Chief Information Officer

City of Chesapeake, VA | Full-time


The Position

The City of Chesapeake is seeking a customer-focused Chief Information Officer who will develop an IT strategic plan, continue modernizing the City’s IT systems, and oversee the Chesapeake Connects fiber project. The City desires a CIO that can move the department into a more strategic business model to support the priorities of the City and improve service delivery to internal and external customers.

The position is responsible for leading staff, establishing goals, objectives, policy and procedures, planning information system infrastructure and architecture, designing operating processes, managing system operations, evaluating system performance, negotiating for improved system capabilities, and coordinating or reporting on activities to senior management and elected or appointed officials. This position researches and formulates long-range goals for the organization and develops policy and position papers and works on a variety of issues with the chief administrative officer and senior staff. The position also includes presenting to various audiences, including elected officials.

The CIO reports directly to the Deputy City Manager for Internal Services and serves as the key advisor to the City Manager on IT issues. The CIO serves as a member of the City Manager’s Strategy and Governance Team. This committee meets with the City Manager and advises the City Manager on organization-wide issues and strategies. This role is for a strategic leader who can put on an organization-wide hat and be a key partner in achieving the City’s strategic outcomes.


  • Develop strong working relationships with the City Manager’s Office, IT staff, and all city departments. Learn the operations and needs of each business unit within the City.
  • Oversee the launching of Chesapeake Connects, a large middle mile fiber infrastructure project breaking ground in summer 2022. This project will connect the City to key partners in Chesapeake and the Southside Network Authority regional ring. It will enhance education and public safety response, expand healthcare, and spur economic development.
  • Implement the Tax System Modernization project moving from a legacy to a modern system.
  • Build on the City’s commitment to enhance its Cybersecurity program by working with the City Manager’s Office and Systems Security Manager.
  • Improve the customer experience of user departments and identify the most effective way to meet the service needs of City departments to best support the overall strategic outcomes of the City.
  • Develop an IT strategic plan and/or Technology Improvement Plan in collaboration with City leaders and determine the prioritization of key projects and initiatives

The Successful Candidate

The next Chief Information Officer will be a leader of people with expertise in the IT field. The ideal candidate has a proven track record of achieving great results while building positive relationships inside and outside the organization. The next CIO will be able to listen to the needs of city users and bring creative technical solutions by utilizing the combined knowledge of users and IT professional staff. The successful candidate will have a collaborative and creative approach to internal service delivery. The ideal candidate will be a welcoming face to the organization and will develop meaningful relationships with the IT staff team, city leadership, and departments.

The successful candidate will be a change agent poised to lead the IT department to a new level of partnership with its business units, with knowledge of effective project management, and change management principles. Not only does the next Chief Information Officer need to be a technical expert, but they must be equally skilled in communication, trust-building, management, and leadership. The ideal candidate is a quick learner that can prioritize the customer service aspect of the department concurrent to delivering key strategic projects that are important for the City to succeed.

The successful candidate is outcome-focused and recognizes the future needs of the department and will develop a clear workplan to get there. The CIO knows how to lead the staff by collaborating with different workstyles of staff, clarifying expectations, and providing support to help the whole department succeed. The next Chief Information Officer needs to be comfortable with juggling different roles and will anticipate challenges while maintaining a positive attitude.

The successful candidate will be highly skilled at communicating IT concepts and advocating for needs and opportunities to a variety of audiences. This effort will include close collaboration with the Deputy City Manager for internal services, the Internal Customer Service Functional Team, and the City Manager’s Strategy and Governance Team.


Minimum requirements include any combination of education and experience equivalent to a bachelor’s degree in computer science, information technology, management information systems, business administration, or a closely related field. A minimum of six years of full-time equivalent experience with responsibilities in the management and support of information systems and technology is also required.

