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Insurance Sales Weekend Jobs in Boston, MA (NOW HIRING)

AAA Northeast

Insurance Sales Agent (59818)

Saugus, MA

$26 - $31.50/hr

Sell insurance products and services, meeting or exceeding sales goals * Interact with members in person at the branch, over the phone and online * Compile coverage and rating information; confirm ...

AAA Northeast

Insurance Sales Agent (58239)

Newton, MA

$27.25 - $30.15/mo

Sell insurance products and services, meeting or exceeding sales goals * Interact with members in person at the branch, over the phone and online * Compile coverage and rating information; confirm ...

Nexera

Entry Level Remote Insurance Sales

Boston, MA · Remote

$1.5K - $3.2K/wk

Access to 60+ insurance carriers -- independent model, never tied to one company * A step-by-step training system built specifically for new agents * Weekly pay on every closed sale Backgrounds that ...

Nexera

Entry Level Remote Insurance Sales

Boston, MA · Remote

$1.5K - $3.2K/wk

Access to 60+ insurance carriers -- independent model, never tied to one company * A step-by-step training system built specifically for new agents * Weekly pay on every closed sale Backgrounds that ...

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All JobsInsurance Sales JobsInsurance Sales Weekend JobsInsurance Sales Weekend Jobs in Boston, MA

Insurance Sales Weekend information

See Boston, MA salary details

$32K

$100.1K

$152.6K

How much do insurance sales weekend jobs pay per year?

As of Aug 20, 2026, the average yearly pay for insurance sales weekend in Boston, MA is $100,075.00, according to ZipRecruiter salary data. Most workers in this role earn between $74,400.00 and $126,000.00 per year, depending on experience, location, and employer.

What is an insurance sales weekend job?

Insurance Sales Weekend jobs involve selling insurance policies—such as auto, health, life, or home insurance—primarily during weekends. These roles may suit individuals seeking part-time or flexible work schedules, such as students or those supplementing existing income. Weekend insurance sales agents engage with potential clients, assess their insurance needs, explain policy options, and help customers choose the best coverage. The role often includes a mix of phone, online, and in-person interactions, and may involve meeting sales targets or earning commission.

What are the key skills and qualifications needed to thrive as an insurance sales professional working weekends?

To thrive as an Insurance Sales professional on weekends, you need strong sales abilities, knowledge of insurance products, and typically a state-specific insurance license. Familiarity with CRM software, online quoting tools, and digital communication platforms is often required. Excellent interpersonal skills, self-motivation, and the ability to build trust quickly help you stand out in this customer-facing role. These skills ensure you can effectively engage clients, close sales, and maintain compliance in a competitive, time-sensitive environment.

What are some common challenges faced by insurance sales professionals working on weekends, and how can they be addressed?

Insurance sales professionals working on weekends often face challenges such as reaching decision-makers who may be unavailable or less willing to discuss policies outside regular business hours. However, weekends can also provide opportunities to connect with clients who are too busy during the week. Successful agents typically adapt by being flexible with their scheduling, offering virtual consultations, and focusing on relationship-building. Proactive communication and clear follow-ups are key strategies to overcome these challenges and maximize weekend productivity.

What is the difference between Insurance Sales Weekend vs Insurance Agent?

AspectInsurance Sales WeekendInsurance Agent
CertificationsOften no formal certifications required, but some knowledge of insurance products helpsRequires state licensing and certifications to sell insurance
Work EnvironmentTemporary, event-based, often part-time or seasonalFull-time or part-time, office or client-facing settings
Employer & Industry UsageUsed by insurance companies for promotional or sales eventsEmployed directly by insurance companies or agencies to sell policies
Search & Comparison IntentPeople looking for short-term sales opportunities or event-based rolesIndividuals seeking ongoing sales careers in insurance

Insurance Sales Weekend roles are typically short-term, event-based sales opportunities that may not require formal licensing, whereas Insurance Agents are licensed professionals who sell insurance policies on a regular basis. The roles differ mainly in duration, certification requirements, and employment structure, with Insurance Agents pursuing continuous careers in the industry.

Can I do insurance sales as a side hustle?

