How we help you
Retailers face complex challenges like changing consumer demands, maintaining profitability, juggling workforce issues and delivering a consistent consumer experience. We provide outsourced C-suite leadership to help you meet those challenges from a strategic perspective.
Get strategic leadership to deliver on organizational goals.
Gain deep experience to complement your internal team.
Scale your outsourced C-suite support according to your needs.
Engage an outsourced executive on a per-project or ongoing basis.
Gain deep industry and operational experience
Our outsourced C-suite team includes retail-specific experience, so we’re not just providing strategic and operational guidance, but a nuanced understanding of the challenges you deal with every day. We also learn about and adapt our efforts to fit how your business functions.
Explore our outsourced c-suite services for retail
Our outsourced chief financial officer services can help your business with:
- Financial analysis
- Strategic planning
- Cash flow forecasting
- Debt structure and refinancing
- Margins evaluation
- Benchmarks and KPIs
- Budgeting and gap analysis
- Spending habits analysis
- Board meeting attendance
- CFO plus training program
Wipfli’s outsourced chief human resources officer can support functions including:
- Compensation and benefits strategy
- Employee experience strategy
- Succession planning
- Leadership development
- Executive coaching
- Organizational structure and role alignment
- Talent strategy and philosophy
- Career pathing
- Talent assessment
Let Wipfli’s outsourced chief information officer assist you with:
- Digital advancements
- IT vendor management
- Performance metrics and benchmarks
- Digital transformation initiatives
- Infrastructure decisions
- IT strategic planning
- IT goal setting
- IT budgeting
- IT process design
Transform how you execute strategy with Wipfli’s outsourced chief operating officer. We can support your business with:
- Strategic planning
- Organizational goal setting
- Metrics and benchmarking analysis
- Annual operational planning
- Planning and organizational functioning
- Vendor management and selection
- Organizational culture enhancement
- Organizational vision
Wipfli’s virtual chief information security officer can help your business with:
- Information security strategy
- Cybersecurity roadmap and reporting
- Cybersecurity compliance
- Security incident response and breach support
- Security architecture and implementation
- Cybersecurity safeguard validation
- Business continuity and disaster recovery preparedness
- Employee security training
- Board and leadership communication
Insights and resources
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Does your business need a fractional chief AI officer?
Within mid-market firms, there’s been much talk about AI as a potential pathway to increased productivity and more effective use of resources. But while many businesses have begun exploring AI tools, one study found that 95% of companies that implemented generative AI pilots said those pilots failed to generate growth . What’s causing this disconnect? Too often, businesses don’t have a real AI strategy to guide where and how they implement AI, which means that AI is often introduced haphazardly and without the focus needed to drive results . What is a fractional chief AI officer? A fractional chief AI officer (CAIO) is an executive-level AI leader who works with an organization on a part-time, interim or flexible basis to help develop and execute its AI strategy. Unlike a full-time chief AI officer, a fractional CAIO provides strategic leadership and hands-on guidance without the cost and long-term commitment of a permanent executive hire. A fractional CAIO helps organizations move beyond AI experimentation by aligning AI initiatives with business goals, identifying high-value use cases, establishing governance frameworks and guiding implementation. The role is especially valuable for organizations that need experienced AI leadership but lack the budget, internal expertise or immediate need for a full-time executive. Roles and responsibilities of a fractional chief AI officer A fractional chief AI officer serves as both a strategic advisor and an execution partner, helping organizations adopt AI responsibly and effectively. Key responsibilities typically include: Developing an AI strategy and roadmap aligned with business objectives, operational priorities and growth goals. Identifying and prioritizing AI use cases that offer the greatest potential for efficiency, innovation and return on investment. Assessing AI readiness across people, processes, data and technology to identify gaps and opportunities. Establishing AI governance and policies to support responsible, secure and compliant AI adoption. Guiding AI implementation and adoption , including technology selection, pilot programs and scaling successful initiatives. Building AI literacy and organizational capability through leadership coaching, employee education and change management. Measuring performance and business impact to ensure AI investments deliver meaningful outcomes and ongoing value. By combining strategic oversight with practical execution support, a fractional chief AI officer helps organizations accelerate AI adoption, reduce risk and create a clear path from AI experimentation to measurable business results. Who needs a fractional chief AI officer A fractional chief AI officer (CAIO) is ideal for organizations that want to capitalize on AI opportunities but do not yet need, or cannot justify, a full-time executive dedicated to AI strategy and governance. This model gives businesses access to experienced AI leadership at a fraction of the cost of a permanent C-suite hire while providing the strategic guidance needed to move from experimentation to measurable business outcomes. Fractional CAIO services