2

Remote Learning Enablement Jobs in Chicago, IL (NOW HIRING)

... sales enablement for enterprise technology solutions * Ability to engage with executive ... Remote Zones offers a comprehensive benefits package While we're committed to providing top-tier ...

Technical Solutions Architect, AI

Chicago, IL · Remote

$68.25 - $82.50/hr

... sales enablement for enterprise technology solutions * Ability to engage with executive ... Remote Zones offers a comprehensive benefits package While we're committed to providing top-tier ...

They are fully remote and growing fast. How long has the company been operating? 2017 Total company ... Collaborate on launch planning and enablement, including documentation, demos, sales materials ...

High Ticket Sales Director

Chicago, IL · Remote

$120K - $250K/yr

Managing Top Performing Fully Remote Sales Teams! Position Overview: As an outsourced sales company ... You LOVE learning new things & having fun at the same time You SHOULD NOT apply to this role if:

Sales Director

Chicago, IL · Remote

$120K - $250K/yr

Managing Top Performing Fully Remote Sales Teams! Position Overview: As an outsourced sales company ... You LOVE learning new things & having fun at the same time You SHOULD NOT apply to this role if:

Showing results 41-51

Remote Learning Enablement information

What is remote learning enablement?

Remote Learning Enablement refers to the strategies, tools, and support systems that help individuals or organizations successfully conduct learning activities outside of traditional, in-person settings. This can involve the use of technology platforms, digital resources, instructional design, and ongoing technical support to ensure learners have access to quality education from any location. Professionals in this field often work to implement best practices, train educators, and troubleshoot issues to create effective and engaging remote learning experiences.

What are some common challenges faced by professionals in remote learning enablement, and how can they be addressed?

Professionals in Remote Learning Enablement often encounter challenges such as maintaining learner engagement, ensuring smooth technology adoption, and supporting diverse learning needs across distributed teams. Overcoming these challenges involves leveraging interactive tools, providing clear onboarding for digital platforms, and fostering open communication with both instructors and learners. Collaborating closely with IT, instructional designers, and organizational leaders helps to continuously improve the remote learning experience and resolve issues promptly.

What are the key skills and qualifications needed to thrive in remote learning enablement, and why are they important?

To thrive in Remote Learning Enablement, you need expertise in instructional design, digital pedagogy, and a solid understanding of e-learning best practices, often supported by a degree in education or instructional technology. Familiarity with Learning Management Systems (LMS) like Canvas or Moodle, authoring tools such as Articulate Storyline, and relevant certifications (e.g., Certified Professional in Learning and Performance) are highly valuable. Strong communication, problem-solving, and adaptability enable effective collaboration and support for diverse learners and educators in virtual environments. These competencies are essential to create engaging, accessible, and impactful remote learning experiences that drive learner success.

What is the difference between Remote Learning Enablement vs Instructional Designer?

AspectRemote Learning EnablementInstructional Designer
CredentialsTypically requires education or training in education, e-learning, or related fieldsUsually holds degrees in education, instructional design, or related disciplines
Work EnvironmentPrimarily remote, supporting online learning platforms and toolsOften remote or hybrid, designing and developing educational content
Employer & IndustryEducational institutions, corporate training, e-learning companiesEducational institutions, corporate training, e-learning firms
Primary FocusEnabling effective online learning experiences through support and technologyCreating and designing instructional materials and curricula

Remote Learning Enablement focuses on supporting and facilitating online education through technology and support roles, while Instructional Designers primarily develop and design educational content and curricula. Both roles often work remotely and serve similar industries, but their core responsibilities differ in focus and skill set.

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

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

What are popular job titles related to Remote Learning Enablement jobs in Chicago, IL?

For Remote Learning Enablement jobs in Chicago, IL, the most frequently searched job titles are:

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

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

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

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

Infographic showing various Remote Learning Enablement job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 77% Full Time, 21% Part Time, and 1% Contract. Highlights an 88% Physical, 2% Hybrid, and 10% Remote job distribution.

External Wholesaler, Annuity Distribution

Massachusetts Mutual Life Insurance Company (MassMutual)

Chicago, IL • On-site, Remote

Full-time

Re-posted 4 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 311 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.

What MassMutual employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom