FAQ

Frequently asked questions

Everything you need to know about fractional AI leadership and working with WinkOffice.

About WinkOffice

What does a Fractional Head of AI do?
A Fractional Head of AI is an embedded executive who owns your AI strategy, adoption, and engineering direction — part-time, without the cost or commitment of a full-time hire. They lead your AI transformation the way a CTO leads engineering: setting direction, building teams, selecting vendors, and shipping outcomes.
How is this different from an AI consulting firm?
Consultants deliver reports and recommendations. We deliver results. A Fractional Head of AI joins your team, attends your standups, leads your people, and is accountable for outcomes — not slide decks. We're embedded, not external.
What size companies do you work with?
We work best with companies between 20 and 500 employees — large enough to benefit from structured AI leadership, lean enough to move fast. This includes SaaS companies adding native AI features, agencies transforming their service delivery, and mid-market firms beginning their AI-native journey.

Working Together

What does the engagement process look like?
It starts with a free 30-minute intro call to understand your situation. From there, we typically begin with a 4-week Advisory Sprint — a deep audit of your tech stack, team capabilities, and AI readiness. This produces a concrete roadmap. If there's a fit for ongoing leadership, we transition into the Fractional Head of AI engagement.
How long does a typical engagement last?
The Advisory Sprint is 4 weeks. Fractional Head of AI engagements typically run 6 to 12 months, depending on the scope of transformation. Some companies keep us on longer-term for continuous optimization. There are no lock-in contracts.
Can you work with our existing tech team?
Absolutely — that's the point. We lead and upskill your existing team rather than replacing them. The goal is to make your organization AI-native, not dependent on external resources. We work alongside your engineers, product managers, and leadership.

AI Transformation

What does "AI-native" mean?
AI-native means AI is woven into how your company operates — not bolted on as an afterthought. It's the difference between giving everyone ChatGPT access and fundamentally redesigning workflows, products, and decision-making around AI capabilities. It requires leadership, not just tools.
How do you measure AI ROI?
We set measurable KPIs from day one: engineering velocity improvements, cost reduction in AI tooling spend, time-to-production for AI initiatives, and team adoption rates. Every engagement starts with a baseline assessment so we can quantify the impact.
What's the difference between AI tools and AI transformation?
AI tools solve individual problems — a chatbot here, an automation there. AI transformation changes how your entire organization thinks, builds, and delivers. Tools are tactics. Transformation is strategy. Without leadership, tool adoption becomes fragmented shadow AI.

Pricing & Logistics

How much does a Fractional Head of AI cost?
Pricing depends on scope, time commitment, and the complexity of your AI landscape. It's a fraction of what you'd pay for a full-time VP of AI (typically $300K-$500K+ total comp), and you get senior leadership from day one — no recruiting cycle, no ramp-up period. Book a free intro call and we'll give you a transparent quote.
Do you offer a trial period?
The 4-week Advisory Sprint is effectively a trial. It gives you a concrete AI roadmap and lets both sides evaluate the fit before committing to an ongoing engagement. There's no obligation to continue beyond the sprint.
What happens after the Advisory Sprint?
You receive a detailed AI readiness report, a prioritized roadmap, and clear KPIs. From there, you can execute independently, bring us on as Fractional Head of AI for ongoing leadership, or revisit later. The roadmap is yours regardless.

Still have questions?

Book a Free Intro Call