VP, Enterprise Technology

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's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.

Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven bycore values and operating principles that guide every decision we make.

The Vice President, Enterprise Technology is responsible for leading and scaling the Business Systems and Corporate IT functions at Pie. This executive will drive enterprise technology strategy and execution, focusing on maximizing operational efficiency, enabling scalability, and improving cost-effectiveness through technology. A key responsibility will be driving the adoption of AI tools and systems to automate processes, augment workforce productivity, and reduce operational costs.

How You’ll Do It

• 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.

Leadership:

• 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.

The Right Stuff

• Bachelor’s Degree required; MBA or relevant advanced degree preferred.
• 15+ years of experience in technology leadership roles within fast-paced, high-growth environments.
• 7+ years of executive-level experience managing enterprise systems, IT, or similar disciplines in the insurance or financial services industry.
• 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.
• Experience with platforms such as Salesforce, Workday, middleware technologies, and enterprise data architecture.

Base Compensation Range

$210,000—$270,000 USD

• Competitive cash compensation
• A piece of the pie (in the form of equity)
• Generous PTO
• Future focused 401k match
• Generous parental and caregiver leave
• Our core values are more than just a poster on the wall; they’re tangibly reflected in our work

Our goal is to make all aspects of working with us as easy as pie. That includes our offer process. When we’ve identified a talented individual who we’d like to be a Pie-oneer , we work hard to present an equitable and fair offer.We look at the candidate’s knowledge, skills, and experience, along with their compensation expectations and align that with our company equity processes to determine our offer ranges.

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Location Information

Unless otherwise specified, this role has the option to be hybrid or remote. Hybrid work locations provide team members with the flexibility of working partially from our Denver office and from home. Remote team members must live and work in the United States* (*territories excluded), and have access to reliable, high-speed internet.

Additional Information

Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

Pie Insurance participates in the E-Verify program. Please click here, here and here for more information.

Pie Insurance is committed to protecting your personal data. Please review our Privacy Policy .

Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

Pie Insurance leverages data-driven technology to provide small businesses with competitive pricing and exceptional coverage in their insurance needs.