Delivery Director, Application Modernization

Intuitive.ai; United States; Remote; CAD 250,000 - 388,000; Full time

Job summary

Intuitive.AI is seeking a Delivery Director, Application Modernization to lead enterprise-scale modernization programs across client portfolios, spanning .NET/Java, cloud transformation, and platform modernization.

You will own end-to-end delivery, governance, budgets, and stakeholder satisfaction, partnering with Practice Leaders, Solution Architects, and executives to drive outcomes in regulated industries. The role is remote across USA/Canada with a focus on delivery excellence and growth.

Qualifications

• 15+ years of experience in software engineering, enterprise technology, or digital transformation.
• Minimum 8+ years leading enterprise-scale delivery programs.
• Proven experience delivering large Application Modernization and Cloud Transformation initiatives.
• Strong understanding of modernization approaches including: Rehost (Lift & Shift), Replatform, Refactor, Rearchitect, Rebuild, Replace
• Experience with .NET and/or Java modernization programs.
• Experience managing multi-vendor, distributed, and global delivery teams.
• Demonstrated success managing executive stakeholders and steering committees.
• Strong experience in program governance, portfolio management, and delivery operations.
• Experience with Agile, SAFe, Hybrid, and Traditional delivery methodologies.
• Experience delivering within Banking, Financial Services, Insurance, Healthcare or other regulated industries.
• Strong understanding of DevSecOps, CI/CD, Cloud Engineering, and Platform Modernization.

Responsibilities

• Own end-to-end delivery of large-scale Application Modernization programs from assessment through modernization and production rollout.
• Lead multiple concurrent modernization engagements with accountability for scope, schedule, quality, financial performance, and customer satisfaction.
• Establish delivery governance frameworks, reporting structures, risk management processes, and escalation mechanisms.
• Drive execution across modernization initiatives including rehosting, replatforming, refactoring, re-architecting, cloud migration, and cloud-native transformation.
• Ensure successful implementation of modernization roadmaps while minimizing business disruption and operational risk.
• Act as the executive point of contact for client delivery leadership.
• Build trusted relationships with CIOs, CTOs, Enterprise Architects, and Business Leaders.
• Conduct steering committee reviews, executive status reporting, risk reviews, and program governance meetings.
• Align modernization initiatives with business objectives, transformation goals, and expected outcomes.
• Manage customer expectations and ensure successful delivery outcomes.
• Manage multi-million-dollar modernization portfolios and delivery budgets.
• Own resource forecasting, utilization management, margins, revenue realization, and financial performance.
• Review project health, staffing models, delivery KPIs, and operational metrics.
• Work with Practice and Sales leaders to support account growth and expansion opportunities.
• Provide oversight of Statements of Work (SOWs), change requests, commercial governance, and contract compliance.

Skills

Delivery leadership

Program management

Stakeholder management

Enterprise delivery

Cloud transformation

Agile methodologies

DevSecOps

Leadership development

Cross-functional collaboration

Strategic thinking

Education

Bachelor's degree in Computer Science or related

Master's degree preferred

Tools

AWS

OpenShift

Terraform

CI/CD

Job description

Intuitive.AI is one of the fastest-growing (INC 5000, CRN) Cloud & SDx solution and services companies supporting enterprise customers on a global scale. Intuitive is an "Engineering Company" delivering measurable value and key business outcomes.

Intuitive Superpowers:

- DataOps & AI/ML

- Cybersecurity (App/Data/Infra) & GRC

- SDx & Digital Workspace

We are proud to partner with some of the world's leading enterprises and serve 200+ customers across different industry verticals. We have achieved many milestones along the way, including being recognized as a top-10 fast-growth 150 IT company in the Americas by CRN in 2022 and being named one of America's fastest-growing private companies by INC 5000 in 2022. That’s not all! Even CIO Review awarded us as the Most Promising Cloud Migration Company and Artificial Intelligence Solutions Provider in 2022.

About the job:

Title: Delivery Director, Application Modernization

Location: Remote across USA/ Canada

Position Type: Full Time

About the Role

We are seeking an experienced Delivery Director, Application Modernization, to lead and govern enterprise-scale modernization programs across our clients. This strategic leadership role is responsible for end-to-end delivery ownership, client success, program governance, financial management, and execution excellence for complex application transformation initiatives.

The ideal candidate will bring deep experience leading large modernization engagements involving legacy .NET and/or Java applications, cloud transformation, platform modernization, and digital transformation programs. This individual will oversee multiple modernization portfolios, manage senior client stakeholders, drive operational excellence, and ensure successful outcomes across regulated industries such as Financial Services, Banking, Insurance, Healthcare, and Manufacturing.

