Principal CXS Strategic Programs

This is a fully remote position, open to applicants in Costa Rica.

📋 Description

• Lead and manage cross-functional strategic programs related to CXS transformation, AI-driven workflow enhancements, evolution of operating models, integration planning, and initiatives sponsored by the CCO.

• Convert executive priorities into program charters, workstreams, milestones, responsible parties, decision-making paths, dependencies, and quantifiable outcomes.

• Collaborate with CXS leaders and departments such as Operations, Finance, HR, Internal Communications, IT, Data, AI, Legal, and other stakeholders.

• Identify and redesign tasks for simplification, automation, AI enhancement, or improved operational practices.

• Progress transformation opportunities from evaluation to pilot, adoption, and scaling.

• Establish KPIs, baselines, reporting schedules, dashboards, and follow-up systems.

• Prepare materials for decision-making, executive updates, operational briefs, and recommendations.

• Create visibility at the portfolio level for CCO-sponsored initiatives, highlighting progress, risks, tradeoffs, decisions, and organizational impacts.

• Develop reusable tools, playbooks, lessons learned, case studies, and shared operational frameworks.

• Gather senior CX Operations Principals through shared context, operational rhythms, common tools, and coordinated workback strategies.

• Leverage AI/ML project experience to define use cases, coordinate data and technology dependencies, manage pilots, and guide solutions from adoption to scaling.

• Report to the Chief of Staff to the CCO and function as a principal-level individual contributor without direct reports.

⛳️ Requirements

• Extensive experience in leading intricate, cross-functional programs within a SaaS, technology, professional services, public-sector technology, management consulting, strategic operations, or a similarly complex environment.

• Preferred experience in business transformation, operating model changes, acquisition or integration planning, executive operations, or strategic initiatives.

• Proven ability to create and implement KPIs, reporting systems, program governance, or operational rhythms that link activities to measurable results.

• Experience working with senior leaders and cross-functional teams on sensitive, high-priority, or ambiguous projects.

• Relevant experience in consulting, operations, transformation, or strategy is preferred.

• Demonstrated experience in contributing to or leading AI/ML projects from discovery and business case development through pilot, implementation, adoption, and tracking measurable outcomes.

• Strong capabilities in strategic operations, transformation, program leadership, and stakeholder management in matrixed settings.

• Knowledge of AI-enabled process redesign, automation, productivity enhancement, technology adoption, or operational transformation.

• Familiarity with AI/ML project lifecycles, including use-case definition, data preparedness, model or solution evaluation, responsible AI considerations, implementation, adoption, and value measurement.

• Strong analytical judgment, including KPI design, performance monitoring, value tracking, assumptions, and synthesis suited for executive-level presentation.

• Exceptional written and verbal communication skills.

• High discretion and sound judgment in workforce planning, organizational transitions, financial information, or sensitive change management work.

• Ability to structure ambiguous priorities, clarify ownership, frame decisions, and drive initiatives through influence rather than authority.

• Ability to foster a shared context, establish operational cadence, and cultivate followership among senior peers and cross-functional collaborators.

🏝️ Benefits

• Flexible Time Off

• Company-Wide Wellbeing Days (paid days off)

• Work From Home Reimbursement

• Private health, vision, dental, and life insurance for employees and their families

• On-Demand Mental Health Support, including access to Headspace and other wellness tools

• Paid Parental Leave for both birthing and non-birthing parents

• Online Learning Platforms for professional development

• Competitive Salary & Bonuses

• Remote-first work environment