Sr. Sales Director; IT Managed Services

Oakwood Systems Group is seeking a proven managed services seller who can open doors, lead executive‑level discovery, and convert complex technology needs into long‑term client partnerships. This is a hands‑on, full‑cycle sales role for a strategic hunter who wants the autonomy to build a market, the credibility of a Microsoft‑aligned portfolio, and direct access to technical and managed services leaders throughout the sales process.

You will lead with business outcomes, not product pitches. Your focus will be net‑new and expansion recurring revenue across SMB's, supported by project and advisory services that can create an entry point and accelerate broader managed services adoption.

Ownership and visibility: Build and execute your territory strategy while influencing Oakwood's managed services go‑to‑market approach.

Executive access: Engage CIOs, CISOs, IT leaders, and business executives around operational resilience, security, cost, risk, and modernization.

Microsoft‑centered differentiation: Take a broad portfolio to market across Azure, Microsoft 365, Modern Work, Security, data platforms, applications, and cloud operations.

Collaborative selling: Partner with managed services leadership, solution architects, delivery leaders, marketing, and Microsoft to build credible, outcome‑focused solutions.

Long‑term value creation: Win durable client relationships through recurring services, renewals, expansion, and cross‑sell opportunities.

Own the full sales cycle: Prospect, qualify, discover, solution, propose, negotiate, and close net‑new managed services opportunities.

Build predictable pipeline: Create and maintain a healthy pipeline through targeted outbound activity, referrals, strategic networking, partner relationships, events, and disciplined follow‑up.

Lead consultative discovery: Uncover operational pain points, service gaps, security exposure, reliability concerns, modernization priorities, and buying readiness.

Position business value: Translate Oakwood's capabilities into measurable outcomes such as improved service quality, stronger security, reduced operational burden, better user experience, and greater technology scalability.

Navigate complex buying groups: Build relationships across executive, technical, procurement, finance, and operational stakeholders while maintaining momentum and commercial alignment.

Orchestrate internal experts: Bring the right technical and delivery leaders into pursuits, establish clear next steps, and maintain ownership of the client and commercial conversation.

Develop compelling proposals: Create and deliver executive presentations, proposals, statements of work, pricing narratives, and business cases that clearly differentiate Oakwood.

Forecast with discipline: Maintain accurate CRM activity, opportunity stages, close plans, risks, next steps, and revenue forecasts.

Grow strategic accounts: Identify expansion, renewal, and cross‑sell opportunities that deepen client value and increase recurring revenue.

Shape the market: Share client insights, competitive intelligence, and field feedback to strengthen offerings, messaging, sales tools, and go‑to‑market strategy.

• Managed cloud and infrastructure operations, including Azure and hybrid environments
• Managed Microsoft 365, endpoint, collaboration, and end‑user services
• Managed security, monitoring, response, and compliance support
• Managed data, platform, application, and performance services
• Service desk, support, and related Microsoft‑aligned operational services

A demonstrated record of meeting or exceeding quota while selling IT managed services, recurring‑revenue solutions, or complex technology services.

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