The Delivery Director will partner closely with Practice Leaders, Solution Architects, Engineering Leaders, Sales, and Executive stakeholders to ensure predictable delivery, customer satisfaction, and business growth.

Key Responsibilities

Delivery & Program Leadership

• Own end-to-end delivery of large-scale Application Modernization programs from assessment through modernization and production rollout.
• Lead multiple concurrent modernization engagements with accountability for scope, schedule, quality, financial performance, and customer satisfaction.
• Establish delivery governance frameworks, reporting structures, risk management processes, and escalation mechanisms.
• Drive execution across modernization initiatives including rehosting, replatforming, refactoring, re-architecting, cloud migration, and cloud-native transformation.
• Ensure successful implementation of modernization roadmaps while minimizing business disruption and operational risk.

Client & Executive Stakeholder Management

• Act as the executive point of contact for client delivery leadership.
• Build trusted relationships with CIOs, CTOs, Enterprise Architects, and Business Leaders.
• Conduct steering committee reviews, executive status reporting, risk reviews, and program governance meetings.
• Align modernization initiatives with business objectives, transformation goals, and expected outcomes.
• Manage customer expectations and ensure successful delivery outcomes.
• Manage multi-million-dollar modernization portfolios and delivery budgets.
• Own resource forecasting, utilization management, margins, revenue realization, and financial performance.
• Review project health, staffing models, delivery KPIs, and operational metrics.
• Work with Practice and Sales leaders to support account growth and expansion opportunities.
• Provide oversight of Statements of Work (SOWs), change requests, commercial governance, and contract compliance.

Technical & Architecture Governance

• Provide executive oversight across application modernization programs.
• Guide modernization strategies involving legacy Java and .NET applications, cloud migration, microservices adoption, API-led modernization, and platform transformation.
• Ensure adherence to enterprise architecture standards, security requirements, and regulatory compliance.
• Collaborate with architects and engineering leaders to resolve complex technical challenges.
• Establish modernization best practices, reusable frameworks, delivery accelerators, and governance standards.

Leadership & Organizational Development

• Build, mentor, and develop delivery managers, program managers, architects, and engineering leaders.
• Establish a culture of accountability, innovation, customer obsession, and delivery excellence.
• Support hiring, onboarding coaching, succession planning, and performance development.
• Drive capability development across modernization, cloud, DevOps, platform engineering, and AI-enabled transformation services.
• Foster collaboration across global and distributed delivery teams.

Business Growth & Strategic Initiatives

• Partner with sales and solution teams during pre-sales engagements.
• Support strategic solutioning, transformation workshops, executive presentations, and proposal reviews.
• Identify expansion opportunities within existing client accounts.
• Contribute to practice growth strategies and modernization offerings.
• Represent the organization as a trusted modernization advisor and thought leader.

Required Experience & Knowledge

• 15+ years of experience in software engineering, enterprise technology, or digital transformation.
• Minimum 8+ years leading enterprise-scale delivery programs.
• Proven experience delivering large Application Modernization and Cloud Transformation initiatives.
• Strong understanding of modernization approaches including:
• Rehost (Lift & Shift).
• Replatform.
• Refactor
• Rearchitect
• Rebuild
• Replace
• Experience with .NET and/or Java modernization programs.
• Experience managing multi-vendor, distributed, and global delivery teams.
• Demonstrated success managing executive stakeholders and steering committees.
• Strong experience in program governance, portfolio management, and delivery operations.
• Experience with Agile, SAFe, Hybrid, and Traditional delivery methodologies.
• Experience delivering within Banking, Financial Services, Insurance, Healthcare or other regulated industries.
• Strong understanding of DevSecOps, CI/CD, Cloud Engineering, and Platform Modernization.

Technical Expertise

Application Modernization

• Legacy application assessment and rationalization
• Microservices transformation
• API modernization
• Event-driven architectures
• Legacy-to-cloud migration
• Monolith decomposition
• Amazon Web Services (AWS)
• Containers & OpenShift
• Infrastructure as Code (Terraform, CloudFormation)
• DevSecOps
• Observability & Monitoring Platforms
• Executive Presence
• Strategic Thinking
• Customer Relationship Management
• Large Program Management
• Organizational Leadership
• Team Development & Coaching
• Business Growth & Account Expansion
• Cross-functional Collaboration

Qualifications

• Bachelor's degree in Computer Science, Engineering, Information Technology, or related field.
• Master's degree (MBA or Technology Management) preferred.