[Hiring] Engagement Manager @Oakwood Systems Group Inc.

Role Description

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.

Qualifications

• 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.

Requirements

• 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.