Director Of Information Technology

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Overview

Director Of Information Technology Position purposeThe Director of Information Technology owns the strategy, people, reliability, security,

Technical Tools

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→Lead, coach, and hold the IT team accountable through clear roles, development plans, weekly operating rhythms, and honest performance conversations.
→Build redundancy and a documented knowledge base so critical knowledge never depends on one person.

Own store networks, connectivity, POS hardware, payment devices, and the support model that keeps 40+ cafes running during operating hours.
Set monitoring, escalation, and service-level standards; use ticket data to remove root causes instead of repeating manual fixes.

Own the business and technical health of the Square ecosystem: POS, payments, loyalty, menus, pricing, and permissions.
Partner with Marketing on the mobile app, loyalty, and digital ordering, and with Finance on settlement, reporting, and system integrations.

Run a risk-based security program: identity and access, multifactor authentication, endpoint and device management, and timely access removal.
Maintain PCI DSS and California privacy compliance; own incident response, disaster recovery, and executive communication during material events.

Deliver technology readiness on time for every new store opening, remodel, and rollout using repeatable checklists, testing, and cutover plans.

Stand up and lead our AI and automation program, building it into a governed function targeting 5 to 10 hours saved per employee per week.
Establish ownership for data quality, integrations, and the responsible, secure use of AI tools across the company.

Maintain a practical technology roadmap aligned with growth and profitability; advise executives on risk, tradeoffs, and return in business terms.
Own vendor contracts, negotiations, and performance; build and manage the IT operating and capital budgets with visible cost discipline.

8+ years of progressive IT experience, including 3+ years directly leading and developing people. People development is weighted above technical depth in this seat.
Success supporting distributed, multi-unit retail, restaurant, or hospitality operations.
Working knowledge across POS and payments, store networking, endpoint and identity management, cloud applications, and cybersecurity fundamentals.
Experience leading new location openings, system rollouts, integrations, and incident response.
Experience managing budgets, vendors, managed service providers, and technology contracts.
Clear communication of technical risk and options to executives and non-technical operators.
Bachelor's degree in a related field or equivalent experience; valid driver's license and ability to travel to cafes, including occasional early mornings, evenings, or weekends.

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Square platform experience, or comparable QSR/cafe ecosystems; restaurant loyalty, mobile app, and digital ordering platforms.
PCI DSS, California privacy, disaster recovery, and cyber insurance experience.
Experience scaling technology in a growing brand of 25 to 100+ locations within lean, cost-disciplined operators.
Relevant certifications such as ITIL, PMP, CISSP, or CISM; practical experience with data platforms, APIs, and governed AI adoption.