Senior Account Executive, Microsoft at WillowTree in Remote

WHO WE ARE Welcome to TELUS Digital, where innovation drives impact at a global scale. As an award-winning digital product consultancy and the digital division of TELUS, one of Canada’s largest telecommunications providers, we design and deliver transformative customer experiences through cutting-edge technology, agile thinking, and a people-first culture. With a global team across North America, South America, Central America, Europe, and APAC, we offer end-to-end expertise across eight core service areas: Digital Product Consulting, Digital Marketing Services, Data & AI, Strategy Consulting, Enterprise Technology, Enterprise Applications, Cloud Engineering, and QA & Test Engineering. From mobile apps and websites to voice UI, chatbots, AI, customer service, and in-store solutions, TELUS Digital enables seamless, trusted, and digitally powered experiences that meet customers wherever they are, all backed by the secure infrastructure and scale of our multi-billion-dollar parent company. LOCATION & FLEXIBILITY This role can operate remotely within the US (we are prioritizing candidates based on the US West Coast) OR be based out of one of our major US office locations - Charlottesville, VA, Durham, NC, Columbus, OH, or Boston, MA. THE OPPORTUNITY As Senior Account Executive for our Microsoft client account, you will serve as the primary commercial owner responsible for driving net-new revenue growth, white space development, and strategic expansion across one of our most valuable and complex client partnerships. This role will focus on account expansion, identifying and converting untapped opportunities within Microsoft, spanning their AI, Azure, Copilot, and broader machine learning teams. You will bring a sharp commercial instinct and proactive ability to translate Microsoft’s complex, large-scale data requirements into compelling, customized solutions that open new buyer relationships and expand our footprint into new teams and workstreams. Our service offerings span the breadth of what modern AI development demands. On the Generative AI https://www.telusdigital.com/solutions/data-for-ai-training/generative-ai side, we partner with clients to build human-aligned datasets for fine-tuning and evaluating large language models, supporting workflows including Supervised Fine-Tuning (SFT), Reinforcement Learning from Human Feedback (RLHF), red teaming, and bespoke dataset creation across more than 20 domains and 100 languages. For data collection https://www.telusdigital.com/solutions/data-for-ai-training/data-collection-services, we leverage a global AI Community of over one million contributors to deliver fully managed, multimodal datasets spanning text, audio, video, image, geo, and 3D data at any scale and complexity. Our data annotation https://www.telusdigital.com/solutions/data-for-ai-training/data-annotation-services capabilities transform raw, ambiguous data into contextually enriched training assets through advanced labeling services covering image and video, audio, text, and 3D sensor fusion. We also provide rigorous data validation https://www.telusdigital.com/solutions/data-for-ai-training/data-validation-services services, ensuring datasets are accurate, relevant, and production-ready through offerings such as search evaluation, ad evaluation, geo-location data verification, and machine translation quality assessment. Rounding out our portfolio, we offer a library of off-the-shelf datasets https://www.telusdigital.com/solutions/data-for-ai-training/off-the-shelf-data purpose-built for training and evaluating LLMs, computer vision models, and audio AI systems, providing clients with accessible, cost-effective solutions ready for immediate integration. The ideal candidate will bring both technical fluency and a sharp client-facing mindset, with the ability to translate Amazon's complex, large-scale data requirements into scalable, high-quality solutions that deliver measurable outcomes across their AI development initiatives. RESPONSIBILITIES White Space Development & New Business - Proactively map the Microsoft organization to identify untapped business units, emerging AI initiatives, and net-new buyer targets across Azure AI Services, Microsoft Copilot, Microsoft Research AI, and adjacent teams. - Develop and execute targeted outreach and pipeline development strategies to penetrate new buying centers within Microsoft that are not yet engaged with TELUS Digital. - Design and pitch custom solution concepts and prototype projects tailored to the specific data challenges and AI development priorities of new target buyers while using these as entry points to open and advance new commercial relationships. - Convert exploratory conversations into scoped pilots and prototype engagements that demonstrate value quickly and establish the foundation for larger, ongoing workstreams. - Build and maintain a robust pipeline of new logo opportunities within Microsoft, with clear stage progression and close plans. Client Account Ownership - Serve as the single-threaded commercial owner of the Microsoft account, responsible for retention, expansion, and net-new workstream growth across Microsoft’s AI and ML business units. - Build and maintain trusted relationships with AI, data science, product, and operations leaders with a particular focus on continuously expanding the network of buyers and influencers beyond existing contacts. - Lead strategic planning sessions and executive conversations that connect TELUS Digital’s capabilities to Microsoft’s evolving AI roadmap, surfacing new areas where bespoke solutions can deliver measurable impact. - Manage long-cycle renewals, expansions, and new statement-of-work negotiations across multiple business units and seniority levels. - Act as Microsoft’s internal advocate, surfacing insights that shape delivery execution, tooling priorities, and research investments. Data & AI Solutioning - Develop deep expertise across TELUS Digital’s Data for Generative AI, Data Collection, Data Annotation, Data Validation, and Off-the-Shelf Datasets capabilities, including text, image, video, audio, and sensor data labeling, agentic AI workflows, and responsible AI practices. - Lead the design of custom solution concepts and prototype project proposals for new and existing buyers, working closely with Solutions Architecture to ensure technical credibility and commercial viability. - Engage new target buyers with a consultative, insight-led approach while bringing a point of view on their data challenges before they have fully defined their requirements. - Stay ahead of industry trends in AI training data, including emerging labeling methodologies, quality assurance frameworks, and the evolving regulatory landscape around responsible AI, and use those insights to create timely, relevant hooks for new buyer engagement. Forecasting & Operations - Maintain rigorous pipeline hygiene, forecast accuracy, and account health reporting using Salesforce, with clear visibility into both existing account revenue and net-new opportunity development. - Collaborate cross-functionally with Delivery, Solutions Architecture, Finance, and Legal to structure prototype engagements and custom proposals that are both technically sound and commercially executable. Competencies - 7+ years of enterprise sales or strategic account management experience, with a demonstrated track record of new business development and white space conversion, not just account maintenance, within large, matrixed technology companies. - Experience selling to or within Microsoft is strongly preferred; familiarity with Microsoft’s organizational structure and buying processes is a meaningful advantage. - 3+ years of experience in Data Collection, Annotation, and/or Validation services, or adjacent AI/ML data services. - Proven ability to develop and pitch custom solutions and prototype concepts that resonate with new buyers who are earlier in their discovery process. - Deep familiarity with data workflows and quality frameworks across modalities, including text, image, video, audio, and sensor data, and a strong understanding of how training data supports AI model development and evaluation. - Comfort discussing generative AI, agentic AI pipelines, and responsible AI principles with both technical and business audiences. - Exceptional executive presence and communication skills, with the ability to engage credibly at the Director and VP level within a large, matrixed organization. - Proficiency with Salesforce and enterprise sales methodologies. - Blended hunter & farmer mindset balanced with consultative depth. Proactive, creative in solution design, and committed to understanding a buyer’s business before proposing a path forward. EQUAL OPPORTUNITY EMPLOYER At TELUS Digital, we are proud to be an equal opportunity employer and are committed to creating a diverse and inclusive workplace. All aspects of employment, including the decision to hire and promote, are based on applicants’ qualifications, merits, competence, and performance without regard to any characteristic related to diversity. We will only use the information you provide to process your application and to produce tracking statistics. Since we do not request personal data deemed sensitive, we ask you to abstain from sharing that information with us. For more information on how we use your information, see our Privacy Po https://www.telusdigital.com/privacy-policylicy