Director Of Information Technology
About The Position
The Director of Information Technology owns the strategy, people, reliability, security, and continuous improvement of the technology ecosystem supporting 7 Leaves Cafe’s 35+ locations, planned store growth, and AI and automation program. This is a hands-on leadership role in a lean, disciplined operating environment, with a strong emphasis on developing people, coaching a small technical team, building bench strength, and ensuring critical systems and knowledge do not depend on a single person. The Director leads IT team development and operating practices; owns cafe technology reliability, including networks, connectivity, POS hardware, payment devices, and support standards; and oversees the Square ecosystem and digital guest experience in partnership with Marketing and Finance. The role also leads cybersecurity, privacy, incident response, disaster recovery, and executive communication during material events. The Director delivers technology readiness for store openings, remodels, and rollouts; establishes a governed AI and automation program intended to save 5 to 10 hours per employee per week; and sets ownership for data quality, integrations, and responsible AI use. The role maintains a practical technology roadmap, advises executives on risk and business tradeoffs, manages vendors and contracts, and develops and oversees IT operating and capital budgets.
Requirements
- At least 8 years of progressive IT experience, including at least 3 years directly leading and developing people.
- Experience supporting distributed, multi-unit retail, restaurant, or hospitality operations.
- Working knowledge of 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.
- Ability to communicate technical risks and options clearly 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.
Nice To Haves
- Experience with the Square platform or comparable QSR/cafe ecosystems, restaurant loyalty, mobile app, and digital ordering platforms.
- Experience with PCI DSS, California privacy, disaster recovery, and cyber insurance.
- 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.
Responsibilities
- Lead, coach, and hold the IT team accountable through clear roles, development plans, weekly operating rhythms, and performance conversations.
- Build team redundancy and a documented knowledge base so critical knowledge does not depend on one person.
- Own store networks, connectivity, POS hardware, payment devices, and support for cafes during operating hours.
- Set monitoring, escalation, and service-level standards, and use ticket data to address root causes.
- Own the business and technical health of the Square ecosystem, including 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 integrations.
- Run a risk-based security program covering identity and access, multifactor authentication, endpoint and device management, and timely access removal.
- Maintain PCI DSS and California privacy compliance, and own incident response, disaster recovery, and executive communication during material events.
- Deliver technology readiness for every new store opening, remodel, and rollout using repeatable checklists, testing, and cutover plans.
- Stand up and lead a governed AI and automation program targeting 5 to 10 hours saved per employee per week.
- Establish ownership for data quality and integrations, and guide responsible, secure AI tool use across the company.
- Maintain a technology roadmap aligned with growth and profitability, and advise executives on risk, tradeoffs, and return in business terms.
- Own vendor contracts, negotiations, and performance.
- Build and manage IT operating and capital budgets with visible cost discipline.
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What This Job Offers
Job Type
Full-time
Career Level
Director