Insurance sales can often be pursued as a side hustle, as many agents work part-time or freelance to supplement their income. Success typically requires obtaining relevant licenses, such as a state insurance license, and managing flexible schedules to accommodate client appointments outside of full-time work hours.

Why do most insurance sales weekend agents quit?

Most insurance sales weekend agents quit due to the challenging nature of the job, which often involves high rejection rates, inconsistent income, and the need for strong sales skills. The part-time schedule and pressure to meet sales targets can also lead to burnout and turnover.

What are the most commonly searched types of Insurance Sales jobs in Boston, MA?

The most popular types of Insurance Sales jobs in Boston, MA are:

Insurance Sales Weekend jobs near you

Insurance Sales Agent - Marlborough

First Technology Federal Credit Union

Marlborough, MA • Hybrid

$120K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 10 days ago

Job description

Description

The Insurance Sales Agent serves as the first contact with a prospective client, seeking to sell insurance products to protect members from financial loss.  This position also maintains relationships with existing policyholders, advising of changes in coverage, proactively contacting the client on renewal to discuss coverage and obtain expiration dates to quote other businesses while providing risk management advice. 

Here’s what you can expect from the job and what you need to be successful:   

What You'll Do:  

  • Respond to phone calls, emails, walk-ins and member referrals from credit union staff in a timely manner; answer member questions regarding insurance coverage and offer solutions with the members' best interest in mind
  • Develop and maintain strong relationships with stakeholders in the insurance department and the credit union
  • Prepare proposals for prospects and make follow-up calls to members; maintain up to date electronic files on all current and prospective members in compliance with agency and regulatory requirements
  • Maintain list of policy expiration dates to contact and provide proposals in the future
  • Maintain up-to-date electronic customer files in compliance with agency and regulatory requirements
  • Maintain up-to-date knowledge of insurance industry trends, products/services, procedures and policies

Essential Skills: 

  • Minimum Education: High School Diploma; Bachelor’s degree is preferred 
  • Minimum 2 years’ sales and customer service experience in the insurance industry, demonstrating a successful sales record
  • Skilled in organizing, analyzing and interpreting data to reach sound decisions and guide clients based on individual risk tolerances
  • Ability to work autonomously to manage time effectively and prioritize work appropriately to meet deadlines
  • Ability to establish and maintain strong relationships with internal stakeholders 
  • Proven track record as a insurance sales agent with an independent personal lines agency
  • Broad knowledge of the laws and regulations regarding personal lines insurance products
  • Familiarity with an agency management system (such as Hawksoft)
  • Working knowledge of Microsoft Office Suite and Comparative Rater
  • Certification/License: Property & Casualty license, Life Insurance license  

Location: Marlborough/Chelmsford, MA (HYBRID) 

Target Compensation: $34,800 annually + bi-weekly draw (draw is reconciled against future potential incentive earnings which could be up to $120K+ in the first year) 

Schedule: Monday – Friday | 8am-5pm

 #FTHP


Who We Are:
What makes First Tech different? Click here to learn more!
Every great journey begins with a bold idea—and ours is no different. First Tech and DCU were founded on the belief that financial solutions should put people first. That belief has fueled decades of innovation and service, rooted in the tech sector and expanding to support members from all walks of life.
Employees are eligible for:
• Traditional medical, dental, and vision coverage
• Generous 401(k) match
• Paid Time Off: You'll accrue up to 15 days in your first year. In addition, you'll receive 40 hours of sick time and 3 personal days, which refresh annually
• Paid federal holidays
• Special employee pricing on lending products such as mortgage, auto, and personal loans (eligibility subject to standard account requirements and underwriting criteria)
Employment Statements:
First Tech is an equal opportunity employer, and we value diversity, inclusion, and equity at our company. We evaluate qualified applicants without regard to race, color, religion, age, sex, sexual orientation, gender identity, national origin, disability, veteran status, and other legally protected characteristics.
If you're applying for a job and need a reasonable accommodation for any part of the employment process, please send an email to recruiters@firsttechfed.com and let us know the nature of your request and contact information. Please note that only those inquiries concerning a request for reasonable accommodation will be responded to from this email address.
First Tech is not currently offering Visa transfer/sponsorship for this position.

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