Sales Director - IT Managed Services

The Sales Director - IT Managed Services, is responsible for driving revenue growth by selling managed services offerings to small and midmarket and/or enterprise clients. This role owns the full sales cycle-prospecting, discovery, solution positioning, proposal development, and close-while partnering with managed services leadership to support gotomarket strategy, product positioning, and client engagement.

Key Responsibilities

• Full-cycle sales ownership: Generate, qualify, and close opportunities through the full sales cycle; build and maintain a healthy pipeline of prospects.
• Solution-based selling: Apply an indepth understanding of managed services offerings to address complex and strategic IT needs within client organizations.
• Relationship development: Discover, develop, and manage business relationships with prospects and customers; lead or participate in account strategy sessions.
• Executive communication: Create and deliver presentations and proposals to "C" level stakeholders; clearly communicate key benefits and positioning of our managed services.
• Customer discovery & insight: Provide accurate insight into a prospect's strategic initiatives and buying readiness; map services to business outcomes and priorities.
• Respond to inbound demand: Respond to existing and prospective client requests for managed services and coordinate internal resources to move opportunities forward.
• Microsoft partner alignment: Collaborate with Microsoft as a strategic technology partner and represent the company's capabilities and service offerings effectively in the Microsoft ecosystem

Qualifications (Required)

• Proven success selling IT managed services with a demonstrated ability to meet/exceed sales targets.
• Demonstrated track record of selling managed services to small and midmarket businesses (or similar client base aligned to your organization).
• Strong understanding of IT operations and infrastructure concepts to support credible discovery and solution conversations.
• Ability to lead consultative discovery, position value, and progress opportunities from initial contact to close (full-cycle).
• Strong executive presence and communication skills, including proposal/presentation development and delivery.

Preferred Qualifications

• Experience selling Microsoft-aligned services such as Microsoft 365/O365, Azure, SharePoint, SQL, and related managed services.
• Experience working with or within a Microsoft Solutions Partner environment and partnering alongside Microsoft.

Success Measures

• Pipeline creation and coverage (new qualified opportunities, pipeline velocity)
• Win rate and average deal size for managed services agreements
• Attainment vs. quota / sales targets
• Executive meeting volume and proposal activity (Clevel presentations delivered)
• Renewal/expansion growth in managed services accounts (if role includes farming)

Why Oakwood:

Oakwood Systems Group brings over 40 years of transformation leadership, multiple Microsoft Partner of the Year awards, and a growing portfolio of AIled and securityfirst solutions. Enterprise Sales Directors at Oakwood are empowered to lead with insight, innovate with Microsoft, and build longterm client partnerships that matter.