CSS Technical Skilling Director

Main Location
Redmond, WA, United States
Open jobs

Are you passionate about building technical education that helps people advance their careers? Do you gain energy from leading teams through change and transformation? Would you jump at the opportunity to build and significantly expand a new team? The Technical Content Development team in Worldwide Learning is hiring for a newly formed leadership role, to lead a newly formed team focused on building a broad technical skilling curriculum for thousands of Microsoft support engineers. 


Microsoft Worldwide Learning’s mission is to build world class capability for customers, partners, employees and future generations, enabling them to develop, grow, and achieve success professionally. Within WWL, the Technical Content Development team’s mission is to help IT professionals, developers, and employees build their technical skills and advance their careersWe are a dynamic team of skilled and experienced content development, learning, and content portfolio management professionals, with a high-energy, diverse & inclusive, and iteration-driven culture, grounded in real customer and field needs. We build blended learning experiences that include Instructor Led Training (ILT), supported by interactive experiences and online training. We have tremendous opportunities not only to increase customer satisfaction, but also to innovate in the content we deliver.  


We are looking for a skilled and passionate leader with experience in technical education development, to lead a new Customer Service & Support (CSS) Technical Skilling team. The team has two focus areas: content portfolio management and content development. The Technical Skilling team leader will oversee the both the portfolio management and executive rhythm of the business with CSS stakeholders and leaders, as well as a newly formed CSS technical content development team that designs, creates and maintains curriculum paths for Microsoft support engineers supporting customers with Azure, Microsoft 365, and Business Applications scenarios.  


Key responsibilities include: 

  • Stakeholder AlignmentOversee the skilling rhythm of business bringing CSS, Engineering, DevRel and WWL executives together to prioritize, align and discuss the technical, professional, and onboarding programs and curriculum for support engineers 
  • Technical Curriculum Portfolio StrategyNurture the vision and roadmap for Microsoft’s technical skilling curriculum and assessment portfolio, using a consistent, data-informed and customer-obsessed framework to evolve the portfolio across each of CSS’s Strategic Business Units: Apps & Infra, DABA (Data & AI and Business Applications), and Modern Work.  
  • Technical Curriculum Content DevelopmentCoach and support the CSS Technical Content Development team leader, whose mission is to improve and transform the way we develop technical curriculum for support engineers at Microsoft 
  • Employee Skilling Plan DevelopmentPartner with CSS as well as the Worldwide Learning Technical Skilling, Professional Skilling, and Manager & Compliance Skilling teams to lead the process for developing and approving the annual technical and professional employee skilling plans for support engineer roles 
  • Process Maturity & AlignmentDrive operational maturity in team processes, including work tracking, data & reporting insights; Partner with the WWL Solution Area and Services Portfolio Management leaders to identify opportunities for collaboration, alignment, and shared resources 
  • People Management & LeadershipModel, coach and care Microsoft and team values for team members; attract and retain diverse and inclusive talent 

The ideal candidate will have 10+ years of experience in disciplines such as learning & development, support readiness, product or program management. Regardless of your background, you should have the following skills: 

  • 7+ years of experience leading learning & developmentproduct, portfolio, or program management teams, with a proven track record of building and leading teams through growth and transformation 
  • Strong people management and coaching skills; commitment to Microsoft’s model, coach, care philosophy 
  • Strong interpersonal skills, cross-boundary collaboration skills, ability to lead with empathy, and demonstrate open and honest feedback and interactions 
  • Able to simplify complex ideas into easy to understand concepts for communications with colleagues and executives at all levels 
  • Able to rapidly gain/build trust and confidence of internal and external stakeholders 
  • Able to handle high-level, complex, ambiguous, and time-critical deadlines and deliverables across a broad range of topics 
  • Strong project management including Agile methodologies, continuous integration delivery mechanisms, experience in building ground up services & teams and ability to quickly spot and implement industry trends 
  • Deep understanding of Data (Data trends, content analysis, funnel trends) and fluency using Excel and other data reporting tools such as Power BI 
  • Experience defining and improving operational processes 
  • Deep familiarity with at least one Microsoft cloud platform technology (Azure, Microsoft 365, and/or Business Applications) 
  • A willingness to be agile, a motivated self-starter, and a passion to constantly learn and improve 
  • Experience working in a global, matrixed organization and working with cross-functional teams 
  • Exceptional Adaptability, Trusted Advisor, Executive Maturity, Collaboration, Customer Focus, Drive for Results, Influencing for Impact, and Judgment core competencies 
  • Competency in the following: Planning, Organizing, and Executing 
  • Works with high degree of Respect, Accountability, and Integrity 


Preferred qualifications: 

  • Deep understanding of Customer Service & Support readiness programs 
  • Technical training and exam industry experience 
  • Experience with agile development methodologies, and use of Azure DevOps to manage development priorities and backlogs 
  • Ability to travel domestically and internationally (when business travel resumes; 10-15%) 


Microsoft is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.  We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. If you need assistance and/or a reasonable accommodation due to a disability during the application or the recruiting process, please send a request via the Accommodation request form.


Benefits/perks listed below may vary depending on the nature of your employment with Microsoft and the country where you work.

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CSS Technical Skilling Director
Microsoft Corporation