Strategic MSP Sales Director: Microsoft Cloud & Security

Oakwood Systems Group Inc.; Kansas City (MO); On-site; USD 90,000 - 130,000; Full time

Job summary

Oakwood Systems Group in Kansas City is seeking a proven managed services seller to 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.

Qualifications

• Proven record selling IT managed services or complex technology services.
• Experience winning net-new logos and building pipelines.
• Ability to engage CIOs, CISOs, IT leaders, and executives.
• Fluency in managed services economics including MRR/ARR, renewals, and expansions.
• Knowledge of Microsoft ecosystem (Azure, M365) is a plus.

Responsibilities

• Own the full sales cycle: prospect, qualify, discover, solution, propose, negotiate, and close.
• Build a healthy pipeline through outbound activity, referrals, networking, and partner relationships.
• Lead consultative discovery to uncover pain points, gaps, security exposure, and modernization priorities.
• Position Oakwood's capabilities to deliver measurable outcomes and value.
• Navigate complex buying groups across executive, technical, procurement, and finance stakeholders.
• Orchestrate internal experts and drive next steps while owning the client and commercial conversation.
• Develop compelling proposals, executive presentations, and business cases that differentiate Oakwood.
• Forecast with discipline using CRM, stages, risks, and revenue plans.
• Grow strategic accounts through renewals, expansions, and cross-sell opportunities.
• Shape the market with client insights and competitive intelligence.

Skills

Executive selling

MS solutions

Strategic hunting

Pipeline development

Executive stakeholder engagement

Job description

Oakwood Systems Group in Kansas City is seeking a proven managed services seller to 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.