Director of Application Development

Gallagher•Rolling Meadows, IL

About The Position

The Director of Application Development is responsible for leading custom application development across the Affinity technology portfolio. Reporting to the Affinity CIO, this role provides leadership across engineering teams supporting modern web and enterprise application platforms, with accountability for delivery execution, engineering quality, release governance, talent development, and operational support. The Director of Engineering works closely with product, program, architecture, operations, and business stakeholders to deliver scalable, secure, and reliable technology solutions aligned to business priorities. This role combines strong engineering leadership with disciplined execution. The Director of Engineering is responsible for establishing consistent delivery practices, strengthening team capability, improving development effectiveness, managing capacity and resource planning, and advancing the adoption of modern engineering approaches, including AI-enabled development patterns and automation. The role partners with enterprise architecture on solution direction while ensuring effective implementation within Affinity engineering teams and clear communication of delivery status, risks, and recommendations to senior leadership.

Requirements

Bachelor’s degree in Computer Science, Information Technology, Engineering, or a related field, or equivalent combination of education and experience.
Minimum of 10 years of progressive software engineering experience, including leadership responsibility across multiple teams or functions.
Demonstrated experience leading engineering managers, technical leads, or multi-team delivery organizations.
Strong experience with modern application development practices, agile software delivery methodologies, software development life cycle governance, and engineering quality management.
Experience working within cloud-based technology environments, including Microsoft Azure.
Experience leading teams delivering custom applications and integrations across enterprise application platforms, APIs, web applications, and data-driven solutions.
Proven ability to operate effectively in a matrixed environment and collaborate across business and technology functions.
Strong written and verbal communication skills with the ability to communicate delivery status, risk, and recommendations to senior leadership, executive stakeholders, and technical teams.

Nice To Haves

Experience with AI-enabled engineering tools and platforms such as Microsoft Copilot, Claude, or ChatGPT, and the ability to apply them effectively within software delivery practices.
Experience supporting custom application ecosystems that may include content management, integration, CRM, analytics, and cloud data platforms.
Experience with Microsoft-based engineering environments, Azure DevOps, CI/CD pipelines, automated testing, and release automation practices.
Experience in insurance, financial services, healthcare, or other regulated industries.
Familiarity with compliance, security, data protection, and audit considerations relevant to enterprise technology delivery.

Responsibilities

Lead end-to-end engineering delivery across custom application development teams, including planning, estimation, detailed scheduling, delivery cadence, release management, deployment coordination, production readiness, and post-release stabilization.
Provide leadership and direction on delivery priorities, risks, dependencies, and trade-off decisions to support successful execution across the portfolio.
Monitor and improve engineering performance through the use of delivery metrics, including throughput, cycle time, defect trends, release stability, and support effectiveness.
Manage engineering capacity, resource planning, vendor utilization, and budget considerations across the supported portfolio.
Ensure appropriate support and continuity for business-as-usual work, production issue resolution, Tier 3 application support activities, and after-hours operational support when required.
Contribute directly to delivery activities when needed to support team outcomes and business commitments.
Lead, coach, and develop engineering managers, technical leads, and engineering team members to build a high-performing organization.
Drive talent strategy across the function, including workforce planning, hiring, onboarding, performance management, succession planning, and career development.
Strengthen leadership depth and team resiliency by developing internal capability and reducing dependency on individual contributors.
Partner with technical product, business analysis, and program leadership to promote strong collaboration, backlog readiness, and effective delivery execution.
Oversee contractor and vendor contributions to ensure quality, continuity, and alignment with organizational expectations.
Establish and maintain engineering standards, development practices, quality controls, and release governance across supported application platforms.
Ensure engineering practices and supported solutions comply with enterprise technology policies, security requirements, audit expectations, and applicable control frameworks.
Partner with architecture, infrastructure, and security teams to ensure solutions are implemented in accordance with enterprise standards, platform requirements, compliance/security obligations, and technology roadmaps.
Advance engineering maturity through agile delivery practices, improved testing approaches, automation, CI/CD capabilities, developer experience, and continuous improvement initiatives.
Promote the effective use of AI-enabled development tools and automation to improve engineering efficiency, quality, and delivery outcomes.
Partner with program, product, and business stakeholders to support intake, prioritization, capacity planning, and release planning for engineering work.
Provide engineering leadership input to portfolio planning, sequencing, dependency management, delivery forecasting, and resource planning discussions.
Represent the engineering function in cross-technology forums, governance processes, leadership discussions, and executive-level briefings.
Build effective working relationships across business, technology, infrastructure, security, and operational teams to ensure alignment, transparency, and delivery success.

Benefits

Medical/dental/vision plans, which start from day one!
Life and accident insurance
401(K) and Roth options
Tax-advantaged accounts (HSA, FSA)
Educational expense reimbursement
Paid parental leave
Digital mental health services (Talkspace)
Flexible work hours (availability varies by office and job function)
Training programs
Gallagher Thrive program – elevating your health through challenges, workshops and digital fitness programs for your overall wellbeing
Charitable matching gift program