
Roberto Castillejo
Verified Expert in Project Management
Project Manager
Lima, Peru
Toptal member since September 8, 2026
Roberto is a project manager with 16+ years of experience leading global, remote, hybrid, and on-site teams. He has a background in military, aerospace, and education, with strong expertise in project delivery and team leadership. Roberto is experienced with Asana, ClickUp, Claude, and AI-powered tools.
Project Highlights
Expertise
- AI Project Management
- Asana
- ClickUp
- Cross-cultural Management
- Digital Project Management
- Operations Management
- Program Management
- Team Leadership
Work Experience
Head of PMO & PM Lecturer
Institute of Project Management
- Strengthened PMO and staff governance by overseeing team performance, compliance, portfolio coordination, and strategic projects across the organization.
- Optimized the organizational structure, processes, procedures, autiomations, and operational standards to improve efficiency, accountability, and consistency across a global team.
- Delivered project management lectures to learners across Europe and the UK, supporting the development of practical project management capabilities in an international remote learning environment.
Air Force Officer
Peruvian Air Force
- Managed over 90 team members and high-value assets (exceeding $100 million) across more than 10,000 hours of air logistics operations.
- Collaborated with commercial, compliance, complaint management, and public relations teams, consistently achieving over 90% of objectives on time and within budget.
- Planned and oversaw the efficient and timely execution of more than USD 3.2 million in expenditures in accordance with national regulations, including the strategic reallocation of additional funds when necessary.
Project History
Field Training Excercise
- 299 Sorties — of Total Number of Flight Missions Successfully Synchronized Across Partner Forces
- 194,200 Tons — of Total Weight of Equipment, Operational Supplies, & Sustainment Materials Transported
The need to improve the readiness of US and partner nation militaries through humanitarian assistance and disaster response, space domain awareness, cybersecurity, special operations and counter-threat exercises, legal and medical exchanges, and construction projects.
Once the challenge was clearly defined, I led the planning process from the Air Logistics Operations Peruvian team. The proposed solution focused on identifying each team’s capabilities and resources and aligning them with the exercise requirements. I coordinated with multinational and multi-agency stakeholders to define responsibilities, timelines, locations, reporting, and escalation procedures. Once agreed, the plan was formally approved and executed, requiring extensive coordination and multiple levels of authorization.
I integrated 1,500+ personnel across 7 nations, delivering care to 1,200+ patients, 80 surgeries, 2,380 supply boxes, 299 air sorties, 1,200+ ground movements, and 194,200+ tons of cargo, strengthening regional interoperability.
Production Operating System
- 6 Months — Production Forecast Scope Achieved
- 98% — Schedule Adherence Achieved
The pipeline had been built for a smaller operation. To plan 6 months ahead across dozens of concurrent projects composed mainly of videos and animations, we needed a single planning layer that could show capacity, sequence work, reduce idle time, and route reviews—without adding coordination overhead to a team already working at pace.
I built a Planning Matrix with lanes by person and by program, giving a live view of who holds what, in what status, and where capacity opens up. More than 30 native automations route each deliverable to the right approver, timestamp submissions against due dates, and feed a performance database supporting two team KPIs: Schedule Adherence and First Pass Acceptance.
Production is now planned 6 months out, with capacity gaps identified before they lead to idle time. Reviews route without chasing, and every deliverable feeds a dataset that sharpens future estimates.
Remote Operations Architecture Optimization
- 100% — Processes Documented
- 90% — Task Visibility Rate
The organization’s global team grew rapidly, and the existing management platform was no longer sufficient to manage teams efficiently. This made it challenging to maintain proper visibility and track ongoing activities, including routine tasks and projects.
The first step was to identify and break down each team member’s processes and activities to a level sufficient for management and planning. The structure was then defined by assigning responsibilities, estimated times, native automations, access requirements, and task locations. Once identified, it was created on the collaborative platform, and teams were progressively onboarded, with the most critical teams added last. Finally, cultural management was implemented to support the adoption of the new way of working.
The solution provided greater visibility and control over daily activities and projects across departments, improving the structure ready to start with external automations and AI features.
Education
Specialization in Artificial Intelligence
ESAN Graduate School of Business - Lima, Peru
Master's Degree in Project Management
Peruvian Technological University - Lima, Perú
Master's Degree in Public Administration
San Martin de Porres University - Lima, Perú
Bachelor's Degree in Airspace Management
Peruvian Air Force - Lima, Peru
Certifications
PMO Certified Professional (PMI-PMOCP)
Project Management Institute (PMI)
Project Management Professional (PMP)
Project Management Institute (PMI)
Skills
Tools
Claude, Asana
Paradigms
Change Management, AI Project Management
Other
Operations Management, Schedule Management, Scope Management, People Management, Team Leadership, Strategy, Stakeholder Management, Public Policy, Digital Project Management, Cross-cultural Management, Program Management, Portfolio Management, PMO, ClickUp, Risk Management, Project Management, Budget Planning, Artificial Intelligence (AI), Large Language Models (LLMs), Responsible AI, Technical Program Management
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