First 90 Days with a Fractional CAIO: Your Timeline

You’ve decided to bring on a Fractional Chief AI Officer. What happens next? What should you expect in the first weeks and months? How quickly will you see results?

This article walks through a typical 90-day timeline for a Fractional CAIO engagement, so that you know what to expect, how to prepare, and most importantly, how to measure whether things are on track.

Of course, every engagement varies based on company size, complexity, and specific objectives. Still, this timeline offers a realistic view of how the first three months typically unfold—and as a result, what “good progress” looks like at each stage.

Before Day One: Preparation

The engagement starts well before the official kickoff. In fact, during the contracting and onboarding period, you’ll complete a few preparation steps that ultimately accelerate time to value.

Define your objectives clearly. What do you want to achieve with AI? Cost savings? Revenue growth? Competitive positioning? The clearer your goals, the more focused the engagement.

Identify key stakeholders. Who needs to be involved in AI initiatives? Who will the CAIO work with most closely? Prepare these people for the engagement.

Gather relevant documentation. The CAIO will want to understand your business, including organizational charts, process documentation, technology inventory, strategic plans, and financial information. Having this ready saves time.

Prepare system access. The CAIO may need access to your CRM, scheduling system, marketing platforms, and other tools. Coordinate with IT to have accounts ready.

Schedule initial meetings. Block time on calendars for the kickoff meeting and initial stakeholder interviews. Protecting this time ensures the engagement starts strong.

Days 1-14: Discovery and Assessment

The first two weeks focus on understanding your business, current state, and opportunities.

The kickoff meeting aligns everyone on objectives, process, and expectations. This typically includes executive sponsors and key stakeholders. The CAIO outlines their approach and gathers initial context.

Stakeholder interviews follow over the first two weeks. The CAIO meets with department heads and key employees to understand operations, pain points, and perspectives on AI opportunities. These conversations surface insights that don’t appear in documentation.

Process observation lets the CAIO see how work actually happens. They may shadow customer service calls, observe scheduling workflows, or watch how estimates are prepared. This firsthand observation reveals automation opportunities.

Technology audit reviews your current systems—what tools you use, how they’re configured, how well they integrate, and where gaps exist. This informs what AI solutions can build on existing infrastructure.

Data assessment examines what data you have, its quality, accessibility, and potential value. Data is fuel for AI, and understanding your data assets shapes strategy.

By the end of week two, the CAIO has a comprehensive understanding of your business and initial hypotheses about where AI can create the most value.

Days 15-30: Strategy and Roadmap Development

Weeks three and four synthesize discovery findings into actionable strategy.

Opportunity identification documents specific AI use cases with estimated impact, implementation complexity, and dependencies. This analysis typically surfaces 10-20 potential initiatives.

Prioritization frameworks help select which opportunities to pursue first. Common criteria include ROI potential, implementation complexity, organizational readiness, and strategic alignment. The CAIO facilitates this prioritization with leadership.

The AI roadmap sequences prioritized initiatives over the coming 6-18 months. It defines what gets done when, what resources are required, and what dependencies exist between initiatives.

Governance framework development establishes policies for AI use—what’s allowed, what requires approval, how quality is assured, how data is protected. This framework enables responsible AI adoption.

Success metrics define how you’ll measure AI initiative success. Metrics might include hours saved, revenue influenced, adoption rates, or customer satisfaction improvements.

The strategy presentation shares findings and recommendations with leadership. This session aligns everyone on the path forward and secures commitment to proceed.

Deliverable: By day 30, you have a documented AI strategy and roadmap, typically presented in a strategy document and executive presentation.

Days 31-60: Quick Win Implementation

The second month focuses on early implementations that deliver visible value.

Quick win selection chooses 1-3 initiatives from the roadmap that offer good ROI with manageable complexity. These might include customer communication automation, AI-assisted content creation, or review management optimization.

Tool selection and procurement identifies the specific AI tools needed for quick wins. The CAIO evaluates options, makes recommendations, and helps negotiate with vendors if needed.

Implementation begins with the CAIO overseeing setup, configuration, and integration of selected tools. Depending on the engagement scope, they may do hands-on configuration or guide your team through the process.

Team training ensures the people who will use AI tools understand how to use them effectively. Training covers both tool mechanics and judgment about when and how to apply AI assistance.

