Director of Application Delivery/Engineering

Location: Cincinnati (hybrid in office 40-50%) will consider remote candidates near Cincinnati 

The Head of Sub Section – Application Development is a technology and people leader accountable for driving end-to-end delivery, modernization, and automation across a complex application landscape. This role is carries direct responsibility for building, leading, and sustaining high performing application development teams while ensuring delivery excellence across highly technical initiatives.  This role is responsible for delivering scalable, secure, and resilient application solutions while developing talent, setting clear expectations, and fostering a culture of accountability, continuous improvement, and engineering excellence. This role partners closely with business leaders, architecture, security, and operations to modernize the portfolio and improve speed-to-value, with a strong emphasis on platform-first decision making, sustainable engineering, and strong people leadership.

Key Accountabilities

Delivery & Execution

• Own delivery outcomes for highly technical, multi‑stream application initiatives, ensuring predictable execution, quality, and business value realization.

• Drive modern delivery models (product-centric, agile, DevSecOps) with strong engineering discipline and operational rigor.

• Ensure delivery transparency, dependency management, and proactive risk mitigation across the application portfolio.

• Ensure high-quality solution design and readiness (architecture, APIs, integrations) prior to execution to avoid rework and delivery friction.

• Prioritize delivery across investment projects, production support, and regulatory commitments to optimize outcomes and reduce operational risk.

• Remove delivery blockers, resolve dependencies, and escalate risks early to protect timelines, quality, and business outcomes.

• Navigate and resolve tension between delivery teams, business urgency, and compliance requirements through clear decisioning, trade-off transparency, and disciplined governance.

Modernization, Platforms & Automation

• Drive technical delivery of transformational and modernization efforts including cloud-native architectures, API enablement, platform re‑engineering, and legacy rationalization.

• Work with architecture and technical leadership to make deliberate build‑vs‑configure‑vs‑integrate decisions for PaaS platforms (e.g., Guidewire, Duck Creek), minimizing customization and preserving upgradeability, performance, and vendor alignment.

• Champion automation across the SDLC (CI/CD, testing, deployment, environment provisioning, monitoring).

• Reduce technical debt and operational friction through standardization, reuse, and platform leverage.

Integration& Engineering Excellence

• Establish strong integration discipline, ensuring APIs are well-designed, documented, versioned, and aligned to enterprise integration standards.

• Provide technical leadership across complex platform and cross-system integrations (e.g., IAM/CIAM, data platforms, external services).

• Foster an innovation mindset by introducing modern engineering practices, tools, and patterns while maintaining enterprise-grade controls for security, resiliency, and compliance.

• Establish and enforce engineering standards aligned with enterprise architecture, security, and risk policies.

People & Capability Leadership

• Build, lead, and develop high-performing application development teams with deep technical expertise.

• Set clear expectations for technical leadership, accountability, and continuous improvement.

• Drive skills uplift in modern technologies, cloud platforms, automation, and platform engineering.

• Assign and flex technical resources across investment projects and operational priorities to maximize throughput, reduce bottlenecks, and meet delivery commitments.

Stakeholder,Governance& Partner Management

• Act as a trusted technology partner to business leaders, translating needs into executable, platform-aligned solutions.

• Proactively orchestrate cross‑tower dependencies (Architecture, Security, Infrastructure, IAM, Operations) to ensure coordinated and timely delivery.

• Ensure application delivery complies with enterprise SDLC, security, and change governance requirements, while actively removing unnecessary friction.

• Ensure applications meet security, audit, and regulatory expectations through strong controls, evidence-based delivery, and continuous compliance practices.

• Lead cross-functional delivery teams, including effective management of access roles and entitlements required to build, release, and operate applications securely.

• Manage strategic vendors and system integrators to ensure delivery quality, architectural alignment, and value realization.

Required Experience & Qualifications

• 12+ years of progressive experience in application development and engineering leadership.

• Proven success leading complex, highly technical initiatives across enterprise platforms.

• Strong background in modern application architectures (cloud, APIs, microservices, event-driven systems).

• Hands-on experience with Application Development, DevSecOps, CI/CD pipelines, and automation frameworks.

• Demonstrated ability to modernize legacy platforms while maintaining business continuity.

• Experience building on, extending, and integrating with insurance PaaS platforms (e.g., Guidewire, Duck Creek), including configuration, customization, API-based integration, and alignment to vendor roadmaps.

Leadership & Behavioral Expectations

• Outcome-driven with a strong bias for action, accountability, and delivery.

• Provides credible technical leadership; able to challenge designs, evaluate trade-offs, and guide teams toward sound engineering decisions.

• Comfortable operating in ambiguity and driving change across entrenched landscapes.

• Balances innovation with operational excellence, security, and risk management.

• Acts as a role model for collaboration, transparency, and continuous improvement.

• Able to bridge business strategy and technical execution—translating objectives into clear roadmaps, sequencing, and engineering decisions.