Jobs › Cigna

Application Development Senior Advisor- Hybrid

Cigna · Chicago, IL · $153,317–$203,600 a year · Full time

Posted Jun 1, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you had to give an effort estimate for a new project and the scope was still fuzzy. How did you get to a number you could stand behind?

What they are checking: Whether they estimate honestly with stated assumptions, since the Solution Architect and Delivery Lead plan around their numbers.

Tell me about a time a business partner wanted a call flow designed one way and you thought it would hurt the customer experience.

What they are checking: Whether they can push back with evidence while still respecting the business owner's decision.

Describe a production issue in a voice or chat application you supported. How did you find the cause?

What they are checking: Whether they can troubleshoot methodically across telephony, language understanding and back-end integrations under pressure.

What would you do

You find that a change in another team's release is about to break your call flow a week before go-live. What do you do?

What they are checking: Whether they protect application integrity across releases by raising cross-capability issues early and clearly.

This is a large transformation program across many lines of business. How do you build components so the next team can reuse them instead of rebuilding?

What they are checking: Whether they design for reuse and standards, which matters more than speed on an enterprise-wide program.

About the work

Walk me through a conversational IVR call flow you built. What was the caller trying to do, and how did you design the path so they didn't end up stuck or transferred for no reason?

What they are checking: Whether they think about the caller's goal and failure paths, not just wiring prompts and menus together.

How do you handle a caller who says something the natural language model doesn't recognize, twice in a row?

What they are checking: Whether they plan for no-match and no-input handling, which is where most voice experiences frustrate people.

What's your approach to unit and component testing for a voice or chat application, where the input is spoken language and not a clean form field?

What they are checking: Whether they can test conversational systems with real utterance variety instead of only the happy path.

How would you carry customer context from a chat session into a voice call so the person doesn't have to repeat themselves?

What they are checking: Whether they understand cross-channel integration and the data handoffs that make service feel personalized.

Healthcare callers often share member IDs, prescriptions and health details. How does that change the way you design and log a conversational app?

What they are checking: Whether they treat protected health information carefully in prompts, logs and recordings without being told.

What metrics would you look at after launching a new conversational IVR to decide if it's actually working?

What they are checking: Whether they measure containment, transfers and abandonment together, rather than chasing one number that can be gamed.

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The full job description

As published by Cigna.

Cigna-Evernorth Services, Inc. seeks an Application Development Senior Advisor for the Chicago, IL location to act as a senior software engineer responsible for developing tools, patterns, and processes. Responsibilities: • Responsible for evaluating and improving processes around continuous integration, continuous deployment, automation, quality engineering, security, and cost management. • Support Software Engineers, QA, Product Management, and Support teams and work closely with System Architecture and Software Engineering leadership teams. • Design and develop and advance team capabilities in Continuous Integration / Continuous Deployment for Cloud and on-premise applications. • Collaborate with Application Development teams on DevOps patterns, best practices, approved technologies and tools. • Collaborate with technical, application, and security leads to deliver a reliable and secure platform in cloud. • Provide technical governance for infrastructure design, deployment, and operations. • Strive for continuous improvement and build continuous integration, continuous development, and constant deployment pipeline (CI/CD pipeline). • Design DevOps components to manage within applications. • Hybrid work schedule. Qualifications: • Bachelor’s degree in Computers or Engineering and 5 years of any IT experience in the healthcare domain. • Will also accept a Master’s degree and 3 years of experience. • Must have experience with: scripting, including Python, PowerShell, and Shell scripting; • Splunk; Cloudwatch; Okta; ISAM; ECS; • Liquibase and Flyway for Aurura Postgre SQL; • MS SQL; Oracle; and • Control systems, including GitLab, GitHub, and TFS. • https://jobs.thecignagroup.com/us/en/benefits Salary Range: $153,317-$203,600 If you will be working at home occasionally or permanently, the internet connection must be obtained through a cable broadband or fiber optic internet service provider with speeds of at least 10Mbps download/5Mbps upload. For this position, we anticipate offering an annual salary of 122,200 - 203,600 USD / yearly, depending on relevant factors, including experience and geographic location. This role is also anticipated to be eligible to participate in an annual bonus plan. At The Cigna Group, you’ll enjoy a comprehensive range of benefits, with a focus on supporting your whole health. Starting on day one of your employment, you’ll be offered several health-related benefits including medical, vision, dental, and well-being and behavioral health programs. We also offer 401(k), company paid life insurance, tuition reimbursement, a minimum of 18 days of paid time off per year and paid holidays. For more details on our employee benefits programs, click here . About The Cigna Group Doing something meaningful starts with a simple decision, a commitment to changing lives. At The Cigna Group, we’re dedicated to improving the health and vitality of those we serve. Through our divisions Cigna Healthcare and Evernorth Health Services, we are committed to enhancing the lives of our clients, customers and patients. Join us in driving growth and improving lives. Qualified applicants will be considered without regard to race, color, age, disability, sex, childbirth (including pregnancy) or related medical conditions including but not limited to lactation, sexual orientation, gender identity or expression, veteran or military status, religion, national origin, ancestry, marital or familial status, genetic information, status with regard to public assistance, citizenship status or any other characteristic protected by applicable equal employment opportunity laws. If you need a reasonable accommodation to complete the online application process, please email seeyourself@thecignagroup.com for assistance. Please note that this email inbox is dedicated to accommodation requests only and cannot provide application updates or accept resumes. The Cigna Group has a tobacco-free policy and reserves the right not to hire tobacco/nicotine users in states where that is legally permissible. Candidates in such states who use tobacco/nicotine will not be considered for employment unless they enter a qualifying smoking cessation program prior to the start of their employment. These states include: Alabama, Alaska, Arizona, Arkansas, Delaware, Florida, Georgia, Hawaii, Idaho, Iowa, Kansas, Maryland, Massachusetts, Michigan, Nebraska, Ohio, Pennsylvania, Texas, Utah, Vermont, and Washington State. Qualified applicants with criminal histories will be considered for employment in a manner consistent with all federal, state and local ordinances.

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