Sr. Sales Director (IT Managed Services)

Oakwood Systems Group Inc.•St. Louis, MO

19h

About The Position

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.

Requirements

A demonstrated record of meeting or exceeding quota while selling IT managed services, recurring-revenue solutions, or complex technology services.
Experience winning net-new logos and building pipelines, not solely managing an inherited book of business.
Success selling to organizations and engaging CIO, CISO, IT, operations, finance, and executive stakeholders.
Fluency in managed services economics and sales motions, including MRR/ARR, multiyear agreements, onboarding, service levels, renewals, expansions, and project-to-managed services conversion.
Working knowledge of IT operations, cloud, infrastructure, cybersecurity, Microsoft 365, Azure, and modern workplace concepts sufficient to lead to credible discovery.
Strong executive presence, commercial judgment, negotiation skills, and written and verbal communication.
A disciplined approach to account planning, qualification, pipeline management, CRM hygiene, forecasting, and close planning.
The ability to collaborate with technical experts without losing ownership of the business outcome or sales process.

Nice To Haves

Experience selling within a Microsoft Solutions Partner, MSP, cloud services, cybersecurity, or IT consulting environment.
Established relationships in target markets and a track record of converting those relationships into qualified opportunities.
Experience co-selling or partnering with Microsoft sellers, channel partners, referral partners, or technology alliances.
Familiarity with Microsoft Azure, Microsoft 365, Modern Work, Security, SharePoint, SQL, data platforms, AI, or related managed offerings.
Experience expanding managed services accounts through renewals, cross-sell, and adjacent project or advisory work.

Responsibilities

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.