Senior Director, Technology, Business Systems & Integration

Role Overview

We Insure is seeking a Senior Director of Technology, Business Systems & Integration to lead our enterprise technology strategy through a pivotal modernization phase. This leader will own the vision and execution of the technology roadmap, upgrading legacy systems, integrating cloud-based platforms, leveraging AI-driven solutions, and ensuring seamless data flow across all core business applications.

This is a hands-on leadership role overseeing a team of up to four engineers and managing key vendor partnerships. The ideal candidate brings a builder mindset, combining strategic vision with a roll up your sleeves approach to design, build, and scale modern solutions. They have a proven record of driving technology transformation, executing complex integrations, and aligning technology and AI initiatives with business outcomes in a fast paced, growth oriented environment

Location: Austin, TX (Hybrid)

Key Responsibilities

Technology Strategy and Roadmap

• Develop and execute a modernization roadmap aligned with business goals

• Reduce system silos and create real time data connectivity.

• Leverage technology to improve efficiency, strengthen customer experience, and enable smarter decisions.

• Present strategy and progress to executive leadership.

Builder Mindset and Execution

• Combine strategic vision with hands on delivery to build scalable, future ready systems.

• Architect and implement modern solutions that replace legacy systems and drive efficiency.

• Establish frameworks and tools that support growth and agility.

• Foster a culture of ownership, innovation, and continuous improvement

Commercial Acumen and Business Alignment

• Connects technology strategy to sales, customer experience, and overall business outcomes.

• Skilled at bridging technical and business language, clearly articulating the “why” behind architecture and modernization decisions.

• Evaluate build vs. buy decisions, reduce tech debt, and ensure technology investments deliver measurable ROI.

• Understands how technology modernization supports growth, efficiency, and competitive advantage.

Project Leadership and Roadmap Execution

• Provide hands on leadership in delivering cross-functional initiatives, migrations, and enterprise platform rollouts.

• Drive technology transformation by aligning system improvements with business goals and employee needs.

• Manage portfolio of initiatives (system integrations, vendor implementation, and application deployment using agile best practices.

• Ensure projects are delivered on time, within budget, and in alignment with business priorities.

Systems Integration and Architecture

• Oversee the integration of core systems (Applied Epic AMS, InsuredMine CRM, comparative raters, telephony, data warehouse, etc.).

• Guide and design enterprise/business system integrations that reduce data silos, improve accuracy, and ensure seamless information flow.

• Evolve enterprise architecture by moving from legacy/monolithic systems toward more flexible, service oriented designs.

Process Automation and Optimization

• Identify gaps not met by vendor platforms and close them through workflow automation, APIs, or lightweight tools.

• Oversee delivery of dashboards, reporting tools, or RPA solutions that improve efficiency and access to real time data.

• Ensure all solutions are scalable, reliable, and integrated into the broader enterprise architecture.

AI -Driven Technology Solutions

• Lead the rollout of AI chatbots and call routing tools that cut call times and give customers faster, smoother service.

• Use AI to automate repetitive tasks, streamline workflows, and fill gaps our vendor platforms don’t cover.

• Implement AI to clean up data and deliver predictive insights that help the business make smarter, faster decisions.

Vendor Management

• Act as primary liaison with technology vendors (Applied Epic, InsuredMine, etc.)

• Evaluate third party solutions and negotiate contracts in collaboration with procurement.

• Hold vendors accountable to commitments and advocate for enhancements (e.g., APIs, franchise specific features).

Cloud Infrastructure and Security

• Oversee cloud infrastructure (primarily AWS) for reliability, scalability, and security.

• Coordinate with IT/security resources on data protection, backups, and compliance with insurance data regulations.

• Ensure high availability standards across the integrated environment.

Metrics and Reporting

• Define and track KPIs for technology operations (e.g., ROI, adoption rates, uptime, response times).

• Provide transparent updates to leadership and franchises on progress and impact.

• Use data to drive decision making and continuous improvement.

Experience Needed

• Strong background in enterprise/business systems and integrations, including CRM, telephony, and data warehouse platforms.

• Proven track record modernizing frameworks and moving from legacy to secure, scalable, service-oriented architectures.

• Demonstrated ability to deliver measurable gains in efficiency, scalability, and reliability.

• Skilled at linking technology strategy to sales, customer experience, and business outcomes, and influencing executives with clear communication.

• Leadership in cross-functional initiatives, migrations, and enterprise platform rollouts.

• Implementation of AI technology solutions with proven results, such as chatbots, call routing, or predictive analytics, that reduce manual work, improve data quality, and enhance customer experience.

Education

• Bachelor’s degree in information systems, Computer Science, Engineering, or a related field required.

• Advanced degree or relevant certifications (e.g., Enterprise Architecture, Cloud, Project Management) are a plus but not required.