Vice President, Project Delivery (Technology)

Grand Circle • Boston, MA

16h • $220,000 - $250,000 • Hybrid

About The Position

Grand Circle Corporation is the leader in international travel, adventure and discovery for Americans aged 50+. Headquartered in Boston MA, and with more than 35 offices globally, more than two million Americans have traveled with our award-winning travel brands: Grand Circle Cruise Line, Overseas Adventure Travel and Grand Circle Travel. The VP of Project Delivery is a senior technology leader responsible for driving strategic execution across the enterprise by leading the portfolio of initiatives that fuel business growth, operational excellence, and digital transformation. The portfolio includes initiatives focused on engineering, ERP, data, marketing technology, infrastructure, and security. This role sets the governance, standards, and execution model for the project and program management organization, ensuring strong alignment between business strategy and technology delivery. This role is responsible for building a high-performing team of project / program managers and business analysts that are accountable for executing our Technology Roadmap. Our teams operate using a hybrid approach of agile methodologies and are expected to continuously be retrospective with our project execution approach to continually improve. As the primary steward of delivery excellence, this leader ensures that initiatives are well-defined, well-planned, well-resourced, and well-executed, from initial concept through postlaunch optimization. The VP partners closely with business sponsors, engineering, operations, marketing, and external partners to help build our Technology roadmap and deliver measurable outcomes with transparency, predictability, and quality.

Requirements

• 15+ years of technology program/project leadership; 8+ years leading senior PMO or program teams in complex environments.
• Proven success delivering large-scale, multi-year technology initiatives.
• Strong experience with portfolio management, direct budget oversight, resource planning, and executive-level reporting.
• Expertise in SDLC, agile/hybrid methodologies, and cross-functional delivery.
• Demonstrated ability to lead through influence, communicate crisply, and manage senior stakeholders.
• Strategic, structured, and highly organized: can translate strategy into an executable plan, then manage trade-offs
• A strong communicator with executive presence.
• An expert builder of teams, processes, and operational discipline: can operate as a leader of leaders and coach senior PMs
• Comfortable in fast-moving, evolving environments.
• Driven by accountability, clarity, and delivering results.
• Executive-level communication and the ability to influence at all levels
• Expertise in portfolio management and strategic prioritization
• Proven ability to manage an organization to a high level of performance
• Strong command of SDLC, agile delivery, and cross functional collaboration
• Ability to scale processes and elevate organizational delivery maturity
• Strong judgment, decision-making, and critical thinking skills
• Demonstrated success in leading change across complex environments

Nice To Haves

• Experience building or scaling PMOs is highly preferred.
• Certifications such as PMP, PgMP, SAFe, or Prosci are a plus.

Responsibilities

• Strategic Alignment & Portfolio Leadership Ensure all programs and projects align with strategic business goals, including revenue growth, conversion optimization, customer experience, operational efficiency, and scalability.
• Translate high-level business objectives into actionable delivery frameworks and structured execution plans.
• Partner with executives to define business outcomes, success metrics, and prioritization across the portfolio.
• Drive alignment between Engineering and Business stakeholders on investment decisions and dependencies.
• Develop and maintain the overall Technology Roadmap, ensuring the organization has clarity on what the Technology organization is committed to delivering and by when.
• Scope & Requirements Governance Ensure each initiative has a clear and shared definition of scope, business intent, and definition of done.
• Oversee the development of functional and non‑functional requirements, ensuring consistency and alignment across teams.
• Establish governance practices that prevent scope creep and ensure disciplined change control.
• Planning, Scheduling & Delivery Execution Lead the creation and review of good/better/best staffing and delivery models for initiatives.
• Establish project delivery frameworks, milestone structures, and enterprise-wide planning standards.
• Ensure predictable delivery through realistic schedules, cross-team dependency mapping, and proactive mitigation of blockers.
• Facilitate cross-functional alignment for date-driven initiatives versus scope-driven initiatives.
• Budget, Resource & Capacity Management Drive disciplined resource allocation across a complex, multi-team organization with competing priorities, aligning capacity to the highest-priority initiatives and business outcomes.
• Oversee resource planning across Engineering, QA, UX, Data, Infrastructure, and other functional teams.
• Partner with Finance and Technology leadership to actively manage budgets and track actuals vs. plan, optimizing resource utilization and investment outcomes across internal teams, external partners, vendors, tools, and contracts.
• Optimize resource allocation based on strategic priorities, capacity constraints, and portfolio-level trade-offs.
• Enterprise Risk Management Identify and classify risks related to complexity of change, business readiness, resourcing, security, scalability, or process gaps.
• Lead a structured risk management discipline including tracking, mitigation planning, and executive escalation.
• Establish standards for risk scoring, communication, and accountability across all programs.
• Executive & Stakeholder Communication Act as the primary communication bridge across business, technology, operations, and executive leadership.
• Deliver transparent, concise reporting on program health, risks, schedule adherence, scope changes, and financial impacts.
• Ensure consistent communication practices across the Project Delivery org to improve predictability, visibility, and trust.
• Vendor & Third-party Management Oversee relationships with contract resource providers and third-party vendors in partnership with Technology leadership.
• Ensure external partners meet delivery expectations, technical requirements, and contractual obligations.
• Improve operating models for blended teams and outsourced resources.
• Postlaunch Monitoring & Continuous Improvement Lead the operational readiness and go live planning processes for major initiatives.
• Monitor post‑launch KPIs (e.g., conversion, uptime, performance) and drive closure of issues required to meet definition of done.
• Drive continuous improvement in delivery practices, cross-team collaboration, and operational maturity.
• Governance, Standards & Documentation Own and maintain the enterprise Technology Roadmap and communicate key changes to the organization.
• Ensure the roadmap accurately reflects Technology’s committed work and readiness to take on new initiatives.
• Establish and enforce PMO standards, SDLC best practices, documentation rigor, audit trails, decision logs, and compliance processes.
• Drive organizational maturity in program governance, execution transparency, and delivery accountability.

Benefits

• Health & wellness: Comprehensive and heavily subsidized medical, dental, and vision plans, plus on-site gym access, holistic wellness sessions, and group fitness classes
• Time for you: Substantial Paid Time Off (PTO), and 11 paid holidays- including Juneteenth, Memorial Day, Labor Day – and Summer Fridays. Plus- extensive parental leave, with up to 12-16 weeks paid leave at 100% base salary.
• Travel more, spend less: 50% off our trips for you and a companion, 25% for additional immediate family members, and exclusive quarterly associate travel deals
• Your future, secured: 401(k) with company match, life insurance, and disability coverage
• Continuous growth: Tuition assistance for both professional and personal development, opportunities for professional development through oversees travel, and direct access to Pinnacle Leadership & Team Development.
• Extra perks: Commuter benefits, FSA options, pet insurance, home & auto discounts, and paid volunteer time off to give back to the community

What This Job Offers

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