Virtual Chief Information Officer in Abington, Pennsylvania at Proper Sky Inc.

Why Work for Proper Sky?

At Proper Sky, your work will make an impact from day one. As a small and agile team, we offer meaningful responsibility early on and continuous opportunities to grow, no matter your role. Every day brings fresh challenges and the chance to build new skills in a collaborative, fast-paced environment.

You’ll work closely with leadership and key stakeholders, gaining visibility and influence across the organization. Our team is made up of dedicated, mission-driven professionals who care deeply about delivering exceptional results for our clients and supporting one another.

We’re committed to your development and success. We provide leadership and professional growth opportunities through industry-leading programs like IT Nation, along with other third-party training and support. At Proper Sky, you’ll learn our systems, improve them, and bring value every day.

About the role

The Virtual Chief Information Officer (vCIO) serves as the strategic technology advisor and executive partner to Proper Sky clients. This role owns the client-facing transformation process, translating business objectives into actionable technology strategies that reduce risk, improve operational maturity, and drive measurable outcomes. The vCIO operates with a seat at the table, leading C-level conversations and providing clear, forward-looking guidance on how technology investments align to each client’s strategic goals. This role partners closely with the Account Management Team, Alignment Team, Support Team, and Professional Services Teams to ensure that strategy is executable, measurable, and consistently delivered.

What you'll do

Strategic Advisory & Client Leadership:

Lead executive-level technology conversations with client stakeholders, including C-suite and senior leadership Translate client business objectives into structured, actionable technology strategies and multi-year roadmaps Provide ongoing technical thought leadership on emerging technologies, cybersecurity, compliance, and operational maturity Establish and maintain a strong understanding of each client’s business model, risks, constraints, and growth initiatives

Technology Roadmap Ownership:

Own the development, maintenance, and execution oversight of client technology roadmaps Ensure roadmaps are prioritized based on business impact and risk reduction Ensure roadmaps are financially aligned with client budgets and planning cycles Ensure roadmaps are structured for execution by internal teams Continuously refine roadmaps based on changing client needs, risks, and business direction

Risk Management & Governance:

Identify, assess, and communicate technical, operational, and cybersecurity risks with internal teams and strategic partners Provide clear remediation strategies with defined timelines and business impact Ensure clients have visibility into current risk posture Ensure clients understand progress toward remediation Ensure clients understand residual risk and trade-offs Drive accountability across internal teams to ensure risk-related initiatives are executed

Quarterly Business Reviews (QBRs) & Client Governance:

Own and lead all QBRs, ensuring they are structured, data-driven, and executive-relevant Present progress against strategic initiatives and roadmap execution Present risk posture and remediation progress Present service performance trends and key metrics Present alignment to business goals and upcoming priorities Present budget alignment and forward planning Ensure QBRs clearly communicate where the client is today, what has improved, what risks remain, and what actions are required next Facilitate occasional monthly governance touchpoints for high-complexity or high-priority clients

Cross-Functional Alignment:

Collaborate with the Alignment Team to ensure standards, configurations, and environments support the roadmap Work with the Support Team to identify trends, recurring issues, and opportunities for improvement Coordinate with the Professional Services Team to ensure successful execution of roadmap initiatives Engage the Finance Team to align budgeting, forecasting, and investment planning with client strategy

Qualifications

Education & Experience:

7+ years in IT leadership, consulting, or advisory roles within an MSP or similar environment Proven experience leading C-level and executive client conversations Strong technical foundation across infrastructure, cloud platforms, cybersecurity, and modern workplace technologies Demonstrated experience building and managing technology roadmaps and strategic plans Experience in risk identification, communication, and remediation planning Ability to translate complex technical concepts into clear business language Experience serving clients in Healthcare, Manufacturing, and/or Non-Profit industries is preferred. Familiarity with compliance and regulatory frameworks such as HIPAA and cybersecurity frameworks,, is preferred Experience operating within or alongside MSP service delivery models

Soft Skills:

Strong problem-solving and analytical thinking skills. Excellent written and verbal communication abilities. Ability to translate business needs into technical requirements. Highly organized, detail-oriented, and documentation-focused. Self-starter with a passion for continuous learning and process improvement. Collaborative mindset with the ability to work across multiple teams and priorities.