Top 69 Inside sales representative Jobs in Pittsfield, Ma

Medicare Sales Independent Contractor (1099) - Remote
MyPlanAdvocate —Massachusetts
- $65,000 - $85,000 a year
- Contract
- Remote
- Mid-level
1d
Vice President, Strategic Sales - East (Remote)
CrowdStrike —Massachusetts
- $200,000 - $340,000 a year
- Full-time
- Remote
- 5 years
- Travel
- Recruiting
- Paid holidays
- Parental leave
Remote Independent Medicare Sales Agent (1099)
MyPlanAdvocate —Massachusetts
- $65,000 - $85,000 a year
- Contract
- Remote
- Mid-level
1d
Remote Medicare Sales Agent - Independent Contractor (1099)
MyPlanAdvocate —Massachusetts
- $65,000 - $85,000 a year
- Contract
- Remote
- Mid-level
1d
Beauty Advisor (Inside Sales) Sally Beauty 10268
Sally Beauty Holdings —Pittsfield, MA
- $15.00 - $17.10 an hour
- US work authorization
- Ability to lift 25 pounds
- Entry level
- Health insurance
- Dental insurance
Inside Sales
Granite Group —Great Barrington, MA
- $20 - $25 an hour
- Entry level
- Paid holidays
- Health insurance
Quick Apply
Proven Inside Sales Representative – Remote, K-12 Sales Required
Junior Library Guild —United States
- $48,000 - $150,000 a year
- 8 hour shift
- Remote
- Mid-level
- In-person
- 2 years
- Paid holidays
- Health insurance
Quick Apply
Remote Licensed Insurance Sales Representative
Brittanny Perry Allstate —United States
- $50,000 - $100,000 a year
- Full-time
- Remote
- Mid-level
- Business development
- 2 years
- Paid training
- Paid holidays
Quick Apply
5d

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Professionalism — reliable transportation, a valid driver’s license, and proof of insurance required. Do you have a valid driver's license and vehicle insurance…
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Inside Sales Representative - B2B
The Kingswood Company —Columbus, OH
Complete outbound and inbound sales calls as assigned and directed, and in accordance with established activity goals, and account cultivation and development…
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Inside Sales/Estimator
The Habegger Corporation —Columbus, OH
This includes partnering on sales calls when appropriate. Answer customer calls and provide a high level of customer service.
$65,000 - $80,000 a year
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inside sales representative jobs near pittsfield, ma

Medicare Sales Independent Contractor (1099) - Remote

MyPlanAdvocate -
Massachusetts

Apply Now

Job Details

Contract
$65,000 - $85,000 a year
1 day ago

Qualifications

Medicare
Health insurance
Health insurance sales
Insurance sales
Health Insurance License

Full Job Description

MPA | Independent Medicare Sales Agent

Licensed Medicare Agents Only - active Health Insurance License is Required

MPA is a leading Medicare agency in the United States, committed to staying on the cutting edge of technology and creating exceptional experiences for both customers and agents. We believe that happy customers begin with fulfilled professionals, which is why we've designed a flexible, rewarding opportunity for experienced Medicare sales agents looking for independence and growth.

The Opportunity

As an independent Medicare Sales Agent with MPA, you'll enjoy the freedom of a 1099 contractor role while gaining access to premium tools, warm leads, and operational support that set you up for success. If you're tired of rigid corporate environments with forced overtime, inflexible schedules, and unattainable goals, this opportunity offers the perfect alternative.

This isn't your average agency gig-we're investing heavily in growth, and agents who join now will be first in line to shape the future of how we sell Medicare.

Why Timing Matters

Carrier release deadlines are quickly approaching. Agents who onboard now will be ready to sell by September 1, positioning themselves to maximize earnings during the most lucrative part of the Medicare calendar: AEP and OEP.

We're actively investing in lead generation, advertising, and tech infrastructure. Our leadership team is laser-focused on agent success-and urgency is high. Don't miss your window.

What Sets Us Apart

Complete Flexibility: No minimum hours requirement-work when and where you want
Quality Leads: Free, inbound warm transfers after Medicare A&B, zip code, and Medicaid status verification
Modern Technology: AI-enabled platform to streamline your workflow and eliminate busywork
Attractive Compensation: Competitive commission structure with weekly direct deposit
Seasonal or Year-Round: Ideal for agents focused on AEP/OEP or those looking for long-term growth

Why Join Now?

Agents who come on board today will be fully ramped ahead of the September carrier release deadline. By joining MPA now, you'll gain a critical head start for AEP/OEP and position yourself for your most successful season yet-all while maintaining the freedom and flexibility of independent work.

Ideal Candidates

Experienced or newer Medicare agents looking for greater independence
High-performers tired of chasing low-quality leads
Professionals seeking a better work-life balance without sacrificing income

Must Have:

Active Health Insurance License for Your Resident State
2026 AHIP Certification

Ability to Obtain During Onboarding:

Errors & Omission Insurance
Additional Non-Resident State Licenses

Next Steps

Ready to break free from the traditional employment model while still having access to elite support and resources? Join MPA's team of independent contractors and experience the perfect balance of freedom and opportunity.

MPA is proud to be building a better way to meet the needs of everyone we serve-including our valued sales professionals.

Apply Now

Refine Your Search

inside sales representative jobs in pittsfield, ma

Medicare Sales Independent Contractor (1099) - Remote

Vice President, Strategic Sales - East (Remote)

Remote Independent Medicare Sales Agent (1099)

Remote Medicare Sales Agent - Independent Contractor (1099)

Beauty Advisor (Inside Sales) Sally Beauty 10268

Inside Sales

Proven Inside Sales Representative – Remote, K-12 Sales Required

Remote Licensed Insurance Sales Representative

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