Oakwood Systems Group is a Microsoft Solutions Partner helping organizations transform how they work through cloud, data, AI, cybersecurity, modern workplace, and application solutions. We turn complex business challenges into practical roadmaps and measurable outcomes for an AI-driven future.

What You’ll Own

Project & Program Leadership

• Lead projects of varying size and complexity as well as coordinated programs with multiple workstreams, dependencies, stakeholders, and delivery teams.
• Apply disciplined project management practices across initiation, planning, execution, monitoring, control, and closeout.
• Build and maintain integrated plans, schedules, budgets, forecasts, RAID logs, decision logs, resource plans, governance cadences, and executive reporting.
• Use the right delivery approach for the work, including predictive, Agile, Scrum, hybrid, and iterative delivery models.
• Manage scope, quality, timelines, financial performance, risks, issues, changes, vendors, and cross-functional dependencies without losing sight of the client’s outcome.
• Create accountability across client and internal teams, remove obstacles, and escalate with clarity and sound judgment.

Technology Delivery

• Lead consulting engagements involving data platforms and analytics, artificial intelligence, custom software and application development, complex systems integration, cloud, and infrastructure.
• Partner closely with architects, engineers, developers, consultants, security specialists, and business stakeholders to translate solution designs into executable delivery plans.
• Demonstrate enough technical depth to challenge assumptions, identify delivery risk, connect dependencies, and communicate trade-offs credibly to both executives and delivery teams.
• Guide engagements through architecture, development, testing, deployment, adoption, transition, and value realization.

AI-Enabled Delivery Leadership

• Bring demonstrated experience using AI-enabled methods and tools, or a clear track record and commitment to becoming fully AI-enabled in how projects and programs are planned, managed, communicated, and improved.
• Use AI responsibly to accelerate planning, summarize and synthesize information, surface risks and dependencies, improve status reporting, support decision-making, and streamline delivery administration.
• Help clients identify practical opportunities for Microsoft Copilot, intelligent agents, workflow automation, and data-driven decision-making while aligning initiatives to business value, governance, security, and responsible AI expectations.
• Continuously test and adopt modern approaches that improve delivery speed, transparency, quality, and client outcomes.

Client Advisory & Executive Relationships

• Serve as the primary engagement leader and trusted advisor for strategic client relationships.
• Facilitate executive conversations that clarify objectives, resolve competing priorities, and connect technology investments to business outcomes.
• Lead steering committees, business reviews, discovery sessions, roadmap workshops, and executive briefings.
• Maintain client confidence through direct communication, transparent reporting, strong follow-through, and proactive risk management.
• Drive customer satisfaction, retention, referenceability, and long-term partnership.

Growth & Commercial Partnership

• Identify follow-on opportunities by listening to unmet needs, emerging risks, and adjacent business priorities.
• Partner with sales and practice leaders on account planning, proposals, statements of work, estimates, assumptions, and client presentations.
• Protect delivery integrity by ensuring proposed scope, staffing, timelines, dependencies, and commercial terms are realistic and clearly understood.
• Help clients build sequenced roadmaps that align business priorities, technology investments, organizational readiness, and measurable value.

What You Bring

Required

• 7+ years of progressive project, program, delivery, or engagement leadership experience in technology consulting, professional services, systems integration, or a comparable client-facing environment.
• Deep, demonstrated experience personally leading both projects and programs, including large or complex initiatives with multiple workstreams and executive visibility.
• Formal project management training and mastery of core tools and techniques. PMP certification is strongly preferred; comparable credentials and substantial demonstrated experience will be considered.
• Practical Agile training and delivery experience, such as Scrum, Kanban, SAFe, or hybrid methods, with the judgment to tailor the approach to the engagement.
• Demonstrated delivery experience across several of the following: data and analytics, AI, software/application development, complex integration, cloud, and infrastructure.
• Command of project and portfolio practices and tools used for planning, scheduling, financial management, risk and issue management, change control, governance, and reporting.
• Executive-level communication, facilitation, negotiation, presentation, and conflict-resolution skills.
• Ability to translate between business goals, technical decisions, delivery realities, and measurable value.
• A modern, AI-forward mindset supported by practical experience with AI-enabled work or a strong, demonstrable commitment to rapidly building that capability.

Highly Valued

• Experience leading within a Microsoft consulting partner, systems integrator, MSP, or professional services organization.
• Working experience with Microsoft Azure, Microsoft 365, Power Platform, Microsoft Fabric, Copilot, or related Microsoft cloud and AI solutions.
• Experience managing the development and evolution of a product, from discovery and roadmap through build, launch, adoption, and ongoing enhancement.
• Product management or product ownership experience, including backlog prioritization, customer discovery, outcome metrics, and coordination across engineering, design, sales, and go-to-market teams.
• Additional credentials such as PMI-ACP, Certified ScrumMaster, SAFe, Prosci, or relevant Microsoft certifications.

How Success Will Be Measured

• Projects and programs deliver against agreed outcomes, scope, quality, schedule, and financial expectations.
• Clients see you as both a rigorous delivery leader and a strategic advisor who makes complex work clearer and more achievable.
• Risks, dependencies, and decisions are surfaced early, managed actively, and communicated transparently.
• Executive stakeholders have confidence in the plan, the team, and the path to value.
• AI-enabled practices improve delivery efficiency, insight, communication, and decision quality.
• Strong execution and trusted relationships create repeat business, references, and expanded partnerships.
• Internal teams experience clear direction, strong collaboration, and decisive obstacle removal.

Why Oakwood

• Lead meaningful, high-visibility engagements at the center of cloud, data, AI, applications, and digital transformation.
• Work directly with executive leaders, innovative clients, and highly skilled consultants and architects across the Microsoft ecosystem.
• Help shape how modern, AI-enabled delivery is practiced, not simply follow an established playbook.
• Influence client strategy, delivery outcomes, account growth, and the continued evolution of Oakwood’s consulting capabilities.
• Join a culture that values curiosity, accountability, practical innovation, and measurable customer impact.