Tobi Osinowo, MBA, PMP, SAFe
Senior Manager in Digital Delivery @ Hilton
About
Results-driven Senior program and digital delivery leader with experience owning complex, enterprise-scale initiatives across regulated and consumer-facing environments. Proven ability to partner with executive stakeholders to translate business strategy into structured, on-time execution across defense, consulting, and global hospitality organizations. Brings strength in leading cross-functional teams across product, engineering, operations, and external partners to deliver customer-facing platforms, core digital capabilities, and large-scale transformation initiatives. Known for balancing delivery speed, governance, and quality while managing multimillion-dollar programs and mission-critical systems. Consistently delivers measurable outcomes, including revenue growth, cost reductions, faster time-to-market, and improved delivery discipline through Agile and SAFe frameworks. MBA with PMP and SAFe certifications. Interested in senior program, digital delivery, and transformation leadership roles where execution excellence and business outcomes are critical.
United States
Dallas
Management Consulting
Proposal Writing, Business Transformation, Databases, Operational Planning, Data Centers, Project, Agile Project Management, Consulting, Troubleshooting, Call Centers, Software Documentation, Credit, Research, Engineering, Project Management, Strategic Planning, SAP Implementation, Continuous Improvement, Quality Assurance, Risk Management
Experience

Senior Manager in Digital Delivery
Led end-to-end digital delivery for enterprise web and mobile initiatives, supporting global hospitality platforms, achieving 100% on-time execution across 5+ major releases annually. Directed cross-functional teams of 25+ members across product, engineering, UX, QA, and vendors, delivering customer-facing capabilities at scale that improved guest engagement metrics by 15–20%. Implemented Agile and SAFe delivery practices, increasing sprint throughput by 30% and improving release cadence, resulting in faster time-to-market for key digital initiatives. Managed multimillion-dollar vendor and partner engagements, driving contract-level accountability and 10% cost optimization while ensuring quality and timeline adherence. Proactively identified and mitigated delivery risks and dependencies, reducing project delays by 25% and strengthening stakeholder confidence through enhanced reporting and transparency.

Senior Program Manager
Dallas, Texas, United States
Led and governed multiple complex, cross-functional technical programs using Agile and Scrum frameworks, consistently delivering on schedule and exceeding program success benchmarks by 25%. Directed high-visibility, contracted initiatives, managing integrated schedules, resource allocation, and execution governance, resulting in early delivery across multiple programs. Optimized program material strategies and strengthened coordination across Program Management, Engineering, Integrated Product Teams (IPTs), and Product stakeholders, driving a 20% reduction in supply chain and materials costs. Established structured problem-scoping and decision frameworks, accelerating executive decision-making and reducing program delays by 30% through clear issue definition and stakeholder alignment. Served as Program Management lead for a $100M materials portfolio, applying Agile delivery and continuous improvement practices to enable timely deployment of mission-critical installations supporting military assets.

Senior Consultant/Senior Program Manager
California, United States
Led end-to-end delivery of customer-facing subscription platform enhancements on PlayStation, driving a 25% increase in monthly recurring revenue and 15% growth in user base through a tiered subscription model. Partnered with senior business leaders, product managers, and engineering teams to define and launch high-impact subscription capabilities, improving monetization, attribution, and long-term platform growth. Directed Agile and Scrum-based technical initiatives from concept through launch, aligning operations, engineering, and product teams to prioritize and execute growth-focused roadmap initiatives. Led a Salesforce transformation program, building executive-level business cases that accelerated time-to-value, generated $400K in annual cost savings, and reduced average customer call handling time by 4%. Identified and closed functional and technical delivery gaps, providing data-driven recommendations that accelerated delivery timelines and enabled early completion of analytics dashboards by one month.

Project/Program Manager
Dallas/Fort Worth Area
Led portfolio-level Agile planning and prioritization, aligning global business initiatives to accelerate solution development, streamline workflows, and increase operational efficiency by 35%. Directed a high-impact Sprint program leveraging an enterprise CRM platform, orchestrating cross-functional resources to deliver outcomes that generated $70M in net profit while meeting aggressive deadlines. Designed and deployed a performance analytics framework, analyzing 120 metrics across 4 procurement processes, introducing 30 new KPIs, and implementing real-time dashboards to close visibility gaps and enable data-driven decision-making. Guided teams in disciplined Agile delivery, overseeing backlog curation, estimation, and execution standards, resulting in a 35% reduction in development cycle time. Led end-to-end Scrum delivery for an internally developed quality management platform, establishing it as the system of record for part compliance for 350+ users across 20 teams, while ensuring regulatory compliance and operational efficiency.
Tobi Osinowo, MBA, PMP, SAFe's Contact Information
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