

• Lead collaboration with the Network Operations Center to reduce recurring issues and improve service quality.

• Partner with Information Risk, Identity, and Information Governance teams to ensure secure and compliant operations.

• Drive evaluation and controlled adoption of new features and capabilities in alignment with established standards.

• Serve as a senior escalation point for complex issues and lead resolution efforts.

• Improve documentation standards, operational processes, and service quality practices.

• Mentor team members and provide technical guidance across daily operations.

Experience, skills and qualifications

• Bachelor's degree in information technology, computer science, or a related field preferred, or equivalent professional experience demonstrating foundational technical expertise and the ability to deliver high-quality work product required.
• 7+ years of experience administering Microsoft 365 collaboration services, including Exchange Online, Teams, OneDrive, SharePoint, and related security and compliance capabilities, with demonstrated advanced functional expertise required.

  • Hands-on experience managing email flow security, including spam filtering, transport controls, and related mail hygiene practices, with strong attention to detail and commitment to accurate, high-quality results required.
  • Experience supporting Microsoft 365 service changes, resolving complex technical issues with sound judgment, and producing clear operational documentation and support procedures required.
  • Experience using common M365 automation solutions (PowerShell, Power Platform, Azure Automation) to improve the efficiency & consistency of administrative and operational tasks required.
  • Experience utilizing a data-driven approach and "shift-left" principles to optimize the M365 end-user experience and improve the efficiency & effectiveness of the technical support process preferred.
  • Experience designing & building Power BI dashboards, ETL pipelines, and data storage solutions in Azure and/or Microsoft Fabric preferred.
  • Demonstrated ability to manage responsibilities independently, adapt to changing priorities, and maintain accountability for timely and high-quality outcomes required.
  • Experience working with Information Risk, Identity, and Information Governance teams to support secure and effective Microsoft 365 operations through strong collaboration and shared problem solving desired.
  • Experience supporting data retention, compliance, or governance capabilities within Microsoft 365, including Purview, with awareness of operational risk and disciplined execution desired.
  • Experience supporting Microsoft Copilot implementation, adoption, or governance for business use cases, with openness to innovation and evolving technology trends desired.
  • Strong ability to communicate technical concepts clearly, adapt messaging to varied audiences, and work effectively with stakeholders across technical and business teams desired.
  • Demonstrated ability to manage multiple priorities, work independently, accept feedback, and contribute as a collaborative team member while maintaining accountability for results desired.
  • Functional Expertise - Demonstrates advanced subject matter expertise in Microsoft 365 collaboration services, including Teams, OneDrive, Exchange Online, and SharePoint Online, and applies that knowledge to deliver high-quality work product across complex operational scenarios. Embraces technology and innovation opportunities, stays current with platform capabilities and industry trends, and leverages a broad understanding of Information Technology environments, services, and operational dependencies to contribute meaningfully to projects and service improvements.
  • Operational Excellence - Optimizes processes, resources, and priorities to deliver accurate, timely, and high-quality results, often with limited supervision. Demonstrates disciplined execution, strong attention to detail, and a commitment to continuous improvement while managing multiple priorities efficiently, meeting deadlines, and maintaining a customer-focused mindset. Maintains flexibility in support of operational needs, including availability after hours as required.
  • Problem Solving & Judgment - Uses strong analytical, problem-solving, and decision-making skills to identify and resolve issues within area of expertise. Applies sound judgment to assess information, propose timely and actionable solutions, and implement sustainable improvements, at times with limited supervision based on complexity, while escalating as necessary to mitigate risk.
  • Communication & Collaboration - Communicates clearly and effectively both verbally and in writing, adapting messages for technical and non-technical audiences and presenting concepts in a way stakeholders at all levels can understand. Builds positive relationships, works effectively both independently and collaboratively, engages in active listening, considers diverse perspectives, and resolves conflicts constructively to support inclusive teamwork and team success.
  • Ownership & Accountability - Demonstrates ownership of responsibilities across the full job scope and is accountable for results. Independently manages workload, adapts to changing priorities, and maintains quality standards while remaining receptive to feedback and course-correcting when needed. Shows initiative to learn continuously, teach others, and mentor teammates and partners to strengthen overall team capability and effectiveness.

BENEFITS
Winston offers comprehensive benefits that provide a full spectrum of coverage and support for our full-time employees and their families. Additional information about benefits and rewards can be found here.

SALARY

Illinois applicants only: The target annual salary range for this role is currently $128,000-$167,000 based on a regular, full-time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.

We are an equal opportunity employer and welcome applicants from all backgrounds and experiences. #LI-DC2 #LI-HYBRID