Head of Information Technology & Business Systems

Head of Information Technology & Business Systems Build the Technology Foundation for the Next Generation of Our Marketplace

Autoland is a well-established, nationally recognized marketplace that connects consumers, financial institutions, and vehicles. Our history is established, but our mindset is entrepreneurial: we operate with the agility and ambition of a startup, backed by the stability and resources of a mature organization.

We are seeking a Head of Information Technology & Business Systems to lead the company's transition from internally developed applications to a modern, platform-based ecosystem. Reporting directly to the President & CEO, this leader will architect the systems, integrations, and data foundations that power the future of our digital marketplace, and will stay hands‑on in execution.

This is not a traditional infrastructure leadership position. Our day‑to‑day IT operations and end‑user support are delivered through managed service partners, keeping this role focused on business systems, integration, data architecture, and the platform transition. You will build the foundation for our next generation marketplace platform while leading a talented engineering team through a major evolution in how technology is delivered.

• Own the company's business systems ecosystem, including Salesforce and future platform investments.
• Define the data architecture, system-of-record ownership, and integration standards that let independent platforms share data reliably.
• Lead Salesforce implementation, administration, integrations, and data strategy, managing implementation partners and ensuring delivery quality, security adoption, and ROI.

• Lead the migration from proprietary software to modern SaaS and platform-based systems, sequencing cutovers with minimal business disruption.
• Ensure historical data remains available for reporting, compliance, and analytics.

• Evaluate and select platforms and vendors; negotiate and manage contracts and renewals; oversee the managed service providers responsible for IT operations and support.
• Manage the function's operating budget, including platform subscriptions, vendor contracts, and managed services spend.
• Own identity and access management, and partner with cybersecurity, compliance, and infrastructure stakeholders on business continuity, audit readiness, and privacy.

• Coach and develop a team transitioning from software development to platform engineering and systems integration.
• Evaluate automation, AI, and emerging technologies, implementing practical solutions with measurable business value.

• Bachelor's degree in Computer Science, Information Systems, Information Technology, Software Engineering, or equivalent practical experience.
• 8+ years of progressive experience in:
  Information Technology, Business Systems, Systems Integration, Software Engineering, or Data Architecture.
• 3+ years of experience leading and developing high-performing technical teams.
• Experience leading enterprise CRM, ERP, or business systems implementations.
• Hands‑on Salesforce experience including architecture, administration, integrations, or data migration.
• A track record of modernizing or replacing a proprietary or legacy platform, migrating its functions onto commercial platforms, including sequencing cutovers and managing the engineering work.
• Digital marketplace, fintech, e‑commerce, or B2B2C experience.
• Strong expertise in: APIs, integration platforms, data governance, cloud technologies, and cybersecurity best practices.
• Experience managing technology vendors and implementation partners.
• Strong communication and stakeholder…