Sr. Sales Director (IT Managed Services)

The Opportunity:

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.

WHAT MAKES THIS ROLE COMPELLING

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.

What You Will Do:

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 Services Portfolio:

Primary sales responsibility includes recurring services across:

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

What You Bring:

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.

Preferred Experience:

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.

How Success Will Be Measured:

Quota attainment and growth in new and expansion managed services revenue

Qualified pipeline creation, pipeline coverage, velocity, and forecast accuracy

Win rate, average contract value, sales-cycle progression, and quality of close plans

New logo acquisition and executive-level meeting activity

Proposal conversion, recurring-revenue mix, renewals, and account expansion

Quality of collaboration, client handoff, and alignment with delivery expectations

Why Oakwood:

Oakwood Systems Group is a Microsoft Solutions Partner delivering services across Application Development, Data & AI, Cloud Infrastructure, Modern Work, and Managed Services. We help organizations modernize technology environments and unlock business value through secure, scalable solutions aligned to the Microsoft ecosystem.

At Oakwood, senior sellers are empowered to lead with insight, collaborate directly with solution and delivery experts, and build client relationships that extend well beyond a single transaction. You will join a team that values accountability, curiosity, partnership, continuous learning, and measurable client impact.

Ready to build a market and a recurring revenue business with a Microsoft-focused team?

We want to meet you!