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Jobs · Information Technology · Wisconsin

Virtual Chief Information Officer

A Hiring Company · La Crosse, WI · 2 mo ago
On-siteInformation Technology$90k–$110k/yrFull-time

About the role

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.

Responsibilities

Key responsibilities include:

  • 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.

Requirements

Required qualifications include:

  • 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 (ConnectWise 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 qualifications include:

  • 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 healthcare, financial services, manufacturing, or professional services.

Skills

Key competencies include:

  • Strategic Advisor — Translates business needs into technology strategy that delivers measurable outcomes.
  • Executive Communicator — Speaks the language of owners and C-suite leaders as fluently as the language of IT.
  • Relationship Builder — Earns and maintains trust across long-term client engagements.
  • Analytical & Financially Fluent — Builds credible business cases, budgets, and ROI models.
  • Accountable & Organized — Manages a portfolio of clients with discipline, follow-through, and consistency.
  • Collaborative — Partners effectively with Sales, Service, and Project teams to drive client success.

Benefits

Itechra offers a competitive compensation package, including:

  • Annual base salary: $90,000 - $110,000
  • Full benefits package, including health, dental, and vision insurance
  • 401(k) with company match
  • Paid time off and paid holidays
  • Professional development and continuing education support

Pay

The annual base salary for this role is $90,000 - $110,000.

Schedule

This is a full-time, exempt position, with regular travel to client sites throughout Wisconsin, Minnesota, and surrounding service areas. A valid driver's license, satisfactory driving record, and reliable transportation are required.

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