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 mid‑market 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 go‑to‑market 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 in‑depth 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 mid‑market 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 (C‑level 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 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.