Head of Enterprise Technology & AI Transformation

Swooped; United States; Hybrid; USD 210,000 - 270,000; Full time

Benefits offered by this job

Equity

Generous PTO

401k match

Parental leave

Job summary

Pie Insurance is looking for a bold, strategic Chief Enterprise Technology Officer to scale Business Systems and Corporate IT in a fast-growing insurance tech company. You will drive long-term technology strategy, align initiatives with business goals, and lead cross-functional teams to deliver secure, scalable systems.

The role emphasizes AI-driven automation, master data management, and strong cybersecurity; hybrid/remote work in the United States is supported, with offices in Denver as an

Qualifications

• Bachelor’s Degree required; MBA or relevant advanced degree preferred.
• 15+ years of technology leadership in fast-paced, high-growth environments.
• 7+ years of executive-level experience managing enterprise systems, IT, or similar disciplines.
• Proven ability to drive complex technology strategies and initiatives, including large-scale system implementations, integrations, and data governance.
• Deep understanding of AI technologies and their application in enterprise environments.
• Advanced communication, stakeholder management, and change leadership skills.

Responsibilities

• Define and execute a long-term strategy for enterprise technology that aligns with Pie’s broader business goals.
• Deeply understand Pie’s operational challenges and design technology solutions that address them with measurable impact.
• Lead the adoption of AI technologies across business functions to streamline operations and improve cost-efficiency.
• Build platforms and capabilities that drive both procedural and technical enhancements organization-wide.
• Lead the implementation of master data management and enterprise system integrations using scalable and sustainable architectural patterns.
• Establish and scale an Enterprise Architecture and IT Governance practice.
• Oversee and ensure a comprehensive enterprise Cybersecurity program, including policy development, incident response, and compliance with relevant standards and regulations.
• Collaborate closely with other executives and senior functional leaders to align technology investments with strategic business priorities.
• Work hand-in-hand with Data Engineering, Software Engineering, and Product Management teams to ensure integrated and secure system designs.
• Partner with Legal, Risk, and Compliance to ensure all systems meet regulatory and security requirements.
• Build, lead, and mentor a high-performing Enterprise Technology organization including Business Systems, Corporate IT, and potentially other enabling technology functions.
• Cultivate a culture of innovation, operational excellence, and continuous improvement.
• Set clear goals and expectations, provide regular coaching and feedback, and support professional growth for all team members.

Skills

Technology leadership

Executive leadership

Stakeholder management

Change management

AI in enterprise

Strategic planning

Education

Bachelor's degree

MBA preferred

Tools

Salesforce

Workday

Middleware technologies

Enterprise data architecture

Job description

Pie Insurance is looking for a bold, strategic Chief Enterprise Technology Officer to scale Business Systems and Corporate IT in a fast-growing insurance tech company. You will drive long-term technology strategy, align initiatives with business goals, and lead cross-functional teams to deliver secure, scalable systems.

The role emphasizes AI-driven automation, master data management, and strong cybersecurity; hybrid/remote work in the United States is supported, with offices in Denver as an