1. How long have you been a vCIO and what are your experiences and credentials?

I’ve held the vCIO (Virtual Chief Information Officer) title for six years now. However, in my 30+ years in the IT field, I been in a business advisory role for all my clients. This includes when I was the Director of IT for a 13-office dental practice, worked for other managed service providers, or even when I owned my own IT company.

2. What is a vCIO and why do law firms need them?

A vCIO is a strategic IT business advisor. I focus on your goals, profits, and business outcomes. vCIOs help organizations - especially small to mid-sized businesses, often times which include law firms - align technology initiatives with business objectives and goals, ensure IT governance, help manage risk, remove surprises from their road map, and plan for future growth. Law firms have specific nuances based on their area of practice and firm size that have to be considered. This is where a vCIO and a team that truly understands those challenges can be a game changer for a firm.

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3. What is the difference between a vCIO and an in-house CIO?

A vCIO is an outsourced advisor who provides strategic IT leadership to multiple clients, typically as part of an MSP’s offerings. A traditional CIO is a full-time employee dedicated exclusively to a single organization. The vCIO offers flexibility and cost efficiency and may offer a greater pool of knowledge as he’s not a single resource and is often backed by a brain trust consisting of highly skilled engineers.

Law firms use vCIO services to gain strategic guidance and oversight of their technology. We help address modern challenges like AI security (aka data governance), client compliance demands, cloud adoption, and aligning technology with the firm’s growth and goals.

5. How does working with a vCIO make life easier for law firms?

Working with a vCIO makes life easier for law firms by simplifying technology decisions, reducing risk, and ensuring systems support the way attorneys work. They provide clear IT roadmaps, manage vendor relationships, and proactively handle compliance and security, freeing up firm leadership to focus on clients, cases, and profits.

6. Not all IT clients require large changes and overhauls, but sometimes, things change. When it becomes necessary, how do you help law firms address large-scale changes?

When large-scale changes become necessary, we help law firms navigate them with minimal disruption by providing a clear, strategic framework. This includes assessing the current environment, identifying risks and readiness gaps, and building a phased roadmap that aligns with the firm’s operational cadence, budget, and compliance needs.

Whether it's a cloud migration, security overhaul, or digital transformation initiative, the vCIO coordinates with legal and non-legal vendors and internal stakeholders to ensure seamless execution. We help set and manage expectations, and provide executive oversight, ensuring that priorities stay aligned, risks are mitigated, and the impact to the firm is kept minimal.

7. What about the day-to-day? How does a vCIO help keep law firms running smoothly over time?

A vCIO helps keep law firms running smoothly by aligning technology with the firm’s workflow, setting the stage for long-term scalability, advising on their security posture, and keeping up with compliance requirements. We proactively guide strategic planning by evaluating systems for improvement, coordinating with service providers, and advising on when to adopt or retire technology. Over time, we help firms avoid costly missteps, ensure that IT investments support attorney productivity, and ensure understanding and adherence to cybersecurity measures.

We began with a targeted alignment review and security assessment, then built a phased roadmap that addressed immediate gaps without overwhelming the firm or disrupting casework. Over the next 12 months, we consolidated their tech stack, migrated them to a more secure cloud-based document system, implemented MFA firm-wide, and helped them pass a rigorous client audit.

What stuck with me wasn’t just the technical progress; it was seeing how a strategic partnership and measured guidance helped position the firm as a more competitive, client-ready practice.

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9. vCIOs help law firms address a rapidly changing future and achieve business goals and an overall vision through IT strategy. What does the process of building that strategy look like?

There are several different components that go into this phased approach. For example:

Discovery & Stakeholder Engagement:
Discussions with firm leadership, attorneys, and key staff to understand business objectives, pain points, compliance obligations, and client expectations.

Current State Assessment:
Next, we conduct a thorough review of the firm’s existing technology stack, infrastructure, security posture, and vendor relationships. This assessment identifies risks, redundancies, underutilized tools, and areas where the current systems do, or don’t, support the firm’s goals.

Alignment Mapping:
We then map existing technology and processes to the firm's operational needs, highlighting where gaps exist. This includes standardization across locations, integration between systems, and support for hybrid/remote workflows.

