vCIO - Strategic Technology Advisor

Job Title: Strategic Technology Advisor (Virtual CIO)
Chicago, IL (Hybrid/Remote)  |  Reports to: Director of Operations  |  Full-Time
Framework IT is Chicago’s premier IT Managed Service Provider with a mission of reinventing technology by updating how it is serviced. We base our vision on a ‘client-first’ motto to focus on our clients’ business needs and challenges, then design their support solutions around them.
We believe that investing in the health, happiness, welfare and continued career development of our employees and community allows us to spearhead the next big ideas that will shape the way technology enhances the world around us. Framework IT was founded on the fundamental need to enhance our community and culture through technology. We work together to grow together.
The Role:
Our vCIO Consultant is the trusted executive advisor and strategic owner for a portfolio of Framework IT clients. You’ll sit at the intersection of business and technology, partnering with C-suite leaders to build technology roadmaps, budgets, and security strategies that drive real business outcomes. This is a consultative, relationship-driven role that blends fractional CIO leadership with strategic account management: you’ll own client satisfaction, retention, and the long-term health of roughly 25 client relationships. This is an advisory role, not a sales role; your success is measured by client outcomes and trust, not quota. You won’t just be a vendor contact; you’ll be the person clients call before they make a technology decision.
Who You Are:
Our hiring decisions are based on who you are, not only on what you can do. While skills are important, at Framework we hire the person – not the skillset. We’re looking for someone with our values at their core:

• Teamwork: We work together and for one another.
• Pride: We believe in the importance of our work.
• Dynamic: Life is always teaching, so we will continue learning. 
• Integrity: We believe successful relationships require honesty.
• Open Minded: We are open to new ideas. 
   

• Serve as the strategic partner and advisor for your client portfolio, building long-term account plans aligned to each client’s business goals and growth trajectory.
• Build and present technology roadmaps that clearly show the ROI and strategic value of IT investments.
• Lead strategic planning sessions with executive stakeholders to align IT initiatives with business outcomes.
• Run maturity model, security, and stack-alignment assessments to identify gaps and technology risks, then turn findings into prioritized, budgeted recommendations.
• Advise clients proactively on infrastructure, cybersecurity, cloud, compliance, and digital transformation, staying ahead of industry trends and emerging technologies (including AI adoption and governance).

• Act as the primary point of contact and trusted advisor for a portfolio of approximately 25 managed services clients.
• Build deep, consultative relationships with C-suite executives and key stakeholders.
• Lead quarterly and annual strategic business reviews (QBRs/SBRs) with compelling insights, roadmap updates, and actionable recommendations.
• Hold regular check-ins to keep a pulse on client health, priorities, and satisfaction.
• Serve as the escalation point for critical business concerns, partnering with our Service Team to ensure swift resolution and client confidence.

• Identify gaps through stack alignment and Lifecycle Manager data, and recommend the right managed services, security, and cloud solutions to close them.
• Partner with Presales and Scoping Engineers to turn roadmap initiatives into scoped solutions and Statement of Works.
• Own client health and retention for your portfolio, spotting at-risk accounts early and executing mitigation plans.

• Prepare and present clear, accurate IT budgets and technology spend reports to clients and internal leadership.
• Help clients negotiate agreements, contracts, and pricing with third-party vendors.
• Maintain an accurate pipeline of recommendations and statement of works to support forecasting.

• Work closely with Sales, Service Delivery, Projects, and Support to deliver a seamless client experience.
• Support our Professional Services team on client projects, providing business context, keeping clients informed, and helping resolve gaps.
• Help shape Framework IT’s standard technology stack, vCIO playbooks, SOPs, and thought leadership alongside the Manager of Consulting.
• Mentor junior team members and contribute to the growth of the vCIO practice.
• Keep timesheets, ConnectWise records, Lifecycle Manager roadmaps, and client documentation accurate and up to date.

• High client satisfaction (CSAT/NPS) and low churn across your portfolio.
• Strong contract renewal rates and client adoption of roadmap recommendations.
• Healthy account profitability and well-managed, predictable client IT budgets.
• Accurate, timely reporting and forecasting through your recommendations pipeline.
• Long-term account plans executed with measurable, quantifiable business outcomes for clients.
• Clients who see Framework IT as their trusted advisor and refer us to others.

• 5–7+ years of experience in IT, with at least 3 years in a client-facing vCIO, technical account management, IT consulting, or strategic account management role; MSP experience strongly preferred.
• Exceptional written and verbal communication with executive presence; able to translate complex technical concepts into clear business language and data-driven recommendations.
• Proven track record of building trusted relationships with C-suite stakeholders and leading QBRs or strategic planning sessions.
• A consultative, advisory mindset, comfortable making and defending recommendations, and working in a KPI-driven environment.
• Solid understanding of IT infrastructure, networking, cloud platforms (Microsoft 365, Azure, AWS), cybersecurity, and MSP service offerings.
• Working knowledge of security and compliance frameworks such as NIST CSF, CIS Controls, ISO 27001, CMMC, and FINRA; experience with cyber insurance requirements a plus.
• Experience with IT budgeting, technology lifecycle planning, and vendor/contract negotiation.
• Strong organizational and time management skills, able to juggle multiple high-priority accounts while working autonomously in a hybrid/remote environment.
• Experience with ConnectWise PSA and ScalePad Lifecycle Manager strongly preferred (or similar PSA and vCIO/strategy platforms).
• Bachelor’s degree or equivalent experience.

• Certifications such as ITIL, CompTIA (Security+, Network+), Microsoft (Azure/M365), CISSP/CISM, or vCIO-specific programs.
• Project management experience or certification (PMP, CAPM).
• Experience advising clients across a variety of industries, including regulated environments.

• Robust medical coverage options plus dental and vision
• 401(k) with partial company match
• Generous PTO and flex time-off policy
• Flexible hybrid or remote work options
  • Occasional client-site visits to support relationship and project needs
• Ongoing training, professional development, and certification/exam reimbursement
• Support to attend industry events and conferences
• A defined career path; see below
• Collaborative, values-driven culture

• Senior vCIO, leading our most strategic client relationships and mentoring the team
• Lead vCIO, shaping playbooks, standards, and the Framework IT technology stack
• Director of Consulting and broader leadership roles within Framework IT
  Framework IT is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.