Preferred qualifications include leadership of an IT staff team, demonstrated experience with improving customer service, upgrading key systems, addressing cybersecurity in a complex environment with multiple lines of business, supporting a digital workforce, and developing a culture of service and partnership with departments. Local government IT experience is preferred but not required.

About Chesapeake’s Government

The City operates under the Council-Manager form of government. The council-manager form of local government combines the political leadership of elected officials with the managerial experience of a professional city manager. Chesapeake has eight council members and a mayor elected at large, which means that members represent the entire city rather than specific districts.

As Chesapeake's legislative body, the City Council establishes priorities, approves the budget, and sets the tax rate. Council members hire the City Manager, who, as the organization’s Chief Executive Officer, is responsible for the day-to-day administration of the City and serves as the Council's chief advisor. The City Manager recommends a budget, sets direction, and establishes policies to carry out the Council's priorities.

The City government employs approximately 3,500 people in more than 30 departments. The Approved Operating Budget for FY 2023 is $1.48 Billion and includes $728 Million for Schools. The Information Technology budget is $22.7 Million. 

The Capital Budget appropriated for FY 2023 is $255 Million with a five-year plan of just over $749 Million. The Information Technology projects represent $26.4 Million with $47.4 Million in the five-year plan.

Chesapeake is a full-service city. The community has a long history of stability and prides itself on an innovative, professional staff. The next CIO will be expected to be customer-focused and have strong personal relationships with all of the stakeholders in city government.

The City organization has a set of organizational values, known as the CARES standards, which the staff embodies as they carry out the work of the City. These organizational values stipulate that, as employees perform their work for and on behalf of the residents of and visitors to Chesapeake, they are:

Courteous – Making customers feel welcome, appreciated, and respected.

Attentive – Enhancing the ability to identify the needs and concerns of customers.

Responsive – Acting upon customers’ needs and providing follow-up in a timely manner.

Empowered – Possessing the knowledge, resourcefulness, creativity, and integrity to address customers’ needs.

Stewards – Demonstrating a commitment to public service, the safety of ourselves, our coworkers, and our community, and being good stewards of our financial & environmental resources.

Inside the IT Department

The Information Technology department is more than just data and connections. It’s strategy. It's vision. Information Technology helps City departments use technology to provide better services to citizens more efficiently.

The Information Technology department FY2023 Budget FTEs is 73 employees plus several contractors. The department’s management team includes the Deputy Director, Systems Security Manager, Network Services Coordinator, IT Enterprise Operations Manager, GIS Administrator, Strategic Technology Manager, Fiscal Administrator, Systems Analyst III, and Software Engineer III.

The Information Technology department aligns its efforts with the City Council Objectives. On Council’s connectivity objective, Information Technology has taken the time to plan and implement city-wide fiber and wireless solutions to connect City, Schools, and Library resources. These broadband resources will enhance the City’s economic viability to attract more businesses and entrepreneurs who may wish to call Chesapeake home. The broadband and wireless infrastructure will be the catalyst for smart city initiatives that can improve our environment and quality of life in Chesapeake. Most of all, these technologies will allow for more robust and capable public safety for our citizens.

The Information Technology department has been working to expand the City’s ability to address a more mobile and virtual work environment. Information Technology has been working to create a platform that can support a digital workforce and smart city. These efforts have allowed the City to address the ever-changing work environment. As the department expands these technologies, they plan to address citizens’ capabilities as well so citizens can more easily interact with City services.

IT systems include:

  • Finance & Procurement – PeopleSoft
  • Human Resources, Payroll, and Timekeeping – Munis and UKG
  • Tax System – legacy mainframe system being upgraded to a new system; vendor selection in process at the time of publication
  • Planning and permitting – Accela
  • Geospatial platform – ArcGIS Enterprise
  • Public Safety – Tyler/New World Computer Aided Dispatch (CAD) and Records Management System

The Community

Chesapeake is the second largest city in Virginia and one of America’s 100 largest cities. Situated near the world’s largest natural harbor and the world’s largest naval base, Chesapeake is located within 20 minutes of the Virginia Beach oceanfront, 15 minutes from downtown Norfolk, and one hour from Colonial Williamsburg and the Outer Banks of North Carolina. Chesapeake offers an endless range of outdoor activities, terrific shopping, phenomenal food, and beautiful wildlife. Here you will find an impressively diverse collection of geography encompassing urban delights, rural masterpieces, and an endless menu of outdoor options and indoor fun. It’s a community of communities, each with a distinctive history.

