Enterprise Sales Director

Oakwood is a Microsoft Solutions Partner with designations in Data & AI, Digital & App Innovation, Infrastructure, Modern Work, and Security. We have also achieved advanced specializations in AI applications and deliver Microsoft‑certified support services, reinforcing our position as a trusted, end‑to‑end Microsoft partner. This depth allows our Enterprise Sales Directors to lead with credibility, differentiation, and measurable client impact.

The Enterprise Sales Director will prioritize and develop deep expertise within one or more of the following verticals:

• Manufacturing – smart factory initiatives, ERP modernization, data platforms, AI‑enabled operations, security and resilience
• Health Care – data interoperability, analytics, AI‑assisted insights, secure collaboration, regulatory‑aligned cloud architectures
• Higher Education – modern campus solutions, data and AI for student success, secure digital learning environments, IT modernization

Success requires understanding industry‑specific business models, regulatory pressures, and transformation priorities, and aligning Oakwood and Microsoft solutions accordingly.

Enterprise Sales Directors are expected to be proficient in leveraging AI capabilities to improve sales effectiveness and client outcomes, including:

• AI‑driven prospecting
  : using AI tools and sales intelligence platforms to identify ideal customer profiles, buying signals, and whitespace opportunities
• Relationship development
  : applying AI insights to personalize outreach, improve executive conversations, and strengthen long‑term account relationships
• Client strategic awareness
  : leveraging AI to synthesize client data, market trends, and Microsoft roadmaps to proactively guide customer strategy

This role embraces AI not as a future concept, but as a daily productivity and insight engine across the full sales lifecycle.

• Generate, qualify, and close opportunities across the full sales cycle with a focus on complex, multi‑solution engagements
• Apply deep understanding of Oakwood’s service lines—Managed Services, App Modernization, Data & AI, Modern Work, Intelligent Infrastructure—to solve enterprise‑level business challenges
• Build and maintain a high‑quality pipeline through targeted industry outreach, account planning, and Microsoft co‑sell motions
• Lead discovery and strategy sessions with prospective and existing customers, identifying pain points and mapping solutions to business outcomes
• Develop and present executive‑level proposals that align Oakwood and Microsoft capabilities to customer strategic initiatives
• Meet or exceed an annual sales target of $2M–$4M through new logo acquisition and account expansion
• Maintain high levels of customer satisfaction, responsiveness, and retention while identifying follow‑on opportunities
• Actively engage in demand‑generation activities using digital channels, social platforms, and AI‑enabled marketing and sales tools

• 7+ years of experience in consultative enterprise technology sales, preferably within Manufacturing, Health Care, or Higher Education
• Proven success meeting or exceeding quota through disciplined pipeline management and strategic selling
• Strong understanding of Cloud (IaaS, PaaS, SaaS), Agentic AI Development, Data & AI, Security, and Modern Work solutions
• Demonstrated ability to leverage AI‑powered sales tools, CRM platforms, and data insights to improve outcomes
• Executive‑level communication skills with the ability to build trust and credibility across technical and business stakeholders
• Strategic mindset with the ability to align technology investments to end‑to‑end business models
• Commitment to continuous professional development and staying current with Microsoft technologies and partner programs
• High drive, adaptability, and passion for winning

Oakwood Systems Group brings over 40 years of transformation leadership, multiple Microsoft Partner of the Year awards, and a growing portfolio of AI‑led and security‑first solutions. Enterprise Sales Directors at Oakwood are empowered to lead with insight, innovate with Microsoft, and build long‑term client partnerships that matter.