CIO

Keystone Distinction Group; Pittsburgh (Allegheny County); On-site; USD 180,000 - 320,000; Full time

Job summary

Keystone Distinction Group seeks a forward-thinking Chief Information Officer to lead its technology strategy and digital evolution in Pittsburgh. This is a strategic role, not a maintenance position, with cloud-first operations and an emphasis on AI, cybersecurity, and data-driven decision making.

As a member of the senior leadership team, the CIO will translate technology into measurable business value, build a high-performing team, and partner with executives to drive modernization across the

Qualifications

• 10+ years of progressive leadership experience in information technology.
• Experience developing and executing enterprise technology strategies.
• Knowledge of cloud and SaaS environments.
• Strong understanding of ERP systems and project management methodologies.
• Excellent communication to engage senior executives and Boards.

Responsibilities

• Develop and execute an enterprise-wide technology roadmap aligned with growth objectives.
• Lead AI adoption, automation, and digital transformation initiatives.
• Champion data governance, analytics, reporting, and BI capabilities.
• Oversee cybersecurity governance, risk management, and business continuity.
• Manage vendor relationships, contracts, and strategic technology investments.
• Provide strategic leadership across multiple locations and drive innovation with operational discipline.

Skills

Executive Leadership

Cloud-first

AI & Automation

Cybersecurity

Data Analytics

Vendor Management

Education

Bachelor's degree in Computer Science, Information Technology, Business Administration, or a related discipline

Job description

Chief Information Officer (CIO)

Location: Pittsburgh, PA
Executive Leadership Opportunity

The Opportunity

Our client is seeking a forward-thinking Chief Information Officer (CIO) to lead the next chapter of its technology strategy and digital evolution.

This is not a “keep the lights on” IT leadership role.

The organization has already made significant investments in modernization and operates within a sophisticated, cloud-first technology environment. The next CIO will inherit a strong foundation and have the opportunity to build upon it — using technology, data, automation, AI, and cybersecurity to improve how the organization operates, makes decisions, and grows.

As a key member of the senior leadership team, the CIO will serve as both technology leader and business strategist, partnering closely with executive leadership to identify opportunities, challenge conventional thinking, simplify processes, and ensure technology is delivering measurable business value.

The ideal candidate combines strong technical depth with executive presence, business acumen, curiosity, and the ability to translate emerging technology into practical solutions.

What You’ll Lead

Technology Strategy & Transformation

• Develop and execute an enterprise-wide technology roadmap aligned with the organization’s strategic priorities and long-term growth objectives.
• Identify opportunities to use technology to simplify operations, eliminate inefficiencies, improve productivity, and enhance decision-making.
• Continuously evaluate emerging technologies and determine where they can deliver meaningful business impact.
• Advance a modern, scalable, cloud-first technology environment capable of supporting continued organizational growth.
• Position technology as a competitive advantage and strategic business enabler, rather than simply a support function.
• Balance innovation with operational stability, security, governance, cost, and risk.

AI, Automation & Innovation

• Take a leadership role in the organization’s continued adoption of artificial intelligence and automation.
• Identify practical opportunities to incorporate AI into workflows, business processes, analytics, and employee productivity.
• Establish and evolve responsible AI governance, policies, education, and adoption standards.
• Partner with business leaders to move promising ideas from concept to implementation.
• Stay ahead of emerging technology trends and help leadership understand which developments matter — and which do not.

Data & Business Intelligence

• Champion the use of data as a strategic organizational asset.
• Continue advancing enterprise analytics, reporting, and business intelligence capabilities.
• Improve access to meaningful information across the organization and enable leaders to make faster, more informed decisions.
• Promote strong data governance, integrity, accessibility, and security.

Cybersecurity, Risk & Business Continuity

• Maintain a strong enterprise cybersecurity posture and continually evaluate emerging threats and vulnerabilities.
• Provide executive leadership and the Board with clear visibility into cybersecurity, technology risk, and organizational readiness.
• Ensure effective business continuity, disaster recovery, incident response, and data protection strategies.
• Establish appropriate controls without creating unnecessary barriers to innovation or productivity.
• Ensure technology practices remain aligned with applicable corporate, legal, contractual, and regulatory requirements.

Technology Operations & Partnerships

• Provide executive oversight of enterprise applications, cloud infrastructure, collaboration platforms, integrations, data environments, and technology services.
• Evaluate technology investments based on business impact, scalability, security, usability, and return on investment.
• Lead key vendor and technology partner relationships, including contract negotiation, performance management, and strategic sourcing.
• Ensure major technology initiatives are delivered effectively and achieve their intended business outcomes.
• Develop and manage the technology budget while balancing innovation, security, reliability, and responsible spending.
• This role will provide strategic leadership and oversight for IT operations and support across multiple locations in several states.

Leadership That Makes an Impact

Technology expertise is important, but this role requires much more.

The CIO will be expected to build strong relationships across the organization and create credibility with both technical and non-technical leaders. This individual must be comfortable moving between the boardroom and the operational details of a major technology initiative.

The successful candidate will:

• Build, mentor, and develop a high-performing technology team.
• Create accountability while encouraging innovation and new ideas.
• Communicate complex technology issues in clear, business-oriented language.
• Develop strong partnerships with senior leaders and key stakeholders.
• Bring sound judgment to decisions involving technology, investment, risk, and organizational change.
• Create an environment where the technology function is viewed as a trusted, proactive partner to the business.
• Lead change effectively and help the organization embrace new tools, processes, and ways of working.

What We’re Looking For

We’re seeking an accomplished technology executive who knows how to connect technology strategy with business strategy.

The ideal candidate will bring:

• 10+ years of progressive leadership experience within information technology, including significant senior-level responsibility.
• Demonstrated success developing and executing enterprise technology strategies.
• Knowledge of Vista is highly preferred.
• Strong understanding of modern cloud and SaaS environments.
• Proven ability to collaborate effectively with management teams across multiple locations nationwide, building alignment and ensuring technology initiatives support organizational priorities.
• Comprehensive expertise in enterprise resource planning (ERP) solutions, with strong knowledge of project management methodologies, tools, and systems used to successfully lead complex technology initiatives.
• Strong knowledge of cloud platforms and infrastructure, including Amazon Web Services (AWS) and Microsoft Azure.
• Experience leading technology modernization, digital transformation, or enterprise-wide technology initiatives.
• Strong knowledge of cybersecurity governance, risk management, business continuity, and disaster recovery.
• Experience managing enterprise technology vendors, strategic partners, contracts, and technology investments.
• Exposure to AI strategy, governance, implementation, or enterprise adoption strongly preferred.
• Demonstrated ability to lead and develop high-performing technical teams.
• Exceptional communication and presentation skills with the ability to engage senior executives and Boards of Directors.
• Strong business acumen and the ability to evaluate technology through the lens of organizational value and ROI.
• The position requires regular on-site visits and occasional travel for several consecutive days to ensure consistent operations, effective support, and alignment across all locations
• Bachelor’s degree in Computer Science, Information Technology, Business Administration, or a related discipline.

The Person Behind the Resume

Beyond experience, our client is looking for a leader who is strategic, curious, pragmatic, collaborative, and willing to challenge the status quo.

The right CIO will know when to innovate, when to simplify, when to push forward, and when to protect the organization from unnecessary risk.

Most importantly, this individual will understand that great technology leadership isn’t about technology for technology’s sake.

It’s about making the business smarter, faster, safer, and better positioned for what’s next.