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 anotherPride: We believe in the importance of our workDynamic: Life is always teaching, so we will continue learning. Integrity: We believe successful relationships require honestyOpen Minded: We are open to new ideas. What You’ll Do: Strategic Planning & Advisory 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 trajectoryBuild and present technology roadmaps that clearly show the ROI and strategic value of IT investmentsLead strategic planning sessions with executive stakeholders to align IT initiatives with business outcomesRun maturity model, security, and stack-alignment assessments to identify gaps and technology risks, then turn findings into prioritized, budgeted recommendationsAdvise clients proactively on infrastructure, cybersecurity, cloud, compliance, and digital transformation, staying ahead of industry trends and emerging technologies (including AI adoption and governance) Client Relationship Management Act as the primary point of contact and trusted advisor for a portfolio of approximately 25 managed services clientsBuild deep, consultative relationships with C-suite executives and key stakeholdersLead quarterly and annual strategic business reviews (QBRs/SBRs) with compelling insights, roadmap updates, and actionable recommendationsHold regular check-ins to keep a pulse on client health, priorities, and satisfactionServe as the escalation point for critical business concerns, partnering with our Service Team to ensure swift resolution and client confidence Client Success & Retention Identify gaps through stack alignment and Lifecycle Manager data, and recommend the right managed services, security, and cloud solutions to close themPartner with Presales and Scoping Engineers to turn roadmap initiatives into scoped solutions and Statement of WorksOwn client health and retention for your portfolio, spotting at-risk accounts early and executing mitigation plans Financial Management & Budget Stewardship Prepare and present clear, accurate IT budgets and technology spend reports to clients and internal leadershipHelp clients negotiate agreements, contracts, and pricing with third-party vendorsMaintain an accurate pipeline of recommendations and statement of works to support forecasting Collaboration & Internal Excellence Work closely with Sales, Service Delivery, Projects, and Support to deliver a seamless client experienceSupport our Professional Services team on client projects, providing business context, keeping clients informed, and helping resolve gapsHelp shape Framework IT’s standard technology stack, vCIO playbooks, SOPs, and thought leadership alongside the Manager of ConsultingMentor junior team members and contribute to the growth of the vCIO practiceKeep timesheets, ConnectWise records, Lifecycle Manager roadmaps, and client documentation accurate and up to date What Success Looks Like: High client satisfaction (CSAT/NPS) and low churn across your portfolioStrong contract renewal rates and client adoption of roadmap recommendationsHealthy account profitability and well-managed, predictable client IT budgetsAccurate, timely reporting and forecasting through your recommendations pipelineLong-term account plans executed with measurable, quantifiable business outcomes for clientsClients who see Framework IT as their trusted advisor and refer us to others What You Bring: 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 preferredExceptional written and verbal communication with executive presence; able to translate complex technical concepts into clear business language and data-driven recommendationsProven track record of building trusted relationships with C-suite stakeholders and leading QBRs or strategic planning sessionsA consultative, advisory mindset, comfortable making and defending recommendations, and working in a KPI-driven environmentSolid understanding of IT infrastructure, networking, cloud platforms (Microsoft 365, Azure, AWS), cybersecurity, and MSP service offeringsWorking knowledge of security and compliance frameworks such as NIST CSF, CIS Controls, ISO 27001, CMMC, and FINRA; experience with cyber insurance requirements a plusExperience with IT budgeting, technology lifecycle planning, and vendor/contract negotiationStrong organizational and time management skills, able to juggle multiple high-priority accounts while working autonomously in a hybrid/remote environmentExperience with ConnectWise PSA and ScalePad Lifecycle Manager strongly preferred (or similar PSA and vCIO/strategy platforms)Bachelor’s degree or equivalent experience Nice to Have: Certifications such as ITIL, CompTIA (Security+, Network+), Microsoft (Azure/M365), CISSP/CISM, or vCIO-specific programsProject management experience or certification (PMP, CAPM)Experience advising clients across a variety of industries, including regulated environments What We Offer: $85,000 to $105,000 starting salary, commensurate with experience and skills Robust medical coverage options plus dental and vision401(k) with partial company matchGenerous PTO and flex time-off policyFlexible hybrid or remote work optionsOccasional client-site visits to support relationship and project needsOngoing training, professional development, and certification/exam reimbursementSupport to attend industry events and conferencesA defined career path; see belowCollaborative, values-driven culture Where This Role Can Take You: This is a career-path role within our Consulting practice. High-performing vCIOs can grow into: Senior vCIO, leading our most strategic client relationships and mentoring the teamLead vCIO, shaping playbooks, standards, and the Framework IT technology stackDirector 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. Powered by JazzHR G2joJo1urF