Chesapeake has been ranked as one of the best places to live by Money magazine. It is a vibrant community that enjoys the best of two worlds: one of urban variety, culture, and excitement, and another of rural landscapes and relaxed country living. It is also consistently ranked by the FBI as one of the five safest U.S. cities with populations over 200,000, which lends to the safe, community atmosphere that residents enjoy.

Chesapeake has more miles of deep-water canals than any other city in the country and is part of the Intracoastal Waterway, stretching from Maine to Florida. Over the last decade, many national and international companies have taken advantage of the City’s port-related activities, atmosphere, and highly qualified labor market by relocating to Chesapeake. The City is home to the Dollar Tree corporate headquarters.

Chesapeake is considered a premier community in the Hampton Roads area. It has a high median annual household income and strong employment diversification. Single-family homes are the most common housing type in Chesapeake. Diverse neighborhoods offer a high quality of living with strong connections in the communities.

The Chesapeake Public Schools system serves over 39,000 students with almost 5,700 teachers, administrators, and various support personnel. With seven high schools, ten middle schools, twenty-eight elementary schools, Chesapeake Career Center, Chesapeake Center for Student Success, and Chesapeake Virtual Academy, the school district is dedicated to high levels of performance.

The school district has the highest on-time graduation rates and one of the lowest drop-out rates in the Commonwealth. Academics, athletics, and the arts are carefully balanced from the primary level through the comprehensive high school curriculum. A strong emphasis on basic skills in the four core subject areas and technology at all levels enhances instruction. A wide variety of course options provide a unique and diverse curriculum that challenges those students who enroll.

Based on the City’s pro-business climate, Chesapeake’s economy continues to generate multi-million-dollar business investments and high-demand jobs year after year. Five major business districts are concentrated in the northern half of the City, comprising one of the strongest business climates in the Mid-Atlantic region. Chesapeake’s economy is recognized as one of the strongest and most highly skilled workforces in the U.S. The area has achieved great success in recruiting and retaining new and existing companies that have an impact and strong community presence. Known for its excellent telecommunications and transportation infrastructure, Chesapeake has become a desired location for businesses.

Quick Facts

  • Population (2021): 251,269
  • Median Household Income (2020): $81,261
  • Median Home Value (2016-2020): $286,000
  • Median Age: 36.9

All demographic information was sourced from the U.S. Census Bureau.

Compensation and Benefits

The expected hiring range is $170,000 – $190,000, depending on qualifications, with an excellent benefits package. There is no residency requirement, but the City will provide relocation assistance for out-of-area candidates as part of the overall compensation package.

Benefits offered include the following:

  • Medical, dental, vision, life, and disability insurance
  • Participation in the Virginia Retirement System (VRS)
  • 457 Deferred Compensation Plan
  • Optional Life Insurance
  • Holiday, vacation, sick, and parental leave
  • Flexible spending accounts (FSA/HSA)
  • Employee Assistance Program (EAP)
  • Tuition and Skills Development Reimbursement
  • Employee Wellness Program
  • Pre-Paid Legal Services Plan
  • Deferred Compensation

How to Apply

Applications will be accepted electronically by Raftelis. Applicants complete a brief online form and are prompted to provide a cover letter and resume. The position will be open until filled with the first review of applications beginning October 3, 2022.


Please direct questions to Catherine Tuck Parrish at and Alexa Worrell at

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