Technology Assistant to the CEO

The Gap•Folsom, CA

About The Position

The Technology Assistant to the CEO supports the CEO with advanced technology solutions, with a focus on iOS capabilities and emerging market innovations. The role requires native fluency in the Apple ecosystem, independent judgment amid ambiguous and changing priorities, clear communication of technical concepts, and discretion when handling highly confidential information. It also involves integrating AI solutions into the CEO’s daily workflow to reduce friction and save time. The position manages and optimizes the CEO’s iOS devices, applications, and ecosystem; supports interoperability with enterprise Windows and O365 environments; and provides technical support and troubleshooting. It researches, evaluates, pilots, and implements emerging technologies and AI tools, and contributes to strategic planning and cross-functional projects. The role also provides executive technology readiness, digital presence support, presentations and briefings, O365 support for relevant staff, vendor relationship management, and on-call technical support for the CEO’s office as needed (24x7x365).

Requirements

Bachelor’s degree in information technology, Computer Science, Business Administration, or a related field.
At least 5 years of experience in a technology management role specializing in iOS, Windows and O365 capabilities, and new market innovations in enterprise environments, or relevant experience.
Advanced, native-level fluency in Mac and iOS platforms.
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 rather than having direct daily access.
Exceptional communication skills, including the ability 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 an analytical mindset for evaluating complex technical and business challenges.

Nice To Haves

Experience directly supporting a C-suite executive or high-profile principal, including familiarity with the confidentiality and pace required.
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 innovations.
Certifications in iOS development, project management, or related fields.

Responsibilities

Support, manage, and optimize the CEO’s iOS devices, applications, and ecosystem, including Mac tools such as Mail, Contacts, and Calendar.
Ensure seamless functionality and integration across Macs, iPads, and iPhones, including interoperability with enterprise Windows and O365 environments.
Provide technical support and troubleshooting, resolving issues swiftly and with minimal disruption to the CEO’s day.
Research and evaluate emerging technologies, AI tools, and market trends relevant to the CEO office’s strategic goals.
Identify opportunities to use software, technologies, and AI solutions to improve productivity, efficiency, and competitive advantage.
Pilot and implement innovative solutions, collaborating with internal teams and stakeholders to support adoption and maximize benefits.
Provide a framework for the CEO’s technology-related appointments and manage day-to-day technology readiness and lifecycle, focusing on iOS capabilities.
Assist in managing the CEO’s digital presence in alignment with organizational branding and strategic objectives.
Work through ambiguity and shifting priorities, including communicating asynchronously and through intermediaries.
Explain technical concepts and recommendations in simple, actionable language.
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).
Contribute to strategic technology planning, aligning iOS capabilities and innovations with corporate objectives.
Lead or participate in cross-functional projects integrating new market innovations into business processes and workflows.
Monitor project timelines, budgets, and deliverables, exercising independent judgment when direction is incomplete or evolving.
Collaborate with external vendors and technology partners to explore solutions and innovations.
Manage vendor relationships and oversee service delivery.