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Remote Annuity Jobs in Chicago, IL (NOW HIRING)

Let's Get to Work

Chicago, IL · Remote

$105K - $137K/yr

Life & Annuity Insurance Sales Agent -- 100% Remote | 100% Commission | Unlimited Earning Potential Location: Remote (Work From Anywhere) Compensation: 100% Commission -- Uncapped Income Potential ...

Basic Qualifications: * 1 year experience (WAH) remote customer service (Call Center environment ... Previous life insurance industry experience that required knowledge of life insurance and annuity ...

Basic Qualifications: * 1 year experience (WAH) remote customer service (Call Center environment ... Previous life insurance industry experience that required knowledge of life insurance and annuity ...

Legacy and Major Gift Planner

Aurora, IL · On-site +1

$65K - $74K/yr

Approved Remote Location Type of Role: Full-time; Salaried/Exempt Date: July 2026 About TEAM: TEAM ... Oversee and manage the Charitable Gift Annuity (CGA) program which includes marketing to donors and ...

Legacy and Major Gift Planner

Aurora, IL · Remote

$69K - $79K/yr

Approved Remote Location Type of Role: Full-time; Salaried/Exempt Date: July 2026 About TEAM: TEAM ... Oversee and manage the Charitable Gift Annuity (CGA) program which includes marketing to donors and ...

Life Insurance Agent

Chicago, IL · Remote

$50K - $100K/yr

Kimbrell Agency Remote Employment Type: Contractor Compensation $50,000 to $100,000 per year (plus ... life, health, annuity, disability and retirement policies with over $85 million in sales. The ...

Remote Annuity information

What is a remote annuity?

A Remote Annuity job typically involves selling, managing, or providing customer service for annuity products from a remote location, such as your home. Professionals in these roles may work for insurance companies, financial institutions, or as independent agents, supporting clients with their annuity purchases and ongoing account management. The job often includes educating clients about annuity options, processing applications, and ensuring compliance with regulations. Remote Annuity jobs leverage virtual communication tools to interact with clients and team members. This setup offers flexibility and the ability to work from anywhere with a reliable internet connection.

What are the key skills and qualifications needed to thrive as a remote annuity specialist?

To thrive as a Remote Annuity Specialist, you need a strong understanding of financial products, insurance regulations, and sales techniques, typically supported by relevant licenses such as a state insurance license. Proficiency in CRM software, online communication platforms, and financial planning tools is commonly required. Outstanding customer service, self-motivation, and the ability to clearly explain complex information are crucial soft skills for this remote role. These skills ensure effective client support, regulatory compliance, and successful sales performance in a virtual environment.

What are some common challenges faced by remote annuity specialists and how can they be addressed?

Remote annuity specialists often face challenges such as maintaining effective communication with clients and colleagues, staying updated on regulatory changes, and managing complex client portfolios without in-person interaction. To address these, it's important to leverage digital collaboration tools, participate in regular virtual training sessions, and establish clear communication channels. Staying organized and proactive in reaching out to clients also helps build trust and ensures seamless service delivery in a remote environment.

What is the difference between Remote Annuity vs Remote Insurance Agent?

AspectRemote AnnuityRemote Insurance Agent
CredentialsLicenses in annuities, financial certificationsInsurance licenses, certifications
Work EnvironmentRemote, client-facing, financial planningRemote, client-facing, sales-focused
Industry UsageFinancial services, retirement planningInsurance sales, risk management
Common Search IntentFinancial products, retirement incomeInsurance policies, coverage options

Remote Annuity professionals focus on selling and advising clients on retirement income products like annuities, requiring financial licenses. Remote Insurance Agents sell various insurance policies, needing insurance licenses. While both roles are remote and client-facing, their primary products and certifications differ, aligning with distinct industry segments.

What are the most commonly searched types of Annuity jobs in Chicago, IL?

The most popular types of Annuity jobs in Chicago, IL are:

What job categories do people searching Remote Annuity jobs in Chicago, IL look for?

The top searched job categories for Remote Annuity jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Annuity jobs?

Cities near Chicago, IL with the most Remote Annuity job openings:

Infographic showing various Remote Annuity job openings in Chicago, IL as of August 2026, with employment types broken down into 87% Full Time, and 13% Part Time. Highlights an 100% Remote job distribution.

External Wholesaler, Annuity Distribution

Massachusetts Mutual Life Insurance Company (MassMutual)