Process integration embeds AI tools into real workflows. In practice, this usually means adjusting existing processes so AI assistance fits naturally—for example, clarifying when AI is used, who reviews outputs, and how work moves through the updated workflow.

Early results tracking monitors initial performance to confirm the implementation is working and identify any needed adjustments.

By day 60, you should have at least one AI initiative live and delivering measurable value. This creates momentum and demonstrates the engagement’s worth.

Days 61-90: Expansion and Optimization

The third month expands on early success while refining what’s been implemented.

Quick win optimization improves initial implementations based on real-world experience. Prompt refinements, workflow adjustments, and additional training address any gaps or issues that emerged.

Adoption monitoring tracks how well team members are actually using new AI tools. The CAIO identifies adoption barriers and addresses them through additional training, process changes, or tool adjustments.

Secondary initiative launch begins implementing the next priority from the roadmap. With quick wins established, the organization is better prepared for more complex initiatives.

Knowledge transfer ensures your team can maintain and optimize AI implementations without constant CAIO involvement. Documentation, training, and internal champion development build sustainable capabilities.

Stakeholder communication keeps the organization informed about AI progress. Success stories, metrics, and roadmap updates maintain engagement and support for ongoing initiatives.

90-day review assesses what’s been accomplished, what’s worked well, what needs adjustment, and what comes next. This review typically results in a refined roadmap and recommendations for the ongoing engagement.

What Success Looks Like at 90 Days

By the end of the first 90 days, a successful engagement should have achieved several concrete outcomes.

Clear AI strategy exists. You have a documented roadmap showing where AI will be applied, in what sequence, and with what expected outcomes.

Governance is in place. Policies and guidelines establish how AI is used responsibly across the organization.

At least one initiative is live. In other words, you’re not just planning—you already have AI working in the business and delivering measurable value.

Team capability has increased as well. As a result, people across the organization understand AI’s role, and at least a few staff members can use the tools effectively in day-to-day work.

Momentum is building. Success breeds success. Early wins create enthusiasm and support for continued AI investment.

Leadership is aligned. Executives understand the AI opportunity, have confidence in the approach, and are committed to ongoing investment.

Not everything will be perfect. Some initiatives may need refinement. Some adoption barriers may persist. But the foundation is set for continued progress.

Setting Yourself Up for Success

Several factors influence how successful the first 90 days will be. You can control many of them.

Executive sponsorship matters enormously. When senior leaders visibly support AI initiatives, signal their importance, and hold people accountable for adoption, progress accelerates.

Resource availability affects pace, too. If key people are too busy to participate in interviews, training, or implementation, the engagement slows down. To avoid that, protect time for AI initiatives.

Decision-making speed also shapes what’s possible in 90 days. If every tool purchase or process change requires extended approval cycles, fewer initiatives can launch. For that reason, establish decision authority upfront.

Realistic expectations help everyone stay grounded. AI transformation is a journey, not a sprint. The first 90 days build foundations; full value realization takes longer.

Open communication between you and the CAIO ensures issues surface quickly and get resolved. Share feedback, ask questions, and voice concerns as they arise.

Commitment to change separates companies that successfully adopt AI from those that struggle. AI implementation requires changing how people work. Organizations resistant to change will struggle regardless of strategy quality.

A Fractional Chief AI Officer brings expertise and frameworks, but your organization’s engagement determines how effectively that expertise translates into results.

Beyond 90 Days

The first 90 days establish foundations, but AI transformation continues well beyond this initial period.

Ongoing optimization improves initial implementations, captures more value from deployed tools, and addresses edge cases and exceptions.

Roadmap execution implements additional initiatives from the prioritized roadmap, building on capabilities established in the first 90 days.

Continuous learning keeps your AI capabilities current as tools evolve, new capabilities emerge, and best practices develop.

Organizational development builds internal AI expertise, develops champions across departments, and creates sustainable AI capability that doesn’t depend entirely on the CAIO.

Strategic evolution updates your AI strategy as business needs change, market conditions shift, and new opportunities emerge.

The relationship with your Fractional CAIO may evolve over time—intensifying during major initiatives, lightening during steady-state periods, and adapting as your needs change. The first 90 days set the trajectory for this ongoing partnership.

Ready to Bring AI Leadership to Your Business?

The FS Agency provides Fractional Chief AI Officer services for mid-sized businesses ready to implement AI strategically. Our tiered engagement packages start at $5,000 per month.

Contact us: fsagency.co/ai-consulting | 303-578-8299