Director of Digital Transformation and Learning

Nature of Work

The Director of Digital Transformation and Learning plays a vital role in advancing the City of Rochester’s commitment to high performance government by strengthening organizational effectiveness through technology, learning, and innovation. Reporting to the Deputy City Administrator for High Performance Government, this position focuses on empowering staff to confidently and responsibly use artificial intelligence (AI), automation, data, and broader digital tools—alongside strong business analysis and process improvement practices—to enhance public services, increase efficiency, and deliver measurable community outcomes. This role operates at an enterprise level, partnering across departments to identify opportunities for improvement, build workforce capability, and support the adoption of practical, scalable solutions. A key responsibility is leading technology learning and development efforts, ensuring City staff have the skills, tools, and confidence needed to succeed in a rapidly evolving digital environment. The Director serves as a bridge between business needs and technology, translating complex concepts into actionable strategies while fostering a culture of continuous improvement, innovation, and responsible use of emerging technologies.

Duties And Responsibilities

• Lead Organizational Technology Learning & Development
• Develop a structured digital fluency framework to build baseline and advanced competencies across the workforce.
• Assess organizational skill gaps and training needs, aligning and leading learning priorities with City strategic goals.
• Create engaging, hands-on training content using real City use cases to drive practical application.
• Evaluate learning effectiveness through adoption metrics, feedback, and performance outcomes, continuously improving offerings.
• Partner with departments to build confidence and independence in using digital tools to improve daily work.
• Identify and evaluate opportunities to leverage AI, automation, data, and other digital tools to improve City operations.
• Support the design and implementation of practical, scalable solutions aligned with organizational priorities.
• Conduct pilots and evaluations of emerging technologies to determine suitability for municipal use.
• Translate complex technical concepts into clear, actionable recommendations for staff and leadership.
• Document and communicate outcomes, including measurable improvements in service delivery, efficiency, and user experience.

• Lead and support change management efforts to ensure successful adoption of new tools, processes, and practices.
• Promote a culture of innovation, continuous improvement, and learning across the organization.
• Develop and share success stories, replicable practices, and lessons learned to scale impact.
• Engage with regional, community, and educational partners to support digital literacy and innovation initiatives.

• Perform Other Duties As Assigned Or Necessary.

Minimum Qualifications

• A Bachelor’s Degree in Information Systems, Data Science, Learning Design, Project Management, AI Engineering or a related field, and five (5) years of experience in business analysis, systems analyst, learning and development, digital transformation, or a related role.
• OR A Master's degree in Information Systems, Data Science, Learning Design, Project Management, AI Engineering and one (1) year of full-time employment experience in business analysis, systems analyst, learning and development, digital transformation, or a related role.
• OR An equivalent combination of education or experience.

Desirable Qualifications

• Experience in training, facilitation, change management, or enterprise initiatives is preferred.

Additional Information

• PHYSICAL AND ENVIRONMENTAL CRITERIA
• In compliance with the Americans with Disabilities Act, the following represents the physical and environmental demands for this position. The employee must be able to perform the essential functions with or without accommodation. In consideration of the overall amount of physical effort required to perform this position, the work is best described as Sedentary Work : Exerting up to 10 pounds of force occasionally and/or a negligible amount of force frequently or constantly to lift, carry, push, pull or otherwise move objects, including the human body. Sedentary work involves sitting most of the time. Jobs are sedentary if walking and standing are required only occasionally and all other sedentary criteria are met. Physical demands that may be required continuously (2/3 or more of the time), frequently (1/3 to 2/3 of the time), and occasionally (up to 1/3 of the time) are noted below: Continuous demands: sitting, fine dexterity, Frequent demands: standing, walking, reaching, handling, Occasional demands: lifting, carrying, pushing/pulling, kneeling, crouching, crawling, bending, twisting, climbing, balancing. Sensory requirements necessary in the performance of the essential functions of this position include sight, hearing, and touch. Environmental conditions that may exist in the performance of the essential functions of this job include: NONE (not substantially exposed to environmental conditions).