Assistant Director IT Applications Development

HAI Group · Cheshire, CT

Posted 8/3/2026 · last confirmed live 8/26/2026

Position Overview The assistant director, application development provides leadership for the application development function and helps shape the design, delivery, support, and ongoing evolution of technology solutions that meet HAI Group business needs. This role leads development teams while also engaging deeply in the systems, platforms, and engineering practices that support secure, scalable, high-quality application delivery. The Assistant Director strengthens development standards, DevSecOps discipline, delivery practices, and governance approaches while promoting operational excellence and continuous improvement. The assistant director, application development operates with both strategic perspective and strong technical engagement, helping develop talent, balance priorities across multiple initiatives, and align delivery with enterprise goals. This role partners closely with business leaders, product management, architecture, infrastructure, security, and operations teams to guide solution direction, improve delivery effectiveness, and ensure strong support for HAI Group’s enterprise production applications and critical business platforms. This position plays a key role in HAI Group’s transition to new platforms and solutions, including the OneShield platform and a mix of internally developed and third-party technologies. The successful candidate will engage deeply in existing applications and engineering practices to support critical operations while helping build the internal capabilities needed to support, enhance, and evolve new platforms over time. This role will work closely with vendors, strengthen collaborative delivery and support models, shape integration strategies, and partner with business teams and analysts to guide future-state solution design. Essential Functions Technical Leadership & Delivery Provides strong technical leadership for the development organization and drives continuous improvement across engineering, DevSecOps, release, security, and operational capabilities. Leads development teams within a SAFe Agile environment to iteratively design, develop, test, and deliver high-quality solutions, partnering with product management to refine initiatives, epics, and stories. Builds strong partnerships with business leaders and product management to align priorities, communicate progress, and guide delivery decisions across all levels of the organization. Provides technical and operational leadership across the development portfolio, including setting priorities, balancing resources, and ensuring consistent, high-quality delivery. Delivery, DevOps & Quality Drives the advancement of DevOps practices by leading development efforts and partnering with infrastructure and operations teams to improve automation, deployment workflows, and delivery efficiency. Partners with QA to ensure solutions are designed for quality, testability, and reliable delivery. Ensures the development organization operates within defined processes and governance standards while continuously improving engineering methodology, delivery practices, and operational effectiveness. Promotes ongoing technical growth across the team through adoption of relevant technologies, practices, and approaches. Architecture, Platforms & OneShield Provides direction, coordination, and collaboration for overall solutions architecture, working closely with the CTO and key stakeholders to guide platform, integration, and technical design decisions in support of business and enterprise priorities. Shapes and evolves solution architecture across platforms and integrations to support changing business needs and enterprise strategy. Leads the build-out and strengthening of application development and support capabilities for the OneShield platform by developing internal expertise while fostering a strong, collaborative vendor partnership to operate as a unified team for delivery, support, and ongoing platform evolution. Serves as a key contributor to technical strategy and solution design, leading and advising on architectural decisions and maintaining appropriate documentation. Business Alignment & Cross-Functional Collaboration Works closely with business leadership and product management to analyze requirements and ensure solutions effectively support business objectives. Collaborates with infrastructure and security teams to ensure solutions are scalable, secure, and aligned with performance, capacity, and lifecycle considerations. Production Support & Service Performance Accountable for the support, stability, and continuous improvement of HAI Group production applications. Leads root cause analysis for technical issues and drives lasting improvements to application reliability, stability, and performance. Partners with the HAI Group Service Desk to ensure responsive, high-quality application support. Monitors service performance against SLAs and KPIs, driving continuous improvement and evolution of service measures. Job Requirements Bachelor’s Degree in computer engineering or related field; or equivalent work experience 7+ years of leadership experience in application development, software delivery, and/or technology management, including responsibility for teams, priorities, and delivery outcomes. 5+ years of experience in property and casualty insurance technology, preferably within an application development or enterprise systems environment. 10+ years of experience in application development within client/server, web, service-oriented, or modern cloud-enabled environments, including significant success leading strategic technology initiatives and delivering solutions. Experience with Microsoft development platforms preferred. 