Virtual Chief Information Officer Job Onalaska area,Wisconsin USA,IT/Tech

Virtual Chief Information Officer (vCIO)

La Crosse, Wisconsin
• Full-Time
• Strategic Client Advisory

Position

Virtual Chief Information Officer (vCIO)

Department

Technology Success

Location

La Crosse, Wisconsin office

Reports To

VP of Service Delivery

Employment Type

Full-Time, Exempt

Travel

Regular travel to client sites across WI, MN, and surrounding service areas

Compensation

$90,000 – $110,000 annual base salary, plus full benefits package

About Itechra

Itechra is a Managed IT Services Provider (MSP) headquartered in Winona, Minnesota, with additional offices in Rochester and Roseville, Minnesota, and La Crosse, Eau Claire, and Milwaukee, Wisconsin. Since 2001, we have partnered with organizations across a variety of industries to provide technology support, cybersecurity solutions, cloud services, business consulting, and strategic guidance.

We believe technology should support business growth, improve operational efficiency, and create long-term value for our clients. We pride ourselves on strong client relationships, exceptional service, and operating as a strategic technology partner, not just a vendor.

Position Overview

Itechra is seeking an experienced Virtual Chief Information Officer (vCIO) to join our growing Client Services team, based out of our La Crosse, Wisconsin office. In this role, you will act as a strategic partner to our clients — helping them leverage technology to drive business growth, strengthen security, and align IT initiatives with long-term business goals.

You will work directly with business owners and C-suite leaders across a range of industries, guiding them through IT planning, budget strategy, compliance, and roadmap execution. Internally, you will collaborate with a passionate team dedicated to delivering exceptional IT outcomes.

If you are a tech-savvy relationship builder who thrives on strategic impact and client success, we want to hear from you.

Key Responsibilities

Serve as the trusted strategic advisor to owner and C-suite stakeholders — the person clients call before making significant business or technology decisions.

Build and maintain forward-looking, multi-year technology roadmaps for every assigned client, sequenced by business priority, budget, and risk.

Lead Technology Business Reviews on a defined cadence, keeping every conversation focused on the client's business objectives.

Own each client's technology alignment against Itechra's standards and drive measurable year-over-year improvement.

Translate roadmaps into prioritized, business-justified project recommendations.

Maintain a current view of each client's risk and compliance posture, and ensure the roadmap addresses material gaps.

Partner with Itechra's Sales, Service, and Project teams to ensure client strategy is executed effectively.

Contribute to the ongoing improvement of Itechra's vCIO methodology, tools, and client experience.

Qualifications

Required:

Five (5) or more years in a client-facing strategic/advisory IT role (CIO, vCIO, IT consulting, or senior account/technology management).

Proven ability to lead executive-level (owner / C-suite) conversations and drive decisions.

Track record of building technology roadmaps and converting them into funded, executed projects.

Skill in developing business cases, technology budgets, lifecycle planning, ROI analyses, and total cost of ownership recommendations.

Working knowledge of IT infrastructure, systems, security, and risk — credible with both technical teams and business leaders.

Experience with PSA, CRM, and documentation platforms (Connect Wise Manage, IT Glue, HaloPSA, Salesforce, or equivalent).

Bachelor's degree in Information Technology, Business, or a related field, or equivalent practical experience.

Valid driver's license, satisfactory driving record, and reliable transportation.

Preferred:

Prior experience within a Managed IT Services Provider (MSP) environment.

Familiarity with cybersecurity frameworks (NIST CSF, NIST 800-171, CIS Controls, ISO 27001, CMMC 2.0).

Relevant industry certifications (ITIL, PMP, CISSP, CISM, CompTIA, Microsoft, or vendor-specific).

Experience serving small to mid-sized businesses (SMB) across regulated industries such as…