Senior Program Manager

About This Job

We are seeking a Senior Program Manager who operates as an AI-native leader — someone who has fundamentally rewired how they plan, communicate, and deliver complex multi-team programs around AI-assisted workflows. In this role, you will own the orchestration of large, cross-functional programs that span multiple engineering teams, product lines, and business stakeholders, driving strategic outcomes through structured governance, executive communication, and disciplined dependency management. You will partner with product owners, engineering leadership, and business stakeholders to translate strategic priorities into coordinated delivery plans, leverage AI copilots and analytics platforms to provide real-time program health and forecasting, and model what it looks like to lead programs in an AI-augmented environment. Your ability to lead through influence, navigate ambiguity, and elevate the quality of executive-level communication will be central to your success.

Department: Product Development Reports to: EVP Software Engineering Direct Reports: None

Essential Responsibilities

• Lead end-to-end orchestration of strategic, multi-team programs from initiation through closure — program charters, governance models, milestone planning, stakeholder maps — using AI-assisted analysis to surface dependencies, estimate effort, and identify blind spots early.
• Partner with product owners, engineering leadership, and business stakeholders to align on objectives, success criteria, and prioritization. Drive coordinated delivery plans across workstreams without owning the individual project execution.
• Manage program-level dependencies, risks, and trade-offs across teams. Use AI-powered analytics and predictive models to provide real-time program health, early warning on slippage, and data-driven trade-off recommendations to executive sponsors.
• Facilitate steering committee meetings, stage-gate reviews, and executive briefings. Use AI summarization and synthesis tools to distill complex multi-workstream status into clear, audience-appropriate narratives.
• Prepare and deliver program status reports, portfolio dashboards, and executive briefings by automating routine reporting through AI-generated summaries, trend analysis, and visualization — reserving your time for narrative insight and strategic commentary.
• Identify program-level issues and risks using both human judgment and AI-assisted pattern recognition. Lead development of mitigation plans and manage escalations with supporting evidence from automated analytics.
• Maintain RAID logs, decision logs, and program documentation as living artifacts. Use AI tools to keep documentation current and accelerate the production of governance materials.
• Drive cross-team retrospectives and continuous improvement at the program level, using AI tools to identify recurring blockers and recommend process adjustments backed by historical program data.
• Evaluate, pilot, and operationalize new AI tools and workflows for the program management function. Serve as an SME on AI-assisted program delivery and establish standards for when and how AI tooling should be applied.
• Mentor and coach Project Managers and Technical Project Managers on effective AI adoption — moving from manual workflows to AI-augmented processes while maintaining critical thinking, accountability, and human oversight.
• Build strong relationships with Product Development, IT, Operations, and key business stakeholders. Use AI-powered meeting preparation (agenda generation, pre-read summarization, action-item tracking) to make every interaction more productive.
• Develop and maintain program risk and governance frameworks that incorporate AI-driven risk scoring, automated monitoring, and early-warning triggers alongside traditional qualitative assessment.
• Collaborate with global stakeholders during overlapping onsite hours. Champion asynchronous, AI-enhanced communication practices (automated stand-up summaries, intelligent thread digests) to bridge time zone and schedule gaps.
• Promote AI-augmented best practices across the program management discipline — contributing to internal playbooks, training sessions, and communities of practice.

Knowledge, Skills, and Abilities

• Strong understanding of the SDLC — Waterfall, Iterative, and modern CI/CD-driven delivery models — and the ability to operate fluently alongside engineering teams without driving technical implementation decisions.
• Proficiency with program and portfolio management platforms (Azure DevOps, Jira, MS Project, or equivalent), with the ability to leverage integrations, automations, and intelligent dashboards for program reporting.
• Familiarity with Scrum, Kanban, Waterfall, and Scaled Agile Framework (SAFe).
• Ability to critically evaluate AI-generated outputs — knowing when AI accelerates work, when it introduces risk, and how to maintain human oversight and accountability.
• Demonstrated success delivering complex, multi-team programs from inception to delivery in fast-moving environments.
• Experience operating at the intersection of business and technology, with a track record of earning trust across executive, technical, and non-technical audiences.
• Ability to make data-driven decisions and recommendations using evidence and pragmatic judgment.
• Strong relationship-building skills, with the emotional intelligence to lead change management around new ways of working.
• Excellent oral and written communication, including the ability to present to executive audiences and tailor communications to different stakeholders.
• Strong influence and negotiation skills to drive programs forward, clear roadblocks, and resolve conflicts without direct authority.

AI Tooling Expectations

The ideal candidate is already using AI tools daily in their program management work. This means hands-on experience with AI copilots (Claude, ChatGPT, Copilot, or equivalent), automated recurring tasks like meeting summarization, status reporting, and portfolio analysis, and the ability to configure AI-enhanced workflows within tools like Azure DevOps, Jira, Slack, or Teams. You should be comfortable evaluating new AI tools and making build-vs-buy-vs-prompt recommendations for the PM function. We are not looking for someone who needs to be convinced that AI is useful — we are looking for someone who has already proven it in their work.

Working Conditions

• No direct reports; this role provides mentorship, coaching, and AI workflow guidance to Project Managers, Technical Project Managers, and cross-functional team members.
• General indoor office environment or working from home.
• Sedentary work; sitting most of the time, with occasional walking and standing.

• 10+ years of professional experience leading complex programs within cross-functional environments, with at least 2 years actively integrating AI tools into program management workflows.
• Demonstrated track record of orchestrating multi-team, multi-quarter programs to successful business outcomes.
• Bachelor's degree in Business, IT, Computer Science, or a related field. Master's degree preferred.
• PMP, PRINCE2, PgMP, or SAFe certifications preferred.
• Demonstrated experience using AI copilots, LLM-based tools, or automation platforms (e.g., GitHub Copilot, Claude, ChatGPT, Cursor, or equivalent) in a professional program delivery context.

Welcome to arrivia. We specialize in making brands better through the power of travel. With more than 55 years of combined experience, we're a merger of three powerhouse brands — ICE, SOR Technology, and WMPH Vacations — combining decades of travel industry leadership. With offices on both coasts of the US and around the world, we embrace diversity and a passion for travel across our global staff. We're focused on building a customer-first culture, fueled by the best travel experiences for all our members at every point in their journey. Our Core Values

• Stay Curious – Explore new challenges and make space to learn, grow and improve
• Keep it Real – Earn trust through open, honest, and clear communication
• Own it – Seek ways to make an impact and take action
• Win Together – Create a culture of connection and inclusion where everyone can be their best We believe in bringing your whole self to work every single day and consider every applicant on an equal opportunity basis.