The Customer Success Operations Specialist (CSOS) enables the effectiveness, scalability, and operational excellence of Customer Success by translating strategic partnership priorities into consistent, scalable processes and day-to-day execution. The role works cross-functionally with CSMs, Sales, Licensing, Finance, Services, and Microsoft to ensure programs and offerings are effectively operationalized and delivered.The CSOS supports operations and program offerings end-to-end, from inception through implementation and ongoing execution. This includes agreement and licensing operations, program administration, reporting, platform enablement, process optimization, and the development of workflows, tools, training, and best practices that enable CSMs and supporting teams to achieve adoption, expansion, retention, profitability, and vendor program objectives.The role partners closely with Strategic Partnerships and Operations leads to optimize processes across the customer and sales lifecycle, maximize gross profit and Microsoft incentive opportunities at the customer level, and ensure accurate and timely execution through systems such as Salesforce and Gainsight.

The CSOS also supports the operationalization of emerging Microsoft requirements, programs, and services, ensuring they can be consistently adopted and scaled across CDW Canada.including new-hire onboarding, documentation and maintenance of Customer Success best practices, cross-training, reporting, and coordination of program communications. The role identifies opportunities to improve, automate, and standardize processes while ensuring the Customer Success organization has the systems, information, and operational support required to execute effectively.Support strategic Microsoft programs end to end, delivering KPIs and milestones on time, in scope and on budget, and prioritizing time against the opportunities with the strongest potential return.Be fiscally responsible for program results, and keep the project team accountable to deadlinesUnderstanding Microsoft programs, funded workshop engagements and co-sell motions.Maintain and improve the Program & Operations process guides and standard operating procedures in our knowledge baseSupporting and educating the Microsoft practice where needed, while showcasing the end-to-end funding process.Optimize, implement and manage scalable operational processes for CDW Customer Success.Continuously identify and investigate opportunities for process development and improvement, to ensure internal and external customer satisfaction and maximum efficiency.Lead our submission of the annual Partner compliance audit, act on the findings, identify and communicate audit results to mitigate operational risk.Update CDW/Microsoft SOP documentation to keep the Licensing Operations manual accurate, and work with CDW USA to leverage existing processes wherever the opportunity exists.Licensing and Software Operations Support Software Operations processes, including the Microsoft Enterprise Agreement T36 process, renewal management,



Software EDC maintenance, software contract management and vendor reporting tools, and assist with vendor performance tracking such as rebates and incentives.Support Contract Lifecycle Management, and process and invoice customer agreements across marketplaces, operationalizing the end-to-end journey accurately and on time.Enter all anniversary orders into our systems within Microsoft timelines, and complete annual Open Value, Select Plus, EES, MPSA and Indirect EA billings.Enter and manage CPOR claims and provide support on level 100 licensing inquiries.Work with internal teams and partners to keep quoting, ordering and deal registration running smoothly for Microsoft customers.Provide accurate and timely responses on operational processes to Software Product Managers, Licensing Specialists, Customer Success Managers and Sales.Facilitating collaboration across CDW Delivery, Sales, Marketing, Operations, and Finance to ensure strategic alignmentSupporting Microsoft Programs by driving alignment with CDW’s strategic goals and desired business outcomesWork directly with Microsoft to gather funding program updates to enable our workforce, covering ECIF, workshops, FastTrack, MDF, MCI Deployment programs and Adoption accelerators.Submit, track and claim Microsoft funding for all eligible programs, including workshop and funding claims.Support Microsoft funded programs to maximize return on investment.Collaborate with CDW’s Customer Success Microsoft practice leads and marketing to develop go-to-market strategies for promotional campaigns and customer-facing documentation.Support all CDW sellers with the tools, resources, and enablement needed to effectively lead Microsoft program discussions with customers.Support Licensing Specialists and Customer Success Managers (CSMs) in achieving on-time Microsoft renewals and true-ups by ensuring orders are processed by the deadline.Grow Services revenue by educating and promoting Microsoft Programs across the organization.Support virtual and in-person customer facing events that promote Microsoft and CDW services, and assist CDW sales and partner teams with field alignment and account mapping.Assist in developing and delivering Microsoft program training for CDW coworkers, and work with relevant departments to create and maintain collateral that promotes CDW Canada Solutions and Services capabilities.Tools, Reporting and Data Support tools and processes across customer management profile, reporting, and deal registration within all our toolsets.Track and report Microsoft weekly, monthly and annual performance, design reporting metrics with Operations,



and monitor campaign effectiveness to aid decision making and planning.Maintain pipeline opportunities with support from Customer Success Managers, Licensing Specialists and Sales.Take on other operational & support responsibilities as needed.Bachelor’s degree in business or a computer-related field, or equivalent experience.Three or more years of industry experience delivering quality technology solutions.Three or more years supporting technology projects across IaaS and cloud solution areas.One or more years in a Microsoft Licensing Operations role or equivalent experience.Experience supporting medium to enterprise customers and partners.Proven experience in project management and cross-departmental engagement, with demonstrated accountability for project results, fiscal responsibility, and the ability to lead teams to meet project deadlines.Knowledge of Microsoft Incentive programs.Proficiency with Microsoft Office applications, including CoPilot, Excel, Word, Outlook and PowerPoint.Excellent written, verbal and presentation skillsAbility to leverage business acumen, political savvy, relevant experience, perseverance and communication skills to build credibility & influence.Ability and willingness to travel up to 50 percent, or as needed, to other CDW locations, meetings and client sites.Experience supporting Microsoft licensing, programs or operational processesKnowledge of backbone departments, their responsibilities and their processes.Very strong business acumen & understanding of sales processes to support the growth of our business.At CDW, we strive to offer market-competitive total rewards packages to attract andretaintalent. Each of our roles isassignedasalaryrange that is informed by multiple sources of market data.Salaries are based on a 40-hourworkweek,andpaidon a bi-weekly payroll schedule.About UsCDW is a Fortune 500 technology solutions provider that helps businesses, government, education, and healthcare organizations achieve what’s possible through technology.

At CDW we act as one—building trust, speaking candidly, and working together to achieve more. We play to win—focusing on what matters most and delivering for our customers. We believe meaningful work happens when people feel supported, heard, and empowered to contribute.

That’s why we think of ourselves as coworkers, not just employees—working together to solve complex challenges and deliver real impact for our customers and communities.As a full‑stack, full‑lifecycle technology partner, CDW brings deep expertise, strong relationships, and broad industry knowledge to help turn ideas into outcomes. When you join CDW, you become part of a cooperative environment where your work matters, your growth is supported, and your contributions help shape what’s next.All qualified applicants will receive consideration for employment without regards to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status or any other basis prohibited by state and local law. #

📌 Customer Success Operations Specialist (Winnipeg)
🏢 CDW
📍 Winnipeg