Senior Manager of Project Management

Caylent is a cloud native services company that helps organizations bring the best out of their people and technology using Amazon Web Services (AWS). We provide a full-range of AWS services including workload migrations and modernization, cloud native application development, DevOps, data engineering, security and compliance, and everything in between.

At Caylent, our people always come first.  We are a global company and operate fully remote with employees in Canada, the United States, and Latin America. We celebrate the culture of each of our team members and foster a community of technological curiosity. Come talk to us to learn more about what it means to be a Caylien!

The Mission

We are seeking an exceptional Sr. Manager of Project Management to join our growing Cloud Project Management team as a PM Portfolio Leader. The right candidate is an experienced senior leader who brings expert-level delivery and project governance skills, significant business acumen, and a passion for scaling high-performing teams. Your mission is to lead, coach, and scale multiple teams of Project Managers across a significant ($15M+) book of business, ensuring successful execution across cloud delivery engagements while driving operational excellence, customer success, and business growth.

Your Assignment

Team Leadership & Talent Management

• Lead and support multiple teams of Project Managers across a significant portfolio
• Own hiring, onboarding, and professional development for direct reports and extended teams
• Conduct regular 1:1s, performance check-ins, and interviews at various organizational levels
• Demonstrate proven performance management experience including up-leveling, training, and tactful performance management

Portfolio & Business Operations

• Oversee multi-faceted P&L for a significant ($15M+) portfolio of accounts and projects
• Manage Professional Services operations including utilization, capacity planning, and revenue targets
• Navigate complex customer escalations and negotiations while balancing Caylent's financial interests with customer and AWS needs
• Review contractual documents (SOWs) to identify and mitigate risk while supporting sales processes
• Work collaboratively with sales teams to resolve issues, progress deals, and grow accounts through excellent delivery

Delivery Excellence & Governance

• Ensure proper PM governance is established and executed across all portfolio engagements
• Monitor key project health indicators and collaborate with Portfolio PM leaders to enhance reporting and governance mechanisms
• Work closely with Portfolio CTOs and Engagement Leads to ensure alignment between PM practices and portfolio needs
• Represent CPM to provide delivery SOW approvals and support pre-sales processes where PM approach is key
• Provide direct project support periodically as a Sr. PM/Engagement to cover gaps and stay connected to delivery challenges

Your Qualifications

Core Consulting Qualifications

Customer Experience

• Leads planning sessions to align leadership on strategic goals and transformation strategies
• Creates comprehensive roadmaps that connect business value to organizational goals, ensuring buy-in and measurable outcomes
• Demonstrates ability to navigate complex customer escalations while balancing multiple stakeholder interests
• Demonstrated experience leading a team of project managers in the successful delivery of complex, large-scale cloud projects on the AWS platform. Responsibilities include resource planning, risk management specific to cloud environments, and stakeholder communication across technical and non-technical audiences, ensuring projects are delivered on time and within budget.

Collaboration

• Coaches teams through change by addressing resistance effectively and aligning cross-functional teams
• Drives growth for Caylent by identifying needs and mapping capabilities to long-term business strategies
• Works collaboratively across Portfolio CTOs, sales teams, and technical teams while managing constantly shifting priorities

Communication

• Provides executive level recommendations that align technical delivery with business vision
• Acts as a consulting SME for teams and clients, guiding strategic conversations and value-driven decision making

Technical Qualifications

• 10+ years of experience managing teams of project managers or delivery consultants, with demonstrated experience managing medium to large teams
• 15+ years in a client-f