are particularly valuable for mid-market organizations, growing companies and mission-driven organizations that need executive-level expertise to develop an AI roadmap, establish governance, prioritize investments and oversee adoption efforts. They can also benefit organizations facing limited internal AI expertise, unclear ownership of AI initiatives or pressure to implement AI without a clear strategy. Several industries can realize significant value from fractional AI leadership: Construction firms can use this to better allow the back office to organize field data and field employees to understand back office financial data. Manufacturing organizations can leverage AI for production optimization, predictive maintenance, supply chain visibility and operational efficiency improvements. Healthcare providers and healthcare-related organizations can benefit from AI-enabled insights, workflow automation, data management and operational modernization initiatives. Higher education institutions can apply AI to student engagement, administrative efficiency, academic support and institutional decision-making. Nonprofit organizations can use AI to strengthen fundraising, donor engagement, reporting, program delivery and resource allocation while maintaining responsible governance practices. Financial services and other data-intensive organizations can benefit from improved analytics, automation, governance and AI-driven decision support. Organizations typically gain the most value from a fractional CAIO when they are ready to move beyond isolated AI experiments and need strategic leadership to align AI investments with business goals, establish responsible governance and create a scalable foundation for long-term success. Comparison of fractional CAIO vs. a full-time CAIO vs. an AI consultant Fractional CAIO Full-time CAIO AI consultant Best fit Organizations that need executive-level AI leadership but do not need a permanent C-suite role. Large or highly complex organizations with enough AI activity to justify a dedicated executive. Organizations that need help with a specific AI project, assessment or implementation need. Business scale Often ideal for mid-market companies, growing businesses and organizations building AI maturity. Best suited for enterprise-scale companies with broad AI teams, multiple business units and ongoing AI transformation needs. Can support businesses of many sizes, especially when the scope is narrow or project-based. Primary focus Aligns AI strategy, governance, use cases and adoption with business goals. Owns enterprise AI strategy, investment decisions, teams, governance and long-term transformation. Provides specialized expertise around a defined AI challenge, technology or implementation project. Engagement model Part-time, interim or flexible leadership role embedded enough to guide strategy and accountability. Permanent executive position with day-to-day ownership of AI strategy and execution. Limited-term advisory or project support, usually tied to specific deliverables. Key advantage Provides strategic AI leadership with more flexibility and lower cost than a full-time executive. Offers continuous leadership and deep organizational accountability for AI transformation. Brings targeted expertise quickly when the business needs support in a specific area. Potential limitation May not be necessary if the organization has very limited AI activity or needs only one narrow technical project. Can be costly and may exceed the needs of organizations still building their AI foundation. May not provide the ongoing executive ownership needed to drive firmwide AI strategy and adoption. When should your business consider hiring a fractional chief AI officer? A fractional chief AI officer can help when your organization is investing in AI but lacks the strategic leadership to turn that investment into measurable business value . Here are signs you may need fractional AI leadership: Low ROI on AI investments: You’ve invested in AI tools, but they aren’t improving performance because they aren’t connected to a clear, organization-wide strategy. Poor-quality AI insights: Your AI-powered analytics produce inconsistent results, potentially because you lack a unified data strategy and reliable, high-quality data. Unfocused AI initiatives: You’re adopting AI to keep pace with competitors rather than identifying specific business problems it can solve. Low employee adoption: Your team is expected to use AI without the skills, training or guidance needed to integrate it effectively into their work. A fractional chief AI officer can help align your technology, data and workforce around a practical AI strategy without the commitment of hiring a full-time executive. Benefits of hiring a fractional chief AI officer For large firms, hiring a full-time CAIO makes sense, as there will be more than enough work to justify adding the position. But many middle-market businesses will find that hiring a fractional CAIO hits a sweet spot from a cost-benefit perspective. Here’s what a fractional CAIO can bring to the table: 1. Strategic leadership The overarching responsibility of a fractional CAIO is to help your business use AI to drive results. From a strategic leadership perspective, a CAIO can set specific goals and create a roadmap to help your business achieve them. Your CAIO can also drill down into specific AI tools that will actually provide value, helping you avoid costly mistakes, and play a major role in communicating your AI goals and creating buy-in within your team. 2. Problem-solving focus AI works best when it’s used to solve specific problems that your organization needs to overcome. A fractional CAIO can help not just identify those problems, but also prescribe which AI tools make the most sense for solving them. This kind of problem and solution focus can help make your AI efforts much more successful. You’ll also have the insight to concentrate your investments on where they will create the largest impact. 