East Coast-based Advertising Sales Representative

Insurance Journal; New York (NY, PA); Remote; USD 73,000 - 120,000; Full time

Benefits offered by this job

401(k)

Dental insurance

Flexible schedule

Health insurance

Health savings account

Life insurance

Retirement plan

Vision insurance

Job summary

Wells Media Group, Inc. is seeking a motivated sales professional to manage an established, revenue-generating territory with NY, PA, CT and the UK.

This remote, full-time role offers uncapped commissions and a portfolio of existing advertisers to nurture from day one. You will drive outbound prospecting via email, LinkedIn and phone, renew and upsell, and work with a collaborative team representing Insurance Journal and other brands.

Qualifications

• 5+ years in outbound sales, preferably in B2B digital media.
• Track record of hitting activity or meeting-set goals.
• Experience originating and closing deals.
• Self-starter, independently motivated, and creative in finding new angles to win deals.
• Resourceful self-learner and creative thinker who tests approaches.
• Excellent written and verbal communication skills.
• Highly organized with strong follow-through.
• Comfortable working remotely and cross-functionally.
• Curious, coachable, and eager to learn a complex industry.

Responsibilities

• Represent Wells Media Group's portfolio with confidence, tailoring value propositions to each prospect's business goals.
• Drive outbound prospecting through email, LinkedIn, and phone outreach.
• Book and close qualified opportunities.
• Navigate objections and guide prospects through the decision process.
• Build strong relationships with decision-makers across the insurance ecosystem.
• Renew and upsell an established book of business.
• Track activity and pipeline in CRM.
• Keep leadership informed on outreach performance and market feedback.
• Participate in select industry trade shows and customer events.

Skills

Outbound sales

B2B sales

Communication

Relationship building

Negotiation

Remote work

Tools

CRM software

LinkedIn Sales Navigator

Job description

Remote | Full-Time | Uncapped Commission | Comprehensive Benefits

Wells Media Group, Inc. is a leading B2B media company serving the property & casualty insurance industry through trusted brands including Insurance Journal, Carrier Management, Claims Journal, and MyNewMarkets.com - reaching the largest insurance audience in the U.S.

We offer a competitive compensation and benefits package including medical, dental, vision, life insurance, a 401(k), & an employee stock ownership plan (ESOP).

Why This Role Is Exciting

You’ll be managing an established $1 million+ territory with significant opportunity to grow.

Due to the retirement of a longtime sales representative, Wells Media Group is offering a rare opportunity to take over an established, revenue-producing territory primarily serving New York, Pennsylvania, Connecticut, and the UK.

Unlike traditional commission-based sales positions that require building a territory from the ground up, this role comes with an existing portfolio of advertisers, established client relationships, and a strong foundation for continued growth.

Compensation is 100% commission-based, with uncapped commission and an established book of business from day one. You’ll have the opportunity to earn commissions through client renewals, account expansion, and new business development, backed by the resources, reputation, and support of a leading B2B media company.

You’ll join a collaborative team of experienced media sales professionals representing four trusted brands, with the tools, industry expertise, and support to help you succeed.

The property and casualty insurance industry is a cornerstone of the economy and a surprisingly fascinating and exciting business.

If you’re a motivated, relationship-driven sales professional who values autonomy, enjoys consultative selling, and wants to directly benefit from your success, this could be an exceptional next step in your career.

What You’ll Do

• Represent Wells Media Group's portfolio with confidence, tailoring value propositions to each prospect's business goals.
• Drive outbound prospecting through email, LinkedIn, and phone outreach.
• Book and close qualified opportunities.
• Navigate objections and guide prospects through the decision process.
• Build strong relationships with decision-makers across the insurance ecosystem.
• Renew and upsell an established book of business.
• Track activity and pipeline in CRM.
• Keep leadership informed on outreach performance and market feedback.
• Participate in select industry trade shows and customer events.

What We’re Looking For

• 5+ years in outbound sales - preferably in B2B environments with a focus on digital media.
• A track record of hitting activity or meeting-set goals.
• Experience both originating and closing deals.
• Self-starter, independently motivated, and creative in finding new angles to win deals.
• Resourceful self-learner and creative thinker who brings ideas, tests approaches, and continuously improves.
• Excellent written and verbal communication skills.
• Highly organized with strong follow-through.
• Comfortable working remotely and cross-functionally.
• Curious, coachable, and excited to learn a complex industry.

Bonus points: Experience selling SaaS, sponsorships, and/or familiarity with insurance, Insurtech, or risk management.

Deadline to apply is November 13, 2026

Pay: $73,100.00 - $120,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Flexible schedule
• Health insurance
• Health savings account
• Life insurance
• Retirement plan
• Vision insurance