Remote Technical Program Manager Jobs in Chicago, IL

Position Summary

Join Deloitte's AI & Engineering practice to support Technical Program Management to lead the build of a custom NextGen point of sale solution for our client and roll it out to thousands of stores.

Recruiting for this role ends on 08/10/2026.

Work you'll do

The Technical Program Manager will lead end-to-end program management for large-scale retail technology transformation initiatives, including POS modernization, store systems, and enterprise platform deployments across thousands of locations. Define and maintain program roadmaps covering feature delivery, release cadence, deployment governance, and post-production support in alignment with business and technology objectives. Coordinate cross-functional stakeholders across Engineering, Product, QA, Infrastructure, and Store Operations to drive enterprise delivery alignment and accountability. Design and implement deployment strategies (e.g., A/B rollout, phased releases) to minimize production risk and reduce store downtime. Establish program KPIs, metrics, and ROI models; prepare executive and board-level reporting to support investment decisions and transformation funding

Manage multi-vendor delivery ecosystems, ensuring alignment, performance accountability, and predictable execution across onshore and offshore teams. Identify and implement AI-driven operational improvements, translating emerging capabilities into measurable business outcomes (cost savings, incident reduction, process efficiency). Conduct delivery health assessments and drive root-cause resolution to reduce production incidents and improve system stability. Lead program governance, risk management, and escalation frameworks across multi-million-dollar transformation portfolios. A successful candidate would possess these skills:

• Ability to work independently and collaborate as part of a team
• Effective written and verbal communication skills
• Meticulous attention to detail and quality of work product
• Ability to build and sustain professional relationships
• Ability to lead projects or workstreams
• Ability to manage and prioritize multiple tasks in a fast-paced and dynamic environment
• Strong interpersonal skills and professional demeanor
• Ability to meet deadlines

The team

AI & Engineering leverages cutting-edge engineering capabilities to build, deploy, and operate integrated/verticalized sector solutions in software, data, AI, network, and hybrid cloud infrastructure. These solutions are powered by engineering for business advantage, transforming mission-critical operations. We enable clients to stay ahead with the latest advancements by transforming engineering teams and modernizing technology & data platforms. Our delivery models are tailored to meet each client's unique requirements. Our Industry Solutions offering provides verticalized solutions that transform how clients sell products, deliver services, generate growth, and execute mission-critical operations. We deliver integrated business expertise with scalable, repeatable technology solutions specifically engineered for each sector.

Qualifications

Required:

• 8+ years leading end-to-end program management for large-scale retail technology transformation initiatives, including POS modernization, store systems, and enterprise platform deployments across thousands of locations.
• Experience defining and maintaining program roadmaps covering feature delivery, release cadence, deployment governance, and post-production support in alignment with business and technology objectives.
• Experience in designing and implementing deployment strategies (e.g., A/B rollout, phased releases) to minimize production risk and reduce store downtime.
• Establish program KPIs, metrics, and ROI models; prepare executive and board-level reporting to support investment decisions and transformation funding
• Experience in identifying and implementing AI-driven operational improvements
• Bachelor's degree, preferably in information technology, business, or related field; or equivalent experience
• Limited immigration sponsorship may be available
• Ability to travel 10%, on average, based on the work you do and the clients and industries/sectors you serve
• Role is remote

Preferred:

• Experience using Microsoft Word, Excel, and PowerPoint
• Experience supporting clinical or healthcare business operations
• Experience managing multiple projects or workstreams
• Experience preparing and delivering technical demonstrations
• Experience analyzing billing workflows, claim issues, or operational data

For individuals assigned and/or hired to work in a remote role, Deloitte is required by law to include a reasonable estimate of the compensation range for this role. This compensation range is specific to the remote role and takes into account the wide range of factors that are considered in making compensation decisions including but not limited to skill sets; experience and training; licensure and certifications; and other business and organizational needs. At Deloitte, it is not typical for an individual to be hired at or near the top of the range for their role and compensation decisions are dependent on the facts and circumstances of each case. A reasonable estimate of the current range is $140,000 to $180,000 with overtime pay possible.

You may also be eligible to participate in a discretionary annual incentive program, subject to the rules governing the program, whereby an award, if any, depends on various factors, including, without limitation, individual and organizational performance.

