Senior Delivery Leader - Cloud & Transformation Programs

Ensono; Chicago (IL); Remote; USD 155,000 - 210,000; Full time

Benefits offered by this job

Unlimited Paid Days Off

Health plan options

401k with company match

Dental, vision, disability, life & FSA

Education Reimbursement

Sabbatical leave

Wellness program

Flexible work schedule

Job summary

Ensono is seeking a Principal Project Manager (Consultant) to lead complex programs across the full software development lifecycle for US-based clients. You will influence senior stakeholders, shape program vision, and drive delivery excellence while mentoring teams and advancing delivery capabilities.

This role emphasizes cloud transformation, governance, and strategic business outcomes. You will manage budgets, risks, and cross-functional teams, delivering measurable value and maintaining

Qualifications

• Bachelor’s degree in Business, Information Technology, Computer Science, Engineering, or related discipline, or equivalent experience.
• 10+ years of experience leading enterprise technology delivery programs or digital transformation engagements.
• Experience delivering cloud transformation, application modernization, microservices and enterprise platform initiatives.
• Strong understanding of SDLC, DevOps, CI/CD pipelines, and release management.
• Proficiency with Agile and traditional delivery frameworks; know when to apply each.
• Advanced proficiency with Azure DevOps and Atlassian products; Smartsheet desired.

Responsibilities

• Lead complex programs and interconnected workstreams with clear outcomes and milestones.
• Define and evolve delivery methodologies, planning standards, and tools.
• Translate strategic goals into executable delivery roadmaps and governance.
• Influence senior stakeholders and steering committees on vision and investments.
• Develop long-term client engagement strategies leveraging delivery experience and emerging technologies.
• Act as a trusted adviser balancing client strategy, delivery feasibility, and commercial goals.

Skills

Leadership

Budget management

SDLC

Agile

Cloud transformation

Executive communication

Education

Bachelor’s degree or equivalent

Tools

Azure DevOps

Atlassian tools

Smartsheet

Job description

Ensono is seeking a Principal Project Manager (Consultant) to lead complex programs across the full software development lifecycle for US-based clients. You will influence senior stakeholders, shape program vision, and drive delivery excellence while mentoring teams and advancing delivery capabilities.

This role emphasizes cloud transformation, governance, and strategic business outcomes. You will manage budgets, risks, and cross-functional teams, delivering measurable value and maintaining