DescriptionIndustry Focus: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.
AI-
Enabled Sales Expectations: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.
Responsibilities:- 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
Key Requirements:- 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
Why Oakwood: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.
