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Virtual Chief Information Officer (vCIO)

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

Virtual Chief Information Officer (vCIO)

Technology Success

La Crosse, Wisconsin office

VP of Service Delivery

Full-Time, Exempt

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

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

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.

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.

• 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.

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 (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:

• 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.

• 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.

• Flexibility with accountability — We trust you to own your schedule and deliver results.
• Values-driven, locally owned MSP — with more than 25 years of industry experience and a strong growth trajectory.
• Meaningful impact — You will work directly with executive clients and see your strategies come to life.
• Collaborative culture — We support each other, celebrate wins, and invest in each other's growth.
• Career development — We invest in your growth and leadership.
• Competitive compensation and comprehensive benefits— including:
  • Health, dental, and vision insurance
  • 401(k) with company match
  • Paid time off
  • Paid holidays
  • Professional development and continuing education support

• Regular travel to client sites throughout Wisconsin, Minnesota, and surrounding service areas is an essential function of this role and may include occasional overnight travel. A valid driver's license, satisfactory driving record, and reliable transportation are required.
• Extended periods of computer and phone use; ability to lead virtual and in-person meetings; ability to travel independently between client sites.
• Occasional lifting of equipment up to 25 lbs.

• Successful completion of a background screening.
• Successful completion of a motor vehicle record (MVR) check.
• Compliance with all company security, confidentiality, and information protection policies.
• Signed offer letter, confidentiality agreement, and IT acceptable use acknowledgment.

Itechra is an Equal Opportunity Employer. We do not discriminate against any employee, applicant, or other covered individual on the basis of race, color, creed, religion, national origin, sex (including pregnancy, childbirth, and related conditions), sexual orientation, gender identity, gender expression, marital status, familial status, status with regard to public assistance, membership or activity in a local human rights commission, disability, age, genetic information, military or veteran status, or any other characteristic protected by federal, state, or local law (including the Minnesota Human Rights Act and the Wisconsin Fair Employment Act). Itechra is committed to providing reasonable accommodations to qualified applicants and employees with disabilities. If you require an accommodation to participate in the application or interview process, please contact Human Resources.