7+ years of experience working with application data and enterprise data platforms, including relational databases such as Microsoft SQL Server or comparable technologies. Must be able to be on-site for two weeks for training upon hire in our Cheshire, CT office Must be legally authorized to work in the United States without the need for employer sponsorship, now or at any time in the future. Knowledge, Skills, Abilities Knowledge Strong knowledge of property and casualty insurance business operations and supporting technology needs preferred. Strong knowledge of enterprise application development tools, platforms, delivery methodologies, and engineering governance practices. Well-versed in Agile software delivery methodologies such as SAFe or Scrum, with strong practical experience applying them in delivery environments. Strong working knowledge of infrastructure, cloud-based platforms, and security practices that support enterprise application delivery and operations Strong experience with service-oriented and integration-based architectures, including modern APIs, enterprise integration patterns, and supporting technologies. Strong experience with application data structures and patterns across different forms, formats, and platforms, including how data is managed, transformed, and integrated. Skills Analytical and problem-solving skills; seeks solutions to customer challenges Communication (questioning/listening) and responding clearly (verbal and written) Team player; builds trusting relationships Excellent organizational skills and time management abilities are essential Talent Effectively leads multiple concurrent initiatives of moderate to high complexity while balancing strategic priorities, operational needs, and organizational constraints. Adapts quickly to changing priorities and responds with urgency, judgment, and focus. Demonstrates curiosity about how technology solutions contribute to business outcomes. Seeks out best practices and applies lessons learned to improve outcomes. Coaches and develops leaders and team members, fostering accountability, engagement, collaboration, and strong performance across the development organization. Work Environment and Physical Demands Inside climate-controlled office building Prolonged sitting and using a PC <10% Travel Ability to lift 25lbs Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice. Department Overview The Information Technology Department works closely with internal and external business partners using their subject matter expertise to strategically invest in information systems and infrastructure across the enterprise. Flexible and adaptive to customer needs, the IT Team takes a broad view of the HAI Group enterprise; contributing research and development to strengthen and add value to business operations. IT develops its team in both the technical and leadership career paths to support customers while meeting the development needs of the team. Highly responsive, the team continually explores best practices and their application to growing the HAI Group enterprise. Company Overview  HAI Group® [1] ,  is the nation’s leading property-casualty insurance company founded by and dedicated to affordable housing organizations. While we are recognized as a pioneer of affordable housing insurance programs, insurance is not our only strength. We protect, preserve, and promote the sustainability of affordable housing with an array of products and services that support the challenges housing organizations face. Besides insurance, we offer risk management services, online training, and consulting services used by more than 1,500 housing organizations nationwide. Headquartered in Cheshire, Connecticut, HAI Group® was recognized as a Top Workplace from 2020-2025. Cultural Objective HAI Group contributes to a culture that creates a safe and healthy working environment and a space of inclusiveness and belonging for all by: exceeding our customers’ expectations, working collaboratively across the organization, embracing diversity, and demonstrating mutual respect and empathy.   HAI Group Benefits and Perks Bonus program eligibility Annual merit increase program Outstanding 401(k) plan with match and additional non-elective company contributions Flexible work schedules Generous paid time off including paid volunteer days and holidays Medical, vision and dental Insurance Company paid life, AD&D, short-term disability, and long-term disability coverage HSA, and Health and Dependent Care FSA options On-Site wellness: Full gym and locker rooms, private wellness room (featuring a massage chair, lounge area, vibration plate, and a refrigerator, with accommodations for use as a private lactation space), wellness initiatives, outdoor basketball and tennis/pickleball courts, walking trail, picnic pavilion area Tuition reimbursement and student loan repayment program Professional development  Community outreach HAI Group is an Equal Opportunity Employer. HARRG Inc., reserves the right to fill this position at a level above or below the level included in this posting. No agency submissions please. Resumes submitted to any HAI Group employee without a current, signed, and valid contract in place with the HAI Group Recruiting team for this position will become the property of HAI Group and no agency fees will be paid. HAI Group's Notice of Collection of Personal Information: https://resources.haigroup.com/hubfs/2023-HAI-Notice-of-Collection-Employees_1099_Applicants.pdf   [1] HAI Group® is a marketing name used to refer to insurers, a producer, and related service providers affiliated through a common mission, management, and governance. Property-casualty insurance and related services are written or provided by Housing Authority Risk Retention Group, Inc.; Housing Authority Property Insurance, A Mutual Company; Housing Enterprise Insurance Company, Inc.; Housing Specialty Insurance Company, Inc.; Innovative Housing Insurance Company Inc.; Housing Investment Group, Inc.; and Housing Insurance Services, Inc. (DBA Housing Insurance Agency Services, Inc. in NY and MI).  

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