Chicago, IL • On-site, Remote

Full-time

Re-posted 12 days ago


MassMutual rating

7.8

Company rating: 7.8 out of 10

Based on 37 frontline employees who took The Breakroom Quiz

196th of 315 rated insurance


Job description

External Wholesaler
MMSD Annuity Distribution
Full-time, Remote IL, IN

The Opportunity
We're growing and our clients deserve the best. We are building a dynamic team of external wholesalers to drive the sales of MassMutual's Annuity Distribution to third party distributors. We are looking for a dynamic External Annuity Wholesaler. In this role you will build and grow relationships across our channel with Banks, Credit Unions, Wirehouse, National/Regional Broker Dealers, and Independent Broker Dealers in IL, IN. You will possess an entrepreneurial spirit, while striving for excellence. You will be responsible for territory production in partnership with an internal wholesaler, drive financial professional annuity penetration rates, and promote diversity of products sold through third-party distributors. You will have a strong desire to broaden financial wellness in a learning environment while providing education to communities throughout the assigned territory.
The Team
We have assembled a team of industry leading professionals making up our internal sales, key account management, advanced sales, and sales enablement & marketing teams. The team has a track record of focusing on the customer, collaboration and achieving sales results. The team is entrepreneurial in spirit and doesn't back away from a challenge. The team has built a great sense of community and desire to execute since the MMSD division was established in 2021.
The Impact:
As the External Wholesaler, MMSD Annuity Distribution, key responsibilities & competencies include:
  • Proactively develop, maintain, and grow annuity sales relationships with financial professionals of the Territory through ongoing financial professional profiling, continual relationship-building, and refining and refreshing financial professional base. This is done via in-person and virtual meetings, while documenting activities in Salesforce.
  • Execute on specific territory sales goals, activity expectations, and territory management with banks, credit unions, wirehouse, national/regional broker dealers, and independent broker dealers to maximize opportunities.
  • Develop and execute a strategic territory business plan, coordinate linkage between segmentation strategy and zones/rotation execution to drive top line revenue and sales results. Complete minimum of 20 in-person meetings per week.
  • Deep understanding and knowledge of annuity products, positioning, associated riders, and sales concepts while gaining industry knowledge and insights on market trends, demonstrate understanding of the annuity industry and competitive landscape.
  • Subject Matter Expert for MMSD Annuity products and positioning, be viewed as a resource for financial professionals for competitive situations.
  • Understand the selling process, including questioning techniques to discover and confirm client needs, strong listening skills, acknowledging of client questions, concerns, and overcoming objections. Demonstrate proficiency of sales presentations skills, both virtual and in person, demonstrate advanced presentation skills for variety size of audience, ability to present with a high degree of audience participation and buy-in. Possess experience with a variety of presentation medium (Zoom, PowerPoint, etc.).
  • Communicate confidently with your customer base to drive sales in partnership with your territory's internal wholesaler, speak & present ideas effectively, communicating in person, virtually, in writing, phone, e-mail, and other methods, possess effective conflict resolution.
  • Optimize time management by prioritizing high-value tasks, streamlining communications with financial professionals and team members, while managing utilization and allocation of resources appropriately and efficiently.
  • Be trustworthy, adhere to high ethical standards, adhere to the letter and spirit of applicable laws, rules, regulations, and company policies. Ability to be seen as trusted and valued business partner. Lead by example and inspire trust.
  • Effectively partner with internal wholesaler, new business, key account manager team, and relationship management team on escalations/prioritizations in territory to achieve goals.
  • Travel- up to 90% Travel required, manage travel & expense budget, maximization of budget resources.
  • Other duties as assigned.

The Minimum Qualifications
  • 3+ years of experience in annuity or investment solutions sales experience.
  • 2+ years of experience with Word, Excel, PowerPoint, and Salesforce as well as various internet search tools.
  • State Life and Health License.
  • FINRA Series Licenses 6 or 7 at time of application.
  • State Securities License Series 63 license at time of application.
  • High School Diploma.
  • Ability to travel upwards of 90% within territory.
  • Reside in Chicago, IL, or within the territory IL or IN.

The Ideal Qualifications
  • Bachelor's degree.
  • Experience in all channels of annuity distribution, especially variable annuity distribution.
  • 5+ years of experience in annuity wholesale distribution.
  • 2+ years of experience in an external wholesaling position.
  • Possess excellent oral and written communication skills, interpersonal and customer service skills.
  • Possess excellent public speaking skills and presentation skills to groups of varying sizes in person and virtually.
  • Strong relationship building skills & sense of time management.
  • Must be detailed-oriented and well-organized self-starter with high energy and creativity.
  • Proven ability to multitask and attention to detail.

Compensation: $65K-$85K base range plus sales-based incentive opportunity resulting in a total target compensation package of $200-$400K.
What You Can Expect at MassMutual
MassMutual offers the opportunity to do meaningful work within a purpose-driven organization that values long-term impact over short-term outcomes. In this role, you can expect:
Clear areas of ownership and accountability, with work that connects directly to company and customer outcomes
A collaborative environment where perspectives are welcomed
Access to learning, development, and internal networks that support continuous growth and skill-building over time
Employee-led communities and forums that foster connection, learning, and inclusion across the organization
A culture grounded in integrity, responsibility, and stewardship-supported by a company with a strong legacy and a future-focused mindset
#LI-RS1
#LI-REMOTE
Why Join Us.
We've been around since 1851. During our history, we've learned a few things about making sure our customers are our top priority. In order to meet and exceed their expectations, we must have the best people providing the best thinking, products and services. To accomplish this, we celebrate an inclusive, vibrant and diverse culture that encourages growth, openness and opportunities for everyone. A career with MassMutual means you will be part of a strong, stable and ethical business with industry leading pay and benefits. And your voice will always be heard.
We help people secure their future and protect the ones they love. As a company owned by our policyowners, we are defined by mutuality and our vision to put customers first. It's more than our company structure - it's our way of life. We are a company of people protecting people. Our company exists because people are willing to share risk and resources, and rely on each other when it counts. At MassMutual, we Live Mutual.
MassMutual is an Equal Employment Opportunity employer. We welcome all persons to apply.
If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
At MassMutual, we focus on ensuring fair, equitable pay by providing competitive salaries, along with incentive and bonus opportunities for all employees. Your total compensation package includes either a bonus target or in a sales-focused role a Variable Incentive Compensation component. For more information about our extensive benefits offerings please check out our Total Rewards at a Glance.

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