Roadmap Development:
Using insights from the discovery and alignment phases, we create a multi-phase roadmap that includes:

• Short-term tactical fixes. For example, MFA, backup solutions, onboarding/offboarding processes
• Medium-term modernization plans. So, think security initiatives, disaster recovery planning
• Long-term strategic initiatives. This could include a DMS, AI solutions, or an infrastructure alignment plan

Ongoing Refinement:
Because nothing is more constant than change, we continue to assess client needs, legal regulations, and how technologies evolve. We revisit, review, discuss, and update the strategy, keeping the firm agile, secure, and strategically positioned for long-term success.

10. Law firms have particular and unique security concerns. How does a vCIO keep them safer amidst rising and changing threats?

A vCIO helps keep law firms safer by taking a proactive, legal-specific approach to cybersecurity that goes beyond basic protections. This starts by conducting risk assessments during the onboarding process, then recommending specific tooling that identifies vulnerabilities, accounts for workflows, and manages vendor relationships.

It’s also important that we ensure the firm is meeting rising client and insurance-driven security demands. We do this by deploying adaptive detection tools, reviewing cyber liability coverage requirements prior to renewals, and providing end-user awareness training and reviewing those reports. Aligning cybersecurity with business operations helps firms avoid downtime, prevent data loss, and maintain client trust, all while educating, but not inundating, leadership on evolving risks like ransomware, phishing, and supply chain attacks.

11. How does a vCIO fit into the larger, long-term business strategy of small and mid-sized law firms?

By serving as a strategic partner who aligns technology with the firm’s vision for growth, efficiency, and competitiveness. Rather than focusing solely on IT operations, the vCIO helps define how technology supports broader goals, whether that’s M&A planning, attracting higher-value clients, relocating, or improving compliance.

Over time, the vCIO ensures that technology investments directly contribute to improved service delivery, operational agility, and long-term profitability, positioning the firm to adapt confidently to an increasingly digital legal landscape.

Strategic Roadmap Development: Using our assessment insights, we create a tailored IT roadmap that balances short-term fixes with long-term initiatives, ensuring your technology evolves in step with your firm’s needs.

Ongoing Strategic Oversight: Through regularly scheduled conversations and ongoing strategy sessions, we track progress, adapt to new challenges, and ensure leadership has full visibility into IT priorities and performance.

Collaboration with Internal & External Teams: We partner with your internal staff and vendors to ensure initiatives stay on track, systems remain aligned, and strategic goals are never lost in the day-to-day.

Long-Term Partnership: We continuously monitor the evolving legal tech landscape, compliance standards, and cyber threats to keep your firm ahead and turn IT into a competitive advantage.

13. What kind of time or resource commitment should a law firm expect when engaging with a vCIO?

Initially, in the first 30 - 60 days: 3 – 6 hours. This includes leadership, admin, and support staff.

Ongoing: An hour or so per month for strategic check-ins. This may vary based on initiatives in motion. All meetings are front-loaded with leadership-specific agenda items to ensure the most relevant data is shared and discussed early. This allows leadership to get what they need, and we can wrap up the call with the admin staff.

Engaging a vCIO through a managed service provider offers the firm stability, accountability, and a deeper bench of expertise compared to hiring an individual consultant.

For example:

• Trust & Accountability
• Broader Expertise
• Legal Industry Experience
• Scalability & Continuity
• Strategic Integration with Services

In short, a technology business partner offers not just a person, but an ecosystem, giving your firm greater confidence, continuity, and strategic reach.

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Find the strategic partnership your law firm needs through vCIO services with STS.

vCIO Kasey Wince and the rest of the STS team are here to help law firms reach their strategic goals through our dynamic approach, which includes:  

• Discovering and understanding your law firm’s business needs and goals
• Continually performing in-depth IT assessments to identify gaps and vulnerabilities
• Making IT recommendations and set priorities via a technology roadmap
• Aligning IT initiatives with overall business strategy to provide predictive budgeting to leadership
• Ongoing vendor management to streamline IT operations and increase operational efficiencies and health
• Provide regular reports on network health, systems, usage, support statistics, and other IT performance metrics in easy-to-understand terms.
  

Law firms increase the value of their IT investments through our strategic vCIO Advisory services and the years of experience we bring to the table. STS makes IT projects, aligning technology to business goals, and leveraging your tech stack easier than ever with our expert partnership and locked-arms approach.  

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