Senior Manager of Project Management

Summary

Join Caylent as a Sr. Manager of Project Management to lead and scale multiple teams of Project Managers. You will oversee a significant portfolio of projects, manage P&L, and ensure successful execution. Responsibilities include team leadership, talent management, portfolio operations, delivery excellence, and governance. The ideal candidate has 10+ years managing project manager teams, 15+ years in a client-facing project management role, and deep expertise in cloud project delivery. Caylent offers a competitive compensation package, including benefits like medical, dental, vision, 401k, and unlimited PTO.

Requirements

• 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
• 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
• 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
• 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

Responsibilities

• 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
• 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
• 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

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

Benefits

• Medical Insurance for you and eligible dependents
• 401k plan with company match up to 4% and immediate vesting
• Competitive phantom equity
• Company issued laptop
• Dental and Vision insurance
• Term Disability Insurance
• Term Life Insurance
• Flexible Spending Account
• Equipment & Office Stipend
• Annual stipend for Learning and Development
• Unlimited Paid Time Off
• 10 Paid Holidays