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Worksite Sales RFP Specialist - REMOTE ID-17380

June 5, 2025

Job Details

The stated pay range is based on a national-average location. Actual salary is determined by factors including relevant work experience, skills and location. This position is bonus eligible.

CNO Financial Group's Optavise is hiring a Worksite Sales RFP Specialist to be responsible for managing and delivering Request for Proposals (RFP) and Request for Information (RFI) responses to help Optavise scale into new, unique accounts.

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This is your opportunity to collaborate closely with Sales, Finance, Solutions, Legal, Product, Marketing and other teams to ensure responses are accurate, high-quality, and aligned with our brand.

As a Worksite Sales RFP Specialist, your responsibilities will include:

Owning the end-to-end RFP and questionnaire response process for both Worksite distribution teams, delivering responses for Voluntary Benefits and Benefit Services RFPs and RFIs.
Coordinating input from Sales, Product, Solutions, Finance, Legal, and other stakeholders to ensure accurate, timely responses.
Drafting and refining written answers to technical, functional, and business questions in RFPs and RFIs.
Establishing and maintaining a scalable, up-to-date knowledge base of commonly asked questions and approved answers, levering Loopio, our RFP management tool.
Managing an RFP response platform (Loopio) and corresponding library of content to ensure accuracy and readiness.
Managing external Customer & Broker RFP/RFI vendor profiles (e.g., Shortlister, responsive, etc.).
Partnering with Sales leadership to track and improve RFP win rates and turnaround times.
Identifying opportunities to improve processes, templates, and collaboration across teams.
Ensuring all responses are aligned with Optavise tone, brand, and positioning.
Implementing, managing and optimizing use of RFP/Contract data and tools (e.g., GovSpend, EZGovOpps, GovWin IQ, etc.) to provide sales leadership with information on future contracting opportunities, targets and prospects.

The Worksite Sales RFP Specialist position is well suited for you if you:

Have experience working on RFPs or questionnaires in a B2B SaaS or fintech environment.
Are comfortable working cross-functionally with technical and non-technical stakeholders.
Use data to influence long-term sales and product strategies.
Possess proven project management skills and ability to manage multiple, concurrent deadlines.
Are an excellent communicator with strong editing skills, with attention to both detail and clarity.
Have supported enterprise sales or go-to-market teams.
Possess a strong sense of ownership, bias for action, with outstanding customer service and ability to collaborate effectively across the organization.

What you'll need:

Bachelor's degree in Public Relations, Communication/Rhetoric, Marketing, Business Administration or equivalent.
Three years of communication, marketing or PR experience in healthcare, insurance, or employer benefits market.
Familiarity with RFP software tools (e.g. Loopio, RFPIO, Responsive).
Experienced in proposal writing, technical writing, or solution consulting.

What will set you apart:

Master's degree in Public Relations, Communication/Rhetoric, Marketing, Business Administration or equivalent.
Five years of communication, marketing or PR experience in the healthcare, insurance, or employer benefits market the ability to
Candidate location in Central or Eastern US time zone is preferred OR willingness to work Central or Eastern time zone business hours.

The Company offers the following benefits for this position, subject to applicable eligibility requirements:

medical insurance
dental insurance
vision insurance
401(k) retirement plan with company match
short-term & long-term disability insurance
Paid time-off and corporate holidays,
paid parental leave
company paid life insurance

Click on this link for additional information.

CNO embraces flexibility and encourages you to work where you're most productive. Associates who live within a 60-mile radius of a corporate office (Birmingham, Carmel, Chicago, Orlando and Milwaukee) have access to come into that office.

Associates who live outside of a 60-mile radius of a corporate office (Birmingham, Carmel, Chicago, Orlando and Milwaukee) may perform this role full-time work from home (WFH) from any US based location, as long as you are willing to work central or eastern time zone hours.

All associates may be asked to travel to varying corporate offices periodically. Work cannot be performed from outside of the United States.

Optavise is a trusted benefits partner for business owners and human resources professionals who work hard to build and maintain a healthy, happy workforce. Through Optavise's cohesive suite of products and services, we guide employers and employees through their healthcare choices to help reduce costs and increase benefits engagement. We streamline administration for employers and educate employees about benefits and care options, making it easy for them to choose and use their benefits wisely. Optavise provides a first-of-its-kind benefits solution, including:

Benefits administration technology for a streamlined enrollment process
Customizable selection of voluntary benefits that employees want and need
Year-round benefits education, communications and advocacy to inform and empower employees to become better healthcare consumers
Expert resources, helping employees maximize their benefits and make more informed choices for themselves and their family members.

Our goal is to help people make good healthcare decisions. By simplifying administration and making benefits easier to understand, we help drive employee engagement and satisfaction, and save employers time and money.

Optavise is the worksite marketing brand of CNO Financial Group. CNO provides life and health insurance, annuities, financial services, and workforce benefits solutions through our family of brands and supported by our associates and agents. Our customers work hard to save for the future, and we help protect their health, income and retirement needs with 3.2 million policies and more than $35 billion in total assets. Our 3,400 associates, 8,600 exclusive agents and independent partner agents guide individuals, families and businesses through a lifetime of financial decisions.

We are financially strong and well positioned for continued growth, and we are grounded in our core values of Diversity, Equity & Inclusion (DE&I); Integrity, Customer Focus, Excellence, and Teamwork. We have offices in more than 260 communities in the U.S., including our headquarters in Carmel, Indiana, and corporate offices in Birmingham, Chicago, Philadelphia, Orlando and Milwaukee.

At CNO Financial Group, we're always looking forward-to the security and stability we help create for our insurance brands' customers, and the growth we create within our own company. We're looking for ambitious people who want to do more. We'll provide you with opportunities to grow your skills through challenging professional experiences.

If you're looking for a culture that encourages development, helps you reach your potential, and rewards you for your contribution, then CNO Financial Group is right for you. For more information, visit CNOinc.com.

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation.

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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...

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Worksite Sales RFP Specialist - REMOTE ID-17380

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

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

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

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

5. HOW DO YOU PROCESS INFORMATION?

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

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

8. HOW TO PRIORITIZE WORK?

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

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