Sr. Director, Strategy & Planning

Sysco

2d•Remote

About The Position

The Senior Director, Strategy & Planning (Americas) is a highly strategic and execution-focused role that exists to amplify the impact of the VP by driving alignment, prioritization, and operational efficiency across the organization. Acting as a trusted advisor and integrator, this position ensures that the VP's vision and priorities are translated into actionable plans, executed effectively, and communicated clearly across stakeholders. The role is responsible for managing the VP's operating cadence, facilitating decision-making, coordinating cross-functional initiatives, and overseeing critical communications and strategic deliverables. Success in this role requires a strong mix of business acumen, organizational savvy, and the ability to navigate complexity while maintaining focus on outcomes.

Requirements

8–12 years of progressive experience in technology within large, matrixed organizations
Proven experience supporting senior executives or working in highly visible roles requiring discretion, sound judgment, and influence
Strong track record of leading cross-functional initiatives and aligning diverse teams to deliver complex programs
Familiarity with IT planning, financial management, and governance processes, including budgeting cycles, investment reviews, and performance tracking.
Demonstrated ability to craft high-quality executive-level communications and strategic deliverables including preparation of board materials, leadership presentations, and organizational messaging.
Experience with IT sourcing and vendor management, including contract review, vendor performance tracking, and alignment with service-level expectations.
Exposure to M&A integration and organizational change, particularly aligning technology teams, roadmaps, or platforms post-acquisition.
Experience operating in global or multi-regional environments, coordinating across time zones, cultures, and business models
Executive Communications – Expertise in crafting high-quality presentations, board materials, and strategic communications using tools like PowerPoint and Word, with a strong emphasis on clarity, simplicity, storytelling, and stakeholder alignment.
IT Financial Acumen – Understanding of IT budgeting, forecasting, cost allocation models (e.g., gross/net), and financial performance metrics.
Contract Review & Vendor Coordination – Ability to review and interpret technology contracts, statements of work, and service-level agreements, coordinating with procurement, legal, and vendor management teams to ensure alignment with strategic goals, budget constraints, and compliance requirements.
Strategic Planning Tools – Proficiency in tools and methodologies for enterprise planning, portfolio management, and prioritization frameworks (e.g., OKRs, balanced scorecards, strategic roadmaps).
Project & Program Management – Skilled in managing complex, cross-functional initiatives using agile, waterfall, or hybrid delivery methods; familiarity with tools like Planview and Smartsheet.
Technology Fluency – Strong understanding of core IT functions (e.g., infrastructure, applications, cybersecurity, data, architecture) and how they enable business outcomes.
Data Analysis & Reporting – Ability to interpret and synthesize data into actionable insights, proficiency with Excel, Power BI, or other analytics and dashboard tools.
Collaboration Platforms – Proficiency in enterprise collaboration tools (e.g., Microsoft 365, Teams, SharePoint, Confluence) to manage workflows and drive team coordination.
Fluency in English
Reasonable accommodations will be made to enable individuals with disabilities to perform the essential functions of this job.
Standard office-based work demands

Nice To Haves

Led technology strategy development at the enterprise or business unit level, including translating vision into actionable roadmaps.
Worked in a high-growth, post-acquisition, or restructuring environment, helping stabilize operations or integrate teams
Partnered with enterprise functions such as Legal, Finance, or HR on strategic initiatives beyond day-to-day coordination — e.g., designing new governance models, building business cases, or developing workforce plans.
Supported or prepared content for investor relations, board technology briefings, or external executive communications.
Built or matured an office of the VP function, including implementing KPIs, leadership cadences, and initiative tracking frameworks.
Certifications in project management (PMP), business relationship management (BRMP), change management (CCMP)

Responsibilities

Strategic Planning & Prioritization – Drive alignment around the VP’s priorities, orchestrate annual and quarterly planning cycles, and ensure focus on the most critical initiatives across the technology organization.
Executive Decision Support – Provide analysis, context, and recommendations to support effective and timely decision-making by the VP and their leadership team.
Operating Rhythm & Governance – Manage the VP’s calendar of business reviews, staff meetings, leadership forums, and ELT engagements; ensure agendas are focused, materials are high quality, and outcomes are actionable.
Cross-Functional Program Execution – Lead or support the execution of team-wide technology initiatives, ensuring accountability, coordination, and progress tracking.
Internal Communications & Messaging – Develop executive-level communications, presentations, and messaging to align stakeholders and reinforce key strategic narratives across the organization.
Metrics, Reporting & Insights – Oversee development of dashboards and performance indicators that provide visibility into organizational health, progress on key initiatives, and operational risks.
Special Projects & Confidential Initiatives – Serve as a go-to leader for high-priority, time-sensitive efforts requiring discretion, judgment, and broad organizational perspective.
Risk Awareness - Monitor emerging organizational or delivery risks, surface early indicators of misalignment or friction, and recommend proactive interventions to maintain strategic and operational momentum.