Senior vCIO

Confidential – Senior vCIO / Technical Strategy Lead

Location: San Diego, CA – Hybrid
Compensation: $100,000–$135,000 base + 15% target performance bonus
Benefits: Comprehensive benefits package + 401(k) match

The Opportunity

Our client, a growing San Diego-based Managed Service Provider, is seeking a senior technology professional who can operate at the intersection of IT strategy, technical execution, and emerging AI solutions.

This is not a traditional vCIO role where you simply attend quarterly business reviews and develop technology roadmaps. It is also not a pure engineering position.

The ideal candidate can sit across the table from a business owner in the morning discussing a three-year technology strategy—and later that day roll up their sleeves to design, troubleshoot, or implement the infrastructure required to make that strategy happen.

The role will primarily focus on three areas:

1. vCIO consulting and client technology strategy
2. Technical project engineering and infrastructure delivery
3. Development of the company's emerging AI consulting practice

Approximately 50%–75% of the position will remain technically hands-on, depending on client and project needs.

For someone who enjoys wearing multiple hats, working directly with decision-makers, and having meaningful influence over both clients and the direction of a growing MSP, this is a highly visible opportunity.

What You'll Do

vCIO & Technology Strategy

The most important part of this position is serving as a trusted technology advisor to clients.

You will:

• Develop and maintain technology roadmaps aligned with client business objectives
• Advise business owners and senior executives on infrastructure, security, cloud, productivity, and technology investments
• Lead strategic technology conversations, planning sessions, and client reviews
• Identify technology risks, gaps, lifecycle issues, and opportunities for improvement
• Translate technical challenges into clear business recommendations
• Help clients prioritize technology initiatives based on business impact, risk, budget, and long-term goals
• Build trusted, consultative relationships with multiple client organizations
• Serve as a senior escalation point for complex client technology issues

This role is consultative rather than heavily sales-driven. The goal is to become a trusted advisor who helps clients make better technology decisions.

Technical Engineering & Project Delivery

Unlike many vCIO positions, you will remain actively involved in technical delivery.

You will:

• Design and lead infrastructure projects from planning through implementation
• Participate directly in complex technical implementations and migrations
• Troubleshoot escalated Level 2 and Level 3 infrastructure issues
• Evaluate client environments and recommend architecture improvements
• Lead projects involving servers, networks, cloud platforms, Microsoft environments, security, and related infrastructure
• Coordinate project scope, timelines, resources, and client expectations
• Work independently across multiple client environments
• Partner with internal engineers and technical resources to ensure successful delivery

The successful candidate should still enjoy solving technical problems and be comfortable getting into the details when necessary.

AI Practice Development

The organization is also developing an emerging AI consulting practice and is looking for someone excited about helping shape it.

You will:

• Help evaluate practical AI applications for clients
• Identify opportunities where AI can improve workflows, productivity, and operations
• Participate in developing the company's AI consulting methodology and service offerings
• Help educate clients on AI opportunities, limitations, security considerations, and responsible implementation
• Experiment with and evaluate emerging AI platforms and tools
• Help establish repeatable AI solutions that can eventually be delivered across the client base

The company's current AI efforts are centered around Claude, but the broader goal is to build expertise around practical business applications of AI rather than any single platform.

Previous AI consulting experience is helpful but not required. Curiosity, practical thinking, and a genuine interest in the space are more important.

What We're Looking For

The strongest candidates will bring a combination of strategic consulting ability, technical credibility, and executive-level communication skills.

Required Experience

• Previous experience working within a Managed Service Provider (MSP)
• Strong Level 2–3 systems, infrastructure, or project engineering experience
• Experience advising clients on technology strategy, planning, budgeting, and technology roadmaps
• Demonstrated ability to independently lead infrastructure projects from design through implementation
• Strong client-facing communication and relationship-management skills
• Experience supporting and advising multiple clients and technology environments simultaneously
• Ability to communicate effectively with both technical teams and non-technical executives
• Comfortable remaining technically hands-on while also serving in a strategic advisory capacity

What Will Make Someone Successful Here

We are particularly interested in someone who:

• Thinks like a vCIO first, with a strong understanding of how technology supports business objectives
• Has enough technical depth to earn the respect of engineers and personally execute complex projects
• Can confidently communicate with business owners, CEOs, CFOs, and other senior leaders
• Knows how to simplify complex technical issues and turn them into actionable business recommendations
• Approaches client relationships as a consultant and trusted advisor rather than simply a salesperson
• Enjoys managing different clients, environments, projects, and priorities
• Is excited about helping build an AI consulting capability from the ground up
• Thrives in a smaller, entrepreneurial MSP where responsibilities may extend beyond a narrowly defined job description
• Wants visibility, ownership, and the ability to make an impact

Potential Backgrounds

Candidates may currently hold titles such as:

• vCIO / Virtual CIO
• Senior Systems Engineer
• Senior Project Engineer
• IT Strategy Consultant
• Technical Account Manager
• Solutions Architect
• IT Manager
• Senior Infrastructure Engineer
• Director of Technology within a smaller MSP

Title is less important than having the right combination of MSP experience, strategic consulting ability, and hands-on technical depth.

Location & Work Environment

There is a strong preference for someone located in the San Diego area who values working with colleagues in person and can maintain a regular office presence.

The organization places a meaningful emphasis on culture, collaboration, and relationships, so local candidates will receive preference when qualifications are comparable.

For an exceptional candidate, however, the company may consider a highly hybrid or fully remote arrangement, including candidates located outside California.

Why Consider This Opportunity?

This is an opportunity to move beyond being solely an engineer or solely a strategic advisor.

You will have the ability to:

• Own meaningful client relationships
• Influence technology decisions at the executive level
• Remain technically engaged
• Lead high-impact infrastructure projects
• Help shape an emerging AI consulting practice
• Work directly with company ownership
• Have significant visibility and influence within a growing organization
• Grow with the company as its consulting capabilities continue to evolve

If you are an experienced MSP professional who enjoys strategy, technology, clients, and building something new, this role offers an uncommon combination of all four.

Transition Staffing Group is an award winning San Diego based staffing agency providing solutions on a Temporary, Temporary-to-Hire and Direct Hire basis. Through our affiliate network, we have offices in 35+ metropolitan areas, staffed by over 200 specialized recruiters. TSG offers a national reach, with local job market expertise. Recognized five years in a row by the San Diego Business Journal as one of the "Fastest Growing Privately Held Companies in San Diego." Additionally, recognized on the Inc.500 List twice for being one of the Fastest Growing Companies in the United States. TSG offers full Medical, Dental, Vision, Life Insurance (no waiting period) and matching 401(k) to every active consultant/temp