3. Governance and collaboration Your AI strategy needs buy-in and collaboration from across your business. Your CAIO can create governance structures like an AI oversight committee to lead AI implementation and raise awareness among stakeholders. Plus, this sort of process will help an outsourced CAIO, who doesn’t work in your business full-time, collaborate more effectively with team members who do and ensure that you integrate AI into your core workflows. 4. Innovation culture AI won’t do much for your business if your team doesn’t embrace it . To really make the most of AI, you need to foster a culture of innovation where your whole team, not just your C-suite, is encouraged to talk about problems and explore new solutions. Your CAIO can help lead this innovation culture by establishing lines of communication, empowering change champions to experiment with AI at lower levels of your organization and identifying specific KPIs to help your team assess AI’s impact on their work. How a fractional CAIO builds an AI roadmap A fractional CAIO helps turn AI ambition into a practical roadmap your organization can execute. Rather than starting with tools, the roadmap begins with business priorities: Where can AI improve efficiency, strengthen decision-making, reduce risk or create new value? From there, the CAIO helps leaders identify the highest-value use cases, assess data and technology readiness, and sequence initiatives so AI investments support measurable goals. A strong fractional AI roadmap typically includes four connected workstreams: AI strategy: Define the business problems AI should solve, prioritize use cases by value and feasibility and align AI investments with growth, margin, productivity and risk-management goals. AI implementation: Move priority use cases from concept to pilot to scale, including tool selection, vendor evaluation, workflow design, integration planning and performance measurement. AI governance: Establish the policies, oversight structures, data controls and decision rights needed to support secure, ethical and compliant AI adoption. AI adoption: Build employee confidence through training, change management, leadership communication and clear guidance on how AI should be used in day-to-day work. By connecting strategy, implementation, governance and adoption, a fractional CAIO helps organizations avoid scattered experimentation and build a disciplined path for scaling AI responsibly. The costs of not having an organization-wide AI strategy In an era of economic uncertainty, mid-market firms often think twice before investing in new hires, even fractional ones. But consider that the expense of onboarding a chief AI officer may be significantly lower than the cost of not filling the position. If you don’t have a firmwide AI strategy led by someone who understands how to implement AI technology inside a business, you’re almost certainly going to waste money on AI solutions that don’t pan out. When you do find the right AI tools, you’ll struggle to use them effectively. And you’ll likely lack the strong data foundation you need to generate high-quality AI outputs. Without an organization-wide AI strategy, businesses may face costs such as: Wasted spend on disconnected AI tools: Without a clear strategy, firms may invest in platforms or pilots that do not solve meaningful business problems or deliver measurable ROI. Lower return on the tools that do work: Even successful AI solutions can fall short if employees do not have the processes, training or leadership guidance needed to use them effectively. Poor-quality AI outputs: AI depends on reliable data. Without a strong data foundation, organizations risk inconsistent insights, inaccurate recommendations and limited trust in AI-enabled decisions. Costly rework and course correction: It is often harder and more expensive to unwind poorly planned AI initiatives than to build the right strategy, governance and implementation roadmap from the start. Change fatigue across the organization: Pushing new AI tools without a clear purpose or roadmap can frustrate teams, slow adoption and make future transformation efforts harder. Leadership hesitation around AI: When early AI efforts disappoint, leaders may become reluctant to make future investments, even when stronger opportunities emerge. In other words, inaction on AI leadership and strategy is expensive. It’s harder and more costly to undo your mistakes around AI than it is to get it right the first time, and you’ll also begin to struggle with change fatigue or leadership hesitation if you continue to push AI tech on your organization without a clear roadmap for doing so. Read more AI checklist: Scaling AI in the mid-market What misaligned data is really costing you Surfing the AI tsunami: Scaling AI in the mid-market
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How a vCIO helps businesses avoid ERP implementation failures
A failed ERP implementation can cost your business time and resources. Can hiring a vCIO to lead the implementation process help you avoid a bad outcome?
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A technology outsourcing guide for financial institutions
Learn how managed IT services and a fractional CIO can deliver the technology infrastructure that financial institutions need to stay competitive in today’s market.
Reach out to our team
Let’s talk about how your retail business can gain access to strategic leadership to help achieve your organizational goals by leaning on outsourced C-suite leaders in finance, technology, HR and operations.
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From technology solutions for multi-location operations to tax and accounting support, Wipfli’s retail advisors are ready to help you stay resilient and competitive.
