🚀 Senior Director, Technology, Business Systems & Integration

Senior Director of Technology, Business Systems & Integration

Location: Austin, TX (Hybrid)

We Insure Group is seeking a Senior Director of Technology, Business Systems & Integration to lead our enterprise technology strategy through a 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 guiding key vendor partnerships. The ideal candidate brings strategic vision, proven execution, and the ability to align technology and AI initiatives with business outcomes in a fast-paced, growth-oriented environment.

Key Responsibilities

• Technology Strategy and Roadmap: Develop and refine a technology modernization roadmap aligned with business goals. Identify opportunities to reduce silos and create real-time connectivity across systems and data. Leverage technology to improve efficiency, strengthen customer experience, and enable smarter decision making. Present strategy and progress to executive leadership and company ownership.
• Commercial Acumen and Business Alignment: Connect technology strategy to sales, customer experience, and overall business outcomes. Bridge technical and business language, articulate the "why" behind architecture and modernization decisions. Evaluate build vs. buy decisions, reduce tech debt, and ensure investments deliver measurable ROI. Understand how 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 aligned with priorities.
• Systems Integration and Architecture: Oversee integration of core systems (Applied Epic AMS, InsuredMine CRM, comparative raters, telephony, data warehouse, etc.). Design enterprise integrations that reduce data silos, improve accuracy, and ensure seamless information flow. Evolve architecture toward flexible, service-oriented designs.
• Process Automation and Optimization: Identify gaps not met by vendor platforms and close them via workflow automation, APIs, or lightweight tools. Oversee dashboards, reporting tools, or RPA solutions that improve efficiency and access to real-time data. Ensure solutions are scalable and integrated into the broader enterprise architecture.
• AI-Driven Technology Solutions: Lead rollout of AI chatbots and call routing tools to reduce call times and improve service. Use AI to automate repetitive tasks, streamline workflows, and fill gaps not covered by vendor platforms. Implement AI to clean data and deliver predictive insights for better decision making.
• 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 and advocate for enhancements (APIs, franchise-specific features).
• Cloud Infrastructure and Security: Oversee cloud infrastructure (primarily AWS) for reliability, scalability, and security. Coordinate with IT/security on data protection, backups, and compliance with insurance data regulations. Ensure high availability across the integrated environment.
• Metrics and Reporting: Define and track KPIs for technology operations (ROI, adoption, uptime, response times). Provide transparent updates to leadership and franchises on progress and impact. Use data to drive decision making and continuous improvement.

Experience and Education

• 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.
• Ability to link technology strategy to sales and customer experience, and influence executives with clear communication.
• Leadership in cross-functional initiatives, migrations, and enterprise platform rollouts.
• Experience implementing AI technology solutions with measurable results (e.g., chatbots, call routing, predictive analytics).

• 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.

Our Values and Benefits

Our Values : We personalize protection at a price you can trust, hustle to find opportunity, care authentically, thrive in ambiguity, own our results, have fun, and stay just getting started.

• Medical, Dental, Vision, Life, FSA
• Competitive Salaries
• 401K Match
• Work-Life Balance: Personal Days, PTO, 12 Paid Holidays, Volunteer Days, Paid Parental Leave
• Disability and Employee Support Programs, Including Mental Health
• Tuition Reimbursement
• Charitable Giving and Referral Programs

EEO and Disability : We Insure Group is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. We provide reasonable accommodations during the application process.

This position is not able to be performed in California, Colorado, New York or Washington.