Account Executive-Massachusetts Captive Territory

sentryinsurance; Boston (MA); Hybrid; USD 198,000 - 234,000; Full time

Benefits offered by this job

Home office setup

Company car + travel in territory

Sentry University training

Tuition reimbursement

Comprehensive benefits

401(k) match 8%

Job summary

Sentry Insurance is seeking an Account Executive to drive direct sales of niche commercial insurance products and related offerings. You’ll build durable client relationships, coordinate with underwriting and service teams, and expand premium volume within a defined Massachusetts territory.

The role emphasizes travel within the territory, strong licensing requirements, and a performance-based compensation plan with substantial incentive opportunities.

Qualifications

• Bachelor's degree or equivalent work experience in sales
• Ability to obtain P&C and Life licenses to sell Sentry products
• Self-discipline and ability to thrive in a remote work environment
• Strong multitasking, prioritization, communication, and organization
• Strong analytical and math skills
• Valid driver's license with acceptable MVR and travel requirements

Responsibilities

• Sell directly to niche market accounts to increase premium volume
• Retain profitable business by providing effective service to policyholders
• Build and maintain quality relationships with businesses
• Collaborate with Underwriting, Claims, Loss Control, Audit, Customer Service and other key partners
• Call on and pursue niche market opportunities in territory
• Leverage existing customers for new growth and sales opportunities

Skills

Analytical skills

Communication

Sales experience

Remote work adaptability

Education

Bachelor's degree

Job description

Our highly trained Account Executives present specialized commercial insurance, 401K, and life insurance products that are perfectly designed for the industries we serve.

You're not just in it to win it. You want to crush it every time. Because that's what our sales professionals do. Not just anyone has what it takes to build strong and profitable relationships. If you're a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales.

We provide everything you need to carve out a sales career filled with success and purpose, including:

• High earning potential with base salary, commissions, monthly/annual incentives, plus recognition trips
• Outstanding benefits and a 