Customer Success Operations Specialist

Location: Toronto - West Mall - ON 17

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.

The CSOS plays a key role in team enablement and operational continuity, 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.

Key Areas of Responsibility

Program and Project Support

• 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 deadlines
• Understanding Microsoft programs, funded workshop engagements and co-sell motions.
• Maintain and improve the Program & Operations process guides and standard operating procedures in our knowledge base
• Supporting and educating the Microsoft practice where needed, while showcasing the end-to-end funding process.

Process Optimize, Governance and Compliance

• 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.

Partner Programs, Funding and Incentives

• Facilitating collaboration across CDW Delivery, Sales, Marketing, Operations, and Finance to ensure strategic alignment
• Supporting Microsoft Programs by driving alignment with CDW’s strategic goals and desired business outcomes
• Work 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.

Growth, Renewals and Enablement

• 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.

Minimum Qualifications

• 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.

Other Required Qualifications

• 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 skills
• Ability to leverage business acumen, political savvy, relevant experience, perseverance and communication skills to build credibility & influence.
• Strong organizational skills, attention to detail is vital, and the ability to multi-task, organize and prioritize.
• Ability and willingness to travel up to 50 percent, or as needed, to other CDW locations, meetings and client sites.

Preferred Qualifications

• Experience supporting Microsoft licensing, programs or operational processes
• Knowledge 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 and retain talent. As such, we are committed topaytransparencyand ensuring fair compensation for all our coworkers. Each of our roles is assigned asalaryrange that is informed by multiple sources of market data.We determineindividualpaywithin a given range based on a candidate's prior experience, knowledge, skills and abilities. This approach allows us to offer competitive and equitable salaries that reflect the value and responsibilities of each role at CDW. Salaries are based on a 40-hour workweek, and paid on a bi-weekly payroll schedule.

Pay range: $70,000- $ 96,400, depending on experience and skill set

CDW is committed to being an AI-fluent organization

We’re looking for people who bring curiosity, a learner’s mindset, and a willingness to engage with ever-evolving technology and tools. We value adopting AI as a partner, openness to experimentation, and a shared interest in learning together on AI. Our goal is to create a culture where AI enhances—not replaces—human creativity and decision-making. You don’t need to be an expert today; what matters is your readiness to explore, adapt, and grow with us as we integrate AI responsibly and effectively into our work.

Additionally, CDW is committed to fostering an equitable, transparent, and respectful hiring process for all applicants. During our application process, our goal is to understand your experience, strengths, skills, and qualifications. As an AI forward company, we see AI not just as a tool, but as a catalyst for new ways of thinking, creating, and communicating. We encourage candidates to embrace an AI mindset, one that’s curious, adaptive, and ready to explore what’s possible. We welcome thoughtful use of AI to expand your perspective and elevate how you share your story, while ensuring your application remains rooted in your own background, judgment, and voice.

About Us

CDW is a Fortune 500 technology solutions provider that helps businesses, government, education, and healthcare organizations achieve what’s possible through technology. What makes CDW different isn’t just what we do—it’s how we do it. 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. And we think forward—staying curious, moving fast, and continuously learning.

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 collaborative environment where your work matters, your growth is supported, and your contributions help shape what’s next.

Together, we deliver the full promise of what technology can do. Together, we Make Amazing Happen.

CDW is an equal opportunity employer. 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.