[Hiring] Proposal Project Specialist @Cigna Healthcare

October 8, 2026

Role Description

The Proposal Project Specialist is responsible for managing the proposal development process for less complex, custom bids, from receipt of the RFP through proposal submission. This individual will have specialized knowledge of their primary business segment, with the ability to support other segments as needed. The Proposal Project Specialist is responsible for concurrently managing multiple proposals with aggressive deadlines. They support follow-up, finalist, and contracting activities, as needed.

Manage assigned proposal projects to include:
- Analysis, research, writing/editing responses to RFI/RFP questionnaires
- Negotiating requirements in any RFP questionnaires with appropriate cross-functional SMEs
- Creating proposal documents and other exhibits to support the defined sales strategy and strengths of company’s product and service offerings
Manage and facilitate requirements to ensure they are in line with the corporate position
Work with cross-functional SMEs to get agreements to requirements and increase overall requirements compliance
Execute proposal projects, including:
- Cross-functional team communications
- Timelines and follow-up
- Ensure accurate, complete and quality input from operational areas for on-time proposal production
Generate proposal and sales documents while adhering to corporate marketing standards, department guidelines, templates, and styles
Coordinate production and shipping to ensure accurate and on-time delivery
Resolve issues and conflicts with appropriate escalation
Serve as Proposal Management Subject Matter Expert for various matrix partners
Develop market and client industry specific responses as appropriate
Contribute to a culture of continuous improvements and share ownership of process improvement efforts
Display sound critical thinking skills and bring forth ideas
Actively participate in ad hoc projects and process ownership/responsibility
Provide training, coaching, and mentoring of new team members as it relates to proposals and/or projects applicable to the Proposal Project Specialist role

Qualifications

Bachelor’s degree in Business, Pre-Law, English, Journalism or Communication or equivalent work experience
Master’s degree highly preferred
Project management and previous proposal experience

Requirements

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

Company Description

Evernorth Health Services, a division of The Cigna Group, creates pharmacy, care and benefit solutions to improve health and increase vitality. We relentlessly innovate to make the prediction, prevention and treatment of illness and disease more accessible to millions of people. Join us in driving growth and improving lives.

Back to blog

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...