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
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-facing project management role overseeing technical projects with 5+ team members and $1M+ budgets
- Experience overseeing multi-faceted P&L for portfolios of $15M+ in value with proven forecasting and budgeting skills
- Deep expertise in project delivery across cloud modernization, application development, or data engineering
- Extensive knowledge of project methodologies and tools, with certifications (PMP, CSM, PSM)
- Strong executive presence and communication skills, capable of performance coaching, strategic conversations, and executive communication at any organizational level
- Skilled in building and scaling delivery standards, processes, and governance frameworks
Preferred Qualifications
- Proven track record in employee engagement, performance management, and talent development across multiple teams
- Familiarity with HR processes and organizational development practices
- Experience delivering projects on AWS or other major cloud providers
- Background in Professional Services operations including utilization management, capacity planning, and resource optimization
- Experience with SOW review and contract risk assessment
- Track record of supporting sales processes and account growth through delivery excellence
- 100% remote work
- Equitable Life - Hybrid Plan
- 100% Premium Coverage for the employee and dependents
- 4% Pension match (employer contribution)
- Unlimited Vacations
- Sick Leave
- Paid Holidays
- Parental Leave
- Competitive stock options plan
- Paid for exams and certifications
- Peer bonus awards
- State of the art laptop and tools
- Equipment & Office Stipend
- Individual professional development plan
- Annual stipend for Learning and Development
- Work with an amazing worldwide team and in an incredible corporate culture
This role may require up to 25% travel, depending on business needs.
Base Salary Range: The expected base salary range for this position is CAD 220,400 - CAD 246,500 per year, commensurate with experience and qualifications.
Additional Compensation Components: In addition to the base salary, the compensation package may include bonuses, commissions, equity, and other incentives. The specific components will vary depending on the role and individual and/or company performance.
NOTE: We’re unable to provide visa sponsorship now or at any time in the future.
At Caylent, we are committed to fair, transparent, and inclusive hiring practices. As part of our recruitment process, we may use artificial intelligence (AI) tools or automated systems to assist with the screening and evaluation of applications to help match candidate qualifications with job requirements.
These tools are designed to support — not replace — human decision-making. Final hiring decisions are always made by our trained recruitment professionals.
If an AI or automated tool is used during your application process, it will only be in accordance with applicable laws and regulations, and your information will be handled in a secure and confidential manner.
If you have any questions, please contact [email protected]
Caylent is a place where everyone belongs. We celebrate diversity and are committed to creating an inclusive environment for all employees. Our approach helps us to build a winning team that represents a variety of backgrounds, perspectives, and abilities. So, regardless of how your diversity expresses itself, you can find a home here at Caylent.
We are proud to be an equal opportunity employer. We prohibit discrimination and harassment of any kind based on race, color, religion, national origin, sex (including pregnancy), sexual orientation, gender identity, gender expression, age, veteran status, genetic information, disability, or other applicable legally protected characteristics. If you would like to request an accommodation due to a disability, please contact us at [email protected].
