Principal Digital Solution Specialists

Do you enjoy working on a high-performing, fast-paced sales team? Are you insatiably curious and do you lean into uncertainty, take risks, and learn quickly from your mistakes? If so, we are looking for you!    

At Small Medium Enterprises and Channel (SME&C), we are leading a high-growth, AI-powered global sales team—one that is deeply connected to our partners and driven by customer success. By uniting our Small Medium Business, Corporate, Strategy, and Partner teams, we are unlocking the largest customer opportunity, backed by the industry’s most significant investments. Leveraging the power of AI and our extensive partner ecosystem, we are redefining how businesses of all sizes adopt technology to drive growth and innovation.   

SME&C is more than a sales organization—it’s a culture of innovation, opportunity, and inclusivity. Here, you’ll be part of a diverse, high-performing, and customer-obsessed team where collaboration, connection, and continuous learning fuel everything we do. If you thrive in a fast-paced, digital-first environment and are eager to make a meaningful impact, explore how SME&C can be the next step in your career. Together, we are shaping the future of business.    

As a Principal Digital Solution Specialist – AI Workforce, you will lead the Microsoft 365 Copilot and Copilot Cowork strategy for the Sales Unit’s most strategic and complex customers. You will engage senior business and technology leaders to reimagine how work gets done—from assisting employees in the flow of work with Copilot to delegating complex, multi-step tasks through Cowork and scaling repeatable business processes with agents. 

You will lead high-value customer engagements, develop compelling transformation and commercial strategies, and orchestrate Microsoft teams and partners to win complex opportunities. You will connect AI-powered productivity, agentic work, responsible AI, security, governance, adoption, and change management into a clear customer value proposition. 

We are looking for a high-impact specialist seller with strong executive presence, commercial leadership, and sufficient technical credibility to lead sophisticated AI Workforce conversations. The successful candidate will be able to challenge customer thinking, build business cases, navigate competitive pursuits, and establish trust with business, technology, security, finance, and procurement stakeholders. 

You will lead consultative customer conversations and collaborate on the planning, orchestration and execution of end-to-end AI Workforce solutions opportunities with internal stakeholders and partners to cross-sell and up-sell. This opportunity will allow you to learn and accelerate your career growth, honing your solution sales and collaboration skills, and deepening your AI Workforce end-to-end expertise. This role is flexible in that you can work up to 50% from home. 

Microsoft’s mission is to empower every person and every organization on the planet to achieve more. As employees we come together with a growth mindset, innovate to empower others, and collaborate to realize our shared goals. Each day we build on our values of respect, integrity, and accountability to create a culture of inclusion where everyone can thrive at work and beyond.  

• Sales Excellence 

• • Builds and transforms new markets by leveraging technical and industry expertise, partners, and resources; leads a team to explore business and emerging opportunities to optimize the portfolio and facilitate customer innovation.
  • Reviews feedback report and sets long-term strategies aimed at maintaining levels of client satisfaction; coaches others on ensuring customer/partner satisfaction and decreasing dissatisfaction by establishing recovery action plans to improve clients' overall experience; manages and/or orchestrates sales and delivery success through the account team and pursuit team.
  • Engages with internal and external stakeholders on business planning, rhythm-of-business (ROB) meetings to review and plan for strategic accounts across territories.
  • Collaborates with extended sales team, partners, and marketing to lead business analysis (e.g., whitespace analysis, identify industry trends) to pursue high-potential customers and develop a target list of potential business; acts as a thought leader and validates opinions and perspectives from business analysis.
  • Manages the end-to-end business for strategic accounts across the organization; leads forecasting for accounts and develops a portfolio and territory plan to drive intentional selling with on-strategy engagements in high propensity accounts; mentors less experienced team members.
  • Completes required training and obtains relevant product and role certifications aligned to the role and workload/industry; proactively seeks training, including information that adds to the understanding of customers' business, and shares it with team members.

