Please note that the search for this position is being led by Shira Werblowsky at SW Recruiting. Please direct all inquiries to shira@shirawerblowsky.com
Location / Work Environment:
Hybrid / New York-based / Travel expectations
Position Summary:
The Chief Digital & Innovation Officer (CDIO) is a senior executive responsible for leading the Orthodox Union’s next phase of technology evolution, with a focus on digital transformation, data, artificial intelligence, and enterprise innovation.
This role serves as the senior technology leader, with the Chief Information Officer (CIO) and the IT function reporting into this position. The CDIO partners closely with the CIO, who retains responsibility for day-to-day IT operations, service delivery, and execution.
The CDIO is accountable for defining and driving the organization’s future-state technology vision, aligning technology with enterprise strategy, and leading the transformation of technology capabilities to support scale, efficiency, and innovation.
Core Mandate:
- Define and lead the transformation of the OU’s technology function to a modern, scalable operating model
- Drive adoption of data, AI, and digital capabilities across the organization
- Elevate technology from a support function to a strategic enabler of organizational outcomes
Success in this role will be measured by the degree to which the technology organization is transformed over a 12–24 month period, rather than by day-to-day operational performance.
Organizational Structure:
Reports to: Chief Operations Officer
Direct Reports: Chief Information Officer (CIO) and broader IT leadership
Chief Digital & Innovation Officer (CDIO)
- Owns digital strategy, transformation, and future-state technology direction
- Accountable for enterprise technology outcomes and modernization
Chief Information Officer (CIO)
- Owns IT operations, infrastructure, and service delivery
- Responsible for execution, reliability, and day-to-day performance
The CDIO will drive transformation through close partnership with the CIO, leveraging the existing IT organization to execute against the future-state vision.
Responsibilities:
Digital Strategy & Transformation
- Define and communicate a forward-looking technology vision aligned with organizational priorities
- Lead enterprise-wide digital transformation initiatives
- Identify and prioritize opportunities for automation, modernization, and innovation
- Evolve the technology operating model to support scale and agility
Data, AI & Innovation Leadership
- Establish and advance the organization’s data and AI strategy
- Identify practical applications of AI and automation across business functions
- Enable data-driven decision-making and operational workflows
- Translate emerging technologies into actionable business solutions
Enterprise Alignment & Change Leadership
- Partner with executive leadership to align technology initiatives with enterprise strategy
- Drive cross-functional coordination across departments
- Lead organizational change required to adopt new technologies and processes
- Serve as a visible leader and communicator of technology direction
Technology Portfolio Direction
- Shape the enterprise technology portfolio across IT, Product Development, and Kashrus systems
- Influence prioritization and investment decisions through governance structures (e.g., ITEC)
- Ensure alignment between technology investments and long-term organizational goals
External Perspective & Benchmarking
- Introduce external best practices and industry perspective
- Benchmark OU capabilities against peer and leading organizations
- Identify opportunities to accelerate progress through modern approaches
Success Metrics
- Measurable transformation of the technology function within 12–24 months
- Increased automation and reduction of manual processes
- Advancement of enterprise data and AI capabilities
- Improved responsiveness and communication across IT and business units
- Strong alignment between technology investments and organizational priorities
- Clear perception of organizational progress to a “next level” of technology maturity
Qualifications:
Experience
- 12+ years of leadership experience in digital transformation, technology strategy, or innovation roles
- Bachelor’s degree in computer science, Business Information Systems or related field.
- Proven experience leading enterprise transformation initiatives in complex organizations
- Experience working alongside operational IT leadership structures
Technical & Strategic Expertise
- Strong understanding of data, analytics, AI, and emerging technologies
- Ability to translate technical concepts into business outcomes
- Experience shaping enterprise technology strategy and execution
Leadership & Communication
- Demonstrated ability to drive change across organizational boundaries
- Strong executive presence and stakeholder engagement skills
- Ability to influence without direct control over all execution resources
Key Attributes
- Strategic thinker with strong execution awareness
- Comfortable operating in ambiguity and driving clarity
- Forward-looking, with a focus on practical innovation
- Collaborative leader capable of working across functions and leadership levels
Salary & Benefits:
The salary range for this (full-time) position is $300,000 - $400,000, commensurate with experience.
Health, Dental & Vision Insurance:
The OU offers health insurance through an Individual Coverage Health Reimbursement Arrangement (ICHRA). Instead of a single group plan, employees have the freedom to choose their own health insurance plan that fits their personal and family needs. The OU contributes a generous monthly amount directly toward your premium, making coverage more flexible, affordable, and tailored to you.
Employees enrolled in our health plan also receive an annual BeniComp stipend, a supplemental benefit that reimburses eligible medical, pharmaceutical, dental, and vision expenses.
In addition, the OU offers employees group dental and vision insurance through MetLife.
Additional Benefits and Perks:
- 10 Paid sick days
- 10 Paid vacation days
- Paid Jewish and Federal holidays
- Short Fridays to accommodate for Sabbath observance
- Free life and disability insurance
- Discounted continuing education opportunities
- 403(b) retirement plan with a 5% employer match after 3 years (requires a minimum 2% employee contribution)
