WinkOffice jobs and careers

About WinkOffice

Most companies that struggle with AI don't have a technology problem. They have a leadership problem. No one owns the AI agenda. Teams adopt tools ad hoc. Promising pilots die before reaching production. Money gets spent with no measurable return. WinkOffice fixes that. We embed a senior AI executive into your team. As a leader accountable for outcomes. Strategy, vendor selection, team upskilling, and hands-on execution. From day one. We work with companies between 20 and 500 employees: SaaS platforms adding native AI features, agencies transforming service delivery, engineering teams going AI-native, and mid-market firms that know AI matters but don't know where to start. Two ways to engage: → Advisory Sprint (4 weeks): A deep audit of your tech stack, team capabilities, and AI readiness. Delivered as a concrete, prioritized roadmap. → Fractional Head of AI (ongoing): Embedded leadership 2-3 days per week. We own strategy, build teams, select vendors, ship outcomes, and measure everything. The fractional model means you get senior leadership from day one. No 6-month recruiting cycle, no $400K+ salary, no ramp-up period. Just results. We don't consult. We transform. Book a free intro call → winkoffice.com/book-intro-call