• Sales Execution & Compete 

• • Proactively builds external stakeholder network and leverages internal partners to engage external stakeholders; acts as a thought leader and subject matter advisor to the executive-level business decision makers at the customer's/ partner's business; guides others on identifying and engaging decision makers and stakeholders to expand the relationship with customers/ partners.
  • Explores and assesses the needs of strategic/high-potential customers; articulates business value and long-term implications for customer business; collaborates with internal teams, partners, and services to lead the proposal or development of solutions that align with customer and Microsoft priorities; analyzes market trends to identify opportunities for new solutions.
  • Develops strategies for driving and closing strategic and/or prioritized opportunities; collaborates with account teams to ensure alignment with the account strategy and plan; leads deal execution with the deal teams across the organization; coaches others on the implementation of close plans (e.g., how to map timeline, engage the customer, get customer buy in and commitment) to de-risk and drive predictable deal closure.
  • Brings impactful industry insights into customer engagements and closes deals with customers; acts as a thought leader across solution areas to advise customers across business functions on digital transformation with a challenger mindset that accounts for customers' business needs and priorities; leads virtual transformational shifts to drive deployment and create business value for customers; may lead partner integration into account/territory planning and customer engagements.
  • Orchestrates with team members on conducting personal campaigns to discover new opportunities and generate new leads; leads conversations with strategic/high-potential customers (e.g., high-budget, global-account, highly competitive) along with account teams or partners; facilitates the account team unit (ATU) to build pipeline in collaboration with partners and services; guides others on social selling; applies Microsoft's sales process (MSP) to determine the quality of the opportunity and whether to proceed, and educate the customers on how to best address their needs.
  • Drives consumption and grow business with existing strategic customers by initiating conversations, guiding others on demos or quotes, and the collaboration with partners or internal teams (e.g., Technical Sales Professionals, global black belts [GBBs]); for licensing transactions and project engagements, ensures rapid and robust deployment plan at point of sale that is validated by services and partners; identifies, articulates, and facilitates the removal of blockers to consumption by partnering with internal and external stakeholders.

• Field Multiplier & Coaching 
• Create and share compete playbooks, executive talk tracks, and discovery guides; co-sell with Digital Solution Specialists (DSS) and partners to strengthen overall team capability. 
• Provide real-time coaching during high-value engagements and deliver actionable post-engagement feedback to raise execution quality. 
• Scale field capability through enablement on competitive scenarios and emerging security trends. 
• Build mindshare through thought leadership and industry presence. 
• Scaling and Collaboration

• • Leads the sales orchestration to proactively drive deal closure by identifying and aligning internal stakeholders as well as leveraging and expanding relationships with partners; applies a holistic approach to build network across territories; positions opportunities to promote collaboration and participation.
  • Leads the planning and execution on opportunities with resources and partners to cross-sell, up-sell, and co-sell; identifies, leverages, coordinates partners and resources across solution areas, and supports on-boarding new partners; validates partner solution relevance for customers; provides input and feedback to Partner Team on developing partner strategies and consumption plans, and connects the partner ecosystems to scale business results.

• Growth Mindset 
• Bring impactful industry insights, market perspective, and threat intelligence into customer engagements. 
• Demonstrate a commitment to continuous learning in cybersecurity and foster innovation within the team. 

Required/minimum qualifications

• Bachelor's Degree in Computer Science, Information Technology, Business Administration, or related field AND 7+ years of technology-related sales or account management experience OR 9+ years of technology-related sales or account management experience.

Additional or preferred qualifications

• Master's Degree in Business Administration (e.g., MBA), Information Technology, or related field AND 8+ years of technology-related sales or account management experience OR Bachelor's Degree in Information Technology, or related field AND 10+ years of technology-related sales or account management experience OR 11+ years of technology-related sales or account management experience.

This position will be open for a minimum of 5 days, with applications accepted on an ongoing basis until the position is filled.

Microsoft is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, citizenship, color, family or medical care leave, gender identity or expression, genetic information, immigration status, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran or military status, race, ethnicity, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable local laws, regulations and ordinances. If you need assistance with religious accommodations and/or a reasonable accommodation due to a disability during the application process, read more about requesting accommodations.