Director, Solutions Delivery (4791)

Purpose of Position:

The Director of Solutions Delivery is responsible for leading end to end technical delivery of CHOICE Administrators' mission-critical business and digital solutions, including Software-as-a Service (SaaS) solutions, commercial-off-the-shelf (COTS) applications, custom-built or enhanced applications, and end-to-end systems interoperability and integrations. Reporting directly to the Vice President of IT, the Director is expected to bring a balanced blend of deep technical expertise, strong delivery leadership, and outstanding cross-functional collaboration while leading technical solutions delivery managers and partnering closely with Architecture, Application Development & QA, IT Operations, Program Management, and senior business stakeholders to drive integrated execution of high impact transformation initiatives.

Essential Functions:

Strategy & Business Partnership

• Align solutions delivery priorities to support application modernization and digital transformation initiatives in alignment with organizational goals and strategic objectives.
• Identify opportunities to leverage AI, automation, and emerging technologies to improve productivity, quality, customer experience, and operational performance.
• Lead the evaluation, pilot, and scaling of emerging technologies and innovative solutions.
• Serve as a trusted advisor on technology opportunities, constraints, and tradeoffs in areas supporting CHOICE Administrators’ operations such as quoting, enrollment, billing, integrations, analytics, and broker/consumer digital experience.
• Partner with business, technology and operations leaders to translate strategy and regulatory requirements into executable technology roadmaps; and drive the creation of Level of Effort (LOE) estimates for technology initiatives in collaboration with Program Management Department.
• Maintain clear, proactive communication (verbal and written) with executives and cross-division leaders/stakeholders, including regular delivery of status updates and key decisions.
• Build and maintain strong partnerships across internal teams and external service providers to support coordinated delivery and operational alignment.

Solutions Delivery & Execution

• In collaboration with Architecture, Application Development & QA, and IT Operations, provide hands-on technical leadership across application architecture, design and engineering, systems and data integration, infrastructure and operations to drive high-quality and on-time end-to-end technical delivery of high impact transformational initiatives and technology modernization programs within planned resource allocation.
• Build and maintain deep subject-matter expertise in CHOICE Administrators’ technology solutions’ capabilities, business purpose, systems architecture, interoperability, and integration points.
• Lead multiple concurrent initiatives with complex dependencies and competing priorities across custom development, SaaS platforms, system integrations, and data solutions.
• Effectively manage blended delivery models with internal staff, offshore teams, and strategic vendors in a matrixed environment, and serve as a technical coach and escalation point for complex delivery issues.
• Drive disciplined delivery using modern methodologies (Agile, SAFe, hybrid) while ensuring predictable execution and measurable outcomes.
• Establish technical delivery standards/best practices, metrics, and governance to ensure on-time and high-quality releases.
• Balance speed and innovation with reliability, security, and regulatory compliance.
• Perform other solutions delivery oversight related tasks or functions as assigned.

Architecture, Quality & Operational Readiness

• Collaborate with Architecture, Application Development & QA, IT Operations and Security teams to ensure solutions are scalable, resilient, and aligned with technology standards.
• Ensure solutions meet performance, availability, supportability and operational readiness requirements prior to production deployment.
• In collaboration with Application Development & QA, drive continuous improvement in delivery velocity, quality, reliability, and deployment confidence with the advancement of DevSecOps practices, CI/CD pipelines, and intelligent QA automation.

Vendor Technical Delivery Management

• Oversee technical delivery commitments and performance of technology vendors, implementation partners, and systems integrators.
• Negotiate and manage technical delivery scopes, timelines, and outcomes to maximize value from vendor relationships.
• Ensure vendor solutions align with architectural standards and long-term strategy.

Compliance, Security & Risk Management

• Ensure solutions adhere to organizational standards for security, compliance, documentation, and audit readiness, including HIPAA and data privacy requirements.
• Partner with Legal, Compliance, and Information Security teams to proactively manage risk by applying application security best practices and embedding security/privacy by design principles into all solution delivery efforts.
• Lead technical response planning for audits, incidents, and regulatory changes.

People Management & Culture

• Recruit, develop, mentor, and retain a high-performing Solutions Delivery team.
• Establish clear goals, performance expectations, and career development pathways to build organizational capability.
• Provide coaching, feedback, and support to elevate team performance; and address performance issues professionally and consistently, following organizational guidelines and progressive discipline processes.
• Support team readiness and organizational resilience through training, skill development, documentation and knowledge-sharing practices.
• Promote a positive, transparent, and collaborative working environment where diverse perspectives are valued.
• Foster an engaged and high-performing team culture of accountability, continuous improvement, innovation, and operational excellence.
• Ensure a high-performing remote-work-friendly environment for team and self with consistent and regular remote and on-site (as required) attendance.

Qualifications

Knowledge, Skills & Abilities Required:

Core Leadership Competencies

• Demonstrated success in driving results with active management and oversight of multiple enterprise initiatives in alignment with strategic business goals while minimizing negative operational and business impact.
• Proven experience in strategic planning, tactical execution, and operational excellence.
• Demonstrated ability to influence, collaborate, and lead across a highly matrixed corporate environment including executive stakeholders.
• Expertise in proactive conflict resolution, consensus building, and stakeholder management.
• Strong analytical, diagnostic, and problem-solving capabilities.

Technical Expertise

• Proven experience, with demonstrated success, operating in environments with hybrid SaaS, COTS, and custom-built solutions.
• Demonstrated success establishing innovation programs, technology incubators, proof-of-concept initiatives, or emerging technology evaluation processes.
• Experience in integrating AI capabilities into enterprise applications, business workflows, customer-facing solutions, and software development lifecycles.
• Proven ability to identify, evaluate, and scale emerging technologies while balancing business value, risk, governance, and security.
• Demonstrated hands-on leadership experience in technical delivery, solutions design, architecture and engineering, systems integration, and application modernization using enterprise-scale technology stacks (e.g., cloud computing, Microsoft .NET, SQL Server, REST/SOAP services, Azure DevOps), AI-assisted software development tools, AI-powered testing and quality engineering platforms, and intelligent process automation.
• Strong understanding of software design & architecture patterns (e.g., microservices, event-driven, serverless), integration frameworks, APIs and microservices, data interoperability frameworks, and security best practices.
• Strong working knowledge of SAFe, Agile, Waterfall and hybrid delivery methodologies, DevSecOps practices, CI/CD pipelines, and observability, monitoring, and performance engineering.
• Solid understanding of rules-based systems, business process engineering, automation and optimization tools.

Professional Skills

• Exceptional English written and verbal communication abilities, including stakeholder-facing documentation and communication with all levels of employees and partners.
• Ability to thrive in a dynamic, fast-paced environment with competing priorities.
• Experience leading globally distributed teams and vendor resources in a matrixed environment.

Preferred Experience

• Health insurance, healthcare technology, or other highly regulated industry experience.
• Deep understanding of HIPAA, PHI, PII compliance, and regulatory driven development.

Educational and Experience Requirements:

• Bachelor’s degree in computer science, engineering, or related field (or equivalent experience).
• 15+ years of progressive leadership experience in technical delivery, solutions design, architecture and engineering.
• AI, SCRUM, Cloud Solutions Architect certification preferred.

Physical Requirements:

• Ability to sit, type, and work at a computer for extended periods.
• Adequate hearing and vision to perform essential job functions.
• Ability to use standard office equipment and lift up to 40 pounds occasionally.
• On call availability as needed.