Senior Project Manager – Digital Transformation (Remote)

Job Title: Senior Project Manager – Digital Transformation (Remote)
Location: Remote (Costa Rica or Mexico)
Job Summary
We are seeking an experienced Senior Project Manager to lead the successful planning, execution, and delivery of complex digital transformation initiatives. The ideal candidate will have extensive experience managing cross-functional teams, driving Agile project execution, and delivering high-impact digital solutions. This role requires strong leadership, exceptional stakeholder management skills, and the ability to leverage modern AI tools to enhance project delivery and knowledge management.
Key Responsibilities

• Lead end-to-end delivery of complex digital projects from initiation through implementation and post-launch support.
• Manage multiple concurrent projects while ensuring delivery within scope, schedule, budget, and quality expectations.
• Collaborate with cross-functional teams including business stakeholders, engineering, architecture, QA, release management, and product teams.
• Drive project execution using Agile and Waterfall methodologies based on business needs.
• Facilitate sprint planning, backlog grooming, daily stand-ups, retrospectives, and project status meetings.
• Develop and maintain project plans, risk registers, issue logs, and executive-level reporting.
• Utilize Atlassian tools such as Jira and Confluence for project tracking, documentation, and reporting.
• Build and enhance project knowledge repositories and improve team collaboration.
• Leverage AI agents and Large Language Models (LLMs) to improve project management workflows, documentation, reporting, and operational efficiency.
• Monitor project performance using KPIs and metrics, identifying opportunities for continuous improvement.
• Manage project budgets, resource allocation, forecasting, and financial reporting.
• Communicate project status, risks, dependencies, and mitigation strategies to stakeholders and leadership.

Required Qualifications

• Bachelor's degree in Business, Information Technology, Computer Science, Engineering, or a related field.
• 10+ years of project management experience with a strong focus on digital project execution.
• Proven experience delivering digital initiatives such as:
  • Omnichannel (OMNI) solutions
  • Loyalty platforms
  • Marketplace implementations
  • Front-end/web application projects
• Strong experience with Agile and Waterfall project management methodologies.
• Hands-on experience using Jira for project execution and Confluence for documentation and reporting.
• Experience building, implementing, or leveraging AI agents to improve business or project operations.
• Practical experience working with Large Language Models (LLMs) such as ChatGPT, Claude, Microsoft Copilot, or similar AI platforms.
• Demonstrated success delivering projects from initiation through production deployment.
• Strong analytical, organizational, and problem-solving skills.
• Excellent communication, presentation, and stakeholder management abilities.
• Experience leading geographically distributed and cross-functional teams.
• Proven experience managing project budgets, timelines, risks, and vendor coordination.
• Strong understanding of SDLC and software development best practices.

Preferred Qualifications

• Project Management Professional (PMP) certification.
• Certified ScrumMaster (CSM) or equivalent Agile certification.
• Experience working in enterprise-scale digital transformation environments.
• Familiarity with AI-driven productivity and automation tools.

Key Skills

• Project Management
• Digital Transformation
• Agile & Scrum
• Waterfall Methodology
• Jira
• Confluence
• AI Agents
• Large Language Models (LLMs)
• ChatGPT
• Claude
• Microsoft Copilot
• Budget Management
• Risk Management
• Stakeholder Management
• Resource Planning
• Sprint Planning
• Cross-functional Team Leadership
• KPI & Metrics Management
• SDLC
• Executive Reporting

What We're Looking For
The ideal candidate is a strategic and execution-focused project management leader who thrives in fast-paced environments. They possess a strong background in digital program delivery, embrace AI-enabled ways of working, and excel at leading diverse teams to deliver successful business outcomes while maintaining high standards of quality, collaboration, and operational excellence.