Information for applicants with a need for accommodation: https://www2.deloitte.com/us/en/pages/careers/articles/join-deloitte-assistance-for-disabled-applicants.html 

Position Summary

Join Deloitte's AI & Engineering practice to support Technical Program Management to lead the build of a custom NextGen point of sale solution for our client and roll it out to thousands of stores.

Recruiting for this role ends on 08/10/2026.

Work you'll do

The Technical Program Manager will lead end-to-end program management for large-scale retail technology transformation initiatives, including POS modernization, store systems, and enterprise platform deployments across thousands of locations. Define and maintain program roadmaps covering feature delivery, release cadence, deployment governance, and post-production support in alignment with business and technology objectives. Coordinate cross-functional stakeholders across Engineering, Product, QA, Infrastructure, and Store Operations to drive enterprise delivery alignment and accountability. Design and implement deployment strategies (e.g., A/B rollout, phased releases) to minimize production risk and reduce store downtime. Establish program KPIs, metrics, and ROI models; prepare executive and board-level reporting to support investment decisions and transformation funding

Manage multi-vendor delivery ecosystems, ensuring alignment, performance accountability, and predictable execution across onshore and offshore teams. Identify and implement AI-driven operational improvements, translating emerging capabilities into measurable business outcomes (cost savings, incident reduction, process efficiency). Conduct delivery health assessments and drive root-cause resolution to reduce production incidents and improve system stability. Lead program governance, risk management, and escalation frameworks across multi-million-dollar transformation portfolios. A successful candidate would possess these skills:

• Ability to work independently and collaborate as part of a team
• Effective written and verbal communication skills
• Meticulous attention to detail and quality of work product
• Ability to build and sustain professional relationships
• Ability to lead projects or workstreams
• Ability to manage and prioritize multiple tasks in a fast-paced and dynamic environment
• Strong interpersonal skills and professional demeanor
• Ability to meet deadlines

The team

AI & Engineering leverages cutting-edge engineering capabilities to build, deploy, and operate integrated/verticalized sector solutions in software, data, AI, network, and hybrid cloud infrastructure. These solutions are powered by engineering for business advantage, transforming mission-critical operations. We enable clients to stay ahead with the latest advancements by transforming engineering teams and modernizing technology & data platforms. Our delivery models are tailored to meet each client's unique requirements. Our Industry Solutions offering provides verticalized solutions that transform how clients sell products, deliver services, generate growth, and execute mission-critical operations. We deliver integrated business expertise with scalable, repeatable technology solutions specifically engineered for each sector.

Qualifications

Required:

• 8+ years leading end-to-end program management for large-scale retail technology transformation initiatives, including POS modernization, store systems, and enterprise platform deployments across thousands of locations.
• Experience defining and maintaining program roadmaps covering feature delivery, release cadence, deployment governance, and post-production support in alignment with business and technology objectives.
• Experience in designing and implementing deployment strategies (e.g., A/B rollout, phased releases) to minimize production risk and reduce store downtime.
• Establish program KPIs, metrics, and ROI models; prepare executive and board-level reporting to support investment decisions and transformation funding
• Experience in identifying and implementing AI-driven operational improvements
• Bachelor's degree, preferably in information technology, business, or related field; or equivalent experience
• Limited immigration sponsorship may be available
• Ability to travel 10%, on average, based on the work you do and the clients and industries/sectors you serve
• Role is remote

Preferred:

• Experience using Microsoft Word, Excel, and PowerPoint
• Experience supporting clinical or healthcare business operations
• Experience managing multiple projects or workstreams
• Experience preparing and delivering technical demonstrations
• Experience analyzing billing workflows, claim issues, or operational data

For individuals assigned and/or hired to work in a remote role, Deloitte is required by law to include a reasonable estimate of the compensation range for this role. This compensation range is specific to the remote role and takes into account the wide range of factors that are considered in making compensation decisions including but not limited to skill sets; experience and training; licensure and certifications; and other business and organizational needs. At Deloitte, it is not typical for an individual to be hired at or near the top of the range for their role and compensation decisions are dependent on the facts and circumstances of each case. A reasonable estimate of the current range is $140,000 to $180,000 with overtime pay possible.

You may also be eligible to participate in a discretionary annual incentive program, subject to the rules governing the program, whereby an award, if any, depends on various factors, including, without limitation, individual and organizational performance.

Information for applicants with a need for accommodation: https://www2.deloitte.com/us/en/pages/careers/articles/join-deloitte-assistance-for-disabled-applicants.html