Job Description

We are seeking a visionary and strategically minded Chief Information Officer (CIO) to lead our technology and product strategy. The ideal candidate is a seasoned IT and product executive with deep experience in enterprise infrastructure, software development, end-to-end product lifecycle, and compliance. This role will partner closely with executive leadership to align strategy and business goals with technical execution, while fostering innovation and maintaining a secure, scalable, and high-performing IT environment.

Microsoft-based infrastructure using primarily Windows desktop OS and Windows Server with Office 365; primarily .Net web and desktop development utilizing Microsoft SQL database back-end and limited use of Azure blob storage; integrations with Microsoft’s Dynamics Navision, D365 systems, UPS WorldShip, ShipWise, and Endicia; Palo Alto security network has been implemented; SOC 2 Type 2.

Education and Certifications :

• Bachelor’s degree in Computer Science, Engineering, Information Systems, or related field.
• Masters degree in Business Administration (MBA) or comparable preferred.
• Certifications (Preferred / Bonus) : CISSP, CISM, PMP, or Product Management certifications (e.g. Pragmatic Institute, SAFe, or Scrum.org)

Reporting Structure

This position reports to the CEO.

Key Responsibilities :

Technical Leadership & Strategy

• Define and execute a scalable, secure, and cost-efficient enterprise IT roadmap aligned with organizational goals.
• Lead architecture decisions across cloud infrastructure (Azure), cybersecurity, and DevOps.
• Oversee IT operations, systems reliability, and risk management to ensure 24 / 7 business continuity.
• Champion the adoption of emerging technologies (e.g., AI, blockchain, digital identity) to enhance services and differentiate the business.
• Leverage AI and any emerging technology in an effort to expedite software development cycles while actively reducing and managing overhead expenditures.

Product Development & Delivery

• Serve as the senior most product leader. Own the full product lifecycle – from strategy through execution – and lead cross-functional delivery teams.
• Direct the full product lifecycle from discovery to deployment, focusing on SaaS and user-centered innovation.
• Manage cross-functional teams of developers, database administrators, systems and network administrators and UX / UI designers under Agile / Scrum frameworks.
• Establish and optimize CI / CD pipelines and software delivery best practices.
• Ensure full compliance with privacy laws and data protection regulations (e.g., GDPR, CCPA, FERPA, HIPAA).
• Oversee and enhance the organization’s NOC / SOC operations, including disaster recovery planning, tiered support escalation, and on-call rotation strategies, with a focus on maximizing system uptime, ensuring rapid incident response, and maintaining business continuity across all critical infrastructure.
• Lead and manage certification processes such as SOC 2, ISO 27001, or NIST, including audits, documentation, and policy implementation.
• Advise on secure identity, e-Notary, and digital signature technologies as applicable to product and operational domains.

Cross-Functional Collaboration & Leadership

• Serve as the primary technology advisor to the CEO and executive team, providing insights that bridge business strategy and technical execution.
• Foster collaboration across departments, including legal, operations, finance, marketing, and sales.
• Develop and mentor high-performing leadership across IT and product functions.

Ideal Background & Experience :

Technical Leadership

• 10–15 years of progressive IT experience, with a minimum of 5 years in a senior leadership capacity (CIO, CTO, VP of IT / Product).
• Deep expertise in enterprise architecture, cloud platforms (AWS, Azure), cybersecurity, and modern DevOps practices.

Product Development

• Demonstrated success in launching and scaling software products, while supporting the technical environment, ideally in a SaaS environment.
• Proficient in Agile methodologies, design thinking, and iterative delivery models.

Compliance & Risk

• In-depth knowledge of U.S. and international data privacy regulations (GDPR, CCPA, FERPA, HIPAA).
• Hands-on experience managing compliance programs, audits, and related documentation.
• Familiarity with secure authentication systems, e-signatures, and identity frameworks is highly desirable.

Soft Skills

• Strong executive presence with excellent verbal and written communication skills.
• Proven ability to influence across departments and build consensus at the executive level.
• Strategic thinker with the foresight to identify and harness emerging tech trends.

Physical Requirements :

• This is primarily an office-based job that may require sitting for extended periods of time working on a computer.
• Onsite at our offices in Virginia Beach, VA.
• Ability to travel based on company needs.
• Valid driver’s license required.
• Good vision, with or without corrective lenses, to sustain adequate visual focus over a period of time.
• Fine motor skills, including, but not limited to, the full, complete use of and muscle control required to make precise hand movements, relative to tasks requiring hand-eye coordination, muscle coordination and dexterity.

Compensation and Benefits

• Full-Time salaried, exempt position with on call availability for emergencies
• Medical, dental and vision insurance
• 401K with company matching
• Paid sick- and annual-leave
• Paid holidays

Additional Information and Signature

For over 34 years, Paradigm, Inc. has proven to be a unique, successful, and dynamic company with a reputation of being best-in-class. A positive attitude, proven work ethic and a consistent capacity to learn and surpass expectations are what you will find in our leadership and employees. We seek diligent and curious individuals who possess a proven record of interpersonal people skills, cultural integrity, and the required skills to join our team.

Simply stated, we want you to be successful : we therefore make every effort to quantify a candidate’s suitability before an offer of employment is extended. Hence, interviewing at Paradigm is a multi-stage process. Included in our evaluations are at least two site visits, question and answer panels, skill, and various personality and work-style assessments.

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