Director, Digital Portfolio Management & Chief of Staff

The Leading Hotels of the World • New York, NY

14d • $165,000 - $190,000 • Hybrid

About The Position

The Leading Hotels of the World is seeking a Director, Digital Portfolio Management & Chief of Staff to serve as a strategic and operational leader within our Digital organization. Partnering closely with the Chief Digital Officer and Digital leadership team, this role will help translate strategy into coordinated priorities, investment decisions, and measurable execution.
The Director will lead Digital portfolio management and governance, executive operations, strategic planning, performance management, and cross-functional coordination. By bringing together portfolio, delivery, financial, resource, and performance insights, this role will provide the visibility and decision support needed to manage Digital investments and maximize their value.
Working across Digital Experience, Platform Strategy, Solutions & Delivery, Digital Operations, Data, IT, Finance, and business teams, the Director will help connect strategy, investment, execution, and performance while supporting an effective, high-performing Digital organization.
This is a full-time position located in New York City. We offer flexible workplace policies that allow for working remotely 3 days a week and require being in our NYC office 2 days a week (Wednesdays and Thursdays).

Requirements

• 10+ years of progressive experience in enterprise portfolio management, PMO leadership, strategic planning, business operations, project or program governance, Digital transformation, consulting, or related leadership roles.
• Demonstrated experience leading enterprise or function-wide portfolio governance, investment planning, strategic initiatives, or complex cross-functional programs in matrixed organizations.
• Experience partnering directly with executive and senior leadership on strategic planning, investment decisions, governance, organizational effectiveness, and execution.
• Strong portfolio, program, and delivery leadership capabilities, including translating strategy into priorities, governance mechanisms, operating plans, and measurable outcomes.
• Strong analytical and financial acumen, with experience in executive reporting, performance measurement, resource planning, financial planning, investment analysis, and budget coordination.
• Ability to synthesize complex portfolio, financial, delivery, and performance information into clear executive recommendations, presentations, and decision materials.
• Demonstrated ability to navigate competing priorities, risks, dependencies, and resource constraints while facilitating complex decisions, influencing senior stakeholders, and aligning cross-functional teams.
• Experience building or maturing portfolio management, governance, project delivery, performance management, or business operations capabilities and leading organizational change.
• People leadership experience, including coaching and developing professionals, setting priorities and performance expectations, and building high-performing teams.

Nice To Haves

• Experience supporting Digital, technology, customer experience, or transformation organizations preferred.
• Hospitality, travel, luxury, membership, or other customer-centric industry experience is a plus.

Responsibilities

• Lead governance and strategic planning for the Digital portfolio, ensuring investments are prioritized and sequenced based on enterprise priorities, business value, organizational capacity, and key dependencies.
• Own and evolve portfolio management practices, including intake, prioritization, investment planning, governance, performance visibility, and executive decision support.
• Provide leadership with an integrated view of portfolio health, investment priorities, delivery progress, risks, dependencies, resources, and performance.
• Guide portfolio-level trade-offs and recommendations across competing priorities to support informed investment, sequencing, and capacity decisions.
• Oversee governance and delivery coordination for high-priority Digital initiatives, establishing clear accountability, decision paths, escalation mechanisms, and executive visibility.
• Identify and help resolve strategic delivery risks, cross-functional dependencies, resource constraints, and organizational issues affecting portfolio outcomes.
• Strengthen project and portfolio management practices to improve delivery predictability, accountability, and organizational delivery maturity.
• Establish performance management and executive reporting practices that measure portfolio performance, organizational effectiveness, investment progress, and business outcomes.
• Partner with Finance and Digital leadership on investment and budget planning, providing portfolio-level visibility and coordination within a shared financial accountability model.
• Lead Digital business operations and organizational planning, including resource and capacity planning, operating priorities, leadership planning cycles, and cross-functional commitments.
• Translate portfolio, delivery, financial, and performance information into executive insights and recommendations that support planning, investment decisions, and portfolio optimization.
• Serve as the Chief Digital Officer’s operational partner, leading executive operating rhythms, governance forums, leadership reviews, and management practices.
• Support Digital strategic planning and executive communications through clear narratives, recommendations, presentations, and decision materials.
• Coordinate cross-functional decision-making and executive forums, ensuring decisions, accountabilities, dependencies, and follow-through are clearly established.
• Serve as a trusted advisor to Digital leadership on organizational priorities, execution challenges, operating-model evolution, and opportunities to strengthen Digital capabilities.
• Build strong partnerships across Digital, Data, IT, Finance, and business leadership to align priorities, address enterprise dependencies, and enable execution of Digital strategy.
• Drive continuous improvement across Digital governance, portfolio management, business operations, and performance management to strengthen transparency, accountability, efficiency, and organizational effectiveness.
• Lead, coach, and develop portfolio, project management, and performance management professionals, establishing clear expectations, priorities, and accountability.
• Build team and organizational capability through coaching, feedback, professional development, succession planning, and scalable management practices.
• Empower team members to lead effectively across complex, cross-functional initiatives while maintaining appropriate governance and executive visibility.
• Foster an inclusive, collaborative, high-performing culture grounded in ownership, transparency, continuous learning, and shared accountability.

Benefits

• 27 days of Paid Time Off (PTO)
• 11 paid holidays, including birthdays as a floating holiday
• Medical coverage available within the first month
• Health Savings Account (HSA) with Company contribution
• 401(k) company match up to 4% of salary
• Up to $500 for home office setup credit
• Up to $500 travel credit that supports and encourages our employees’ passion for travel
• Unlimited access to financial advisors
• Collaborative and inclusive work environment

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed