7+ years in consultative enterprise technology sales, especially in Manufacturing, Health Care, or Higher Education
Track record of meeting/exceeding sales quotas through disciplined pipeline management
In-depth knowledge of Cloud (IaaS, PaaS, SaaS), AI development, Data, Security, and Modern Work solutions
Ability to leverage AI-driven sales tools and CRM for enhanced outcomes
Exceptional executive communication skills to connect with technical and business leaders
Strategic thinker capable of aligning tech investments with business models
Commitment to ongoing professional growth and proficiency in Microsoft technologies
Responsibilities
Generate, qualify, and close complex, multi-solution sales opportunities
Utilize deep knowledge of Oakwood's services to address enterprise-level challenges
Build and maintain a sales pipeline through targeted outreach and Microsoft collaboration
Conduct strategy sessions to identify customer pain points and map solutions
Deliver executive-level proposals aligning Oakwood and Microsoft offerings with customer initiatives
Achieve annual sales targets of $2M-$4M through new and existing accounts
Drive customer satisfaction and retention while spotting new opportunities
Engage in digital demand generation using AI-enabled marketing tools
Benefits
Comprehensive health and wellness programs
Flexible working hours and remote work options
Professional development opportunities through training and certifications
Collaborative and innovative team environment
Access to cutting-edge technology and resources
Employee recognition programs
Generous time-off policies and parental leave
Full Job Description
Description
Industry 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
