Executive Support Technician
Gap Inc. · SF
About the Role
As the Technology Assistant to the CEO specializing in iOS capabilities and new market innovations, you will be instrumental in supporting the CEO with advanced technology solutions tailored to iOS platforms and exploring cutting-edge innovations for business growth. This role requires deep native fluency in the Apple ecosystem, the judgment to navigate ambiguous, fast-changing priorities without direct daily access to the CEO, and the ability to distill complex technical concepts into clear, confident, simple guidance. You will integrate innovative AI solutions into the CEO's daily workflow to reduce friction and save time, while operating with the discretion required of someone entrusted with highly confidential information.What You'll Do
- iOS Technology Management:
- Support, manage and optimize iOS devices, applications, and ecosystems used by the CEO utilizing deep, native fluency in Mac tools (incl. Mail, Contacts, and Calendar).
- Ensure seamless integration and functionality across iOS platforms — Macs, iPads, iPhones — and their interoperability with enterprise Windows and O365 environments.
- Provide technical support and troubleshooting, ensuring swift resolution with minimal disruption to the CEO's day.
- New Market Innovations:
- Research and evaluate emerging technologies, AI tools, and market trends relevant to the CEO office's strategic goals.
- Identify opportunities for leveraging new software, technologies, and AI solutions to enhance productivity, efficiency, and competitive advantage.
- Pilot and implement innovative solutions, collaborating with internal teams and stakeholders to drive adoption and maximize benefits.
- Executive Support:
- Provide framework for the CEO's technology-related appointments, manage day-to-day technology readiness and lifecycle, with a focus on iOS capabilities.
- Assist in managing the CEO's digital presence, ensuring alignment with organizational branding and strategic objectives.
- Work through ambiguity and shifting priorities, often communicating asynchronously
- Explain technical concepts and recommendations in plain, simple language, with the confidence and clarity that can be acted on immediately.
- Prepare and deliver presentations, reports, and briefings on iOS capabilities and market innovations for the CEO's review and decision-making.
- Support O365 on Mac and Windows workstations for members of the CEO's office and additional SLT members as required.
- Provide on-call technical support for the CEO's office as needed (24x7x365).
- Strategic Planning and Project Management:
- Contribute to strategic technology planning, aligning iOS capabilities and innovations with corporate objectives.
- Lead or participate in cross-functional projects that integrate new market innovations into business processes and workflows.
- Monitor project timelines, budgets, and deliverables, exercising independent judgment when direction is incomplete or evolving.
- Vendor Management and Partnership Development:
- Collaborate with external vendors and technology partners to explore solutions and innovations.
- Manage vendor relationships and oversee service delivery.
Who You Are
- Bachelor's degree in information technology, Computer Science, Business Administration, or related field.
- 5+ years of experience in a technology management role, specializing in iOS, Windows & O365 capabilities and new market innovations in enterprise environments or relevant experience.
- Advanced, native-level fluency in Mac and iOS platforms, with working knowledge of Windows/O365 environments sufficient to bridge the two.
- Demonstrated ability to work through ambiguous or incomplete direction and communicate effectively through intermediaries (executive assistants, chief of staff) rather than direct daily access.
- Exceptional communication skills — able to translate technical complexity into simple, confident guidance for a senior executive audience.
- Unquestionable discretion and judgment in handling highly confidential information.
- Strategic thinking and analytical mindset to evaluate complex technical and business challenges.
Preferred Skills:
- Experience supporting a C-suite executive or high-profile principal directly, including exposure to the confidentiality and pace that role requires.
- Experience with hybrid enterprise environments, including integration of iOS technologies with Windows or Android.
- Familiarity with agile methodologies and rapid prototyping for testing and deploying new innovations.
- Certifications in iOS development, project management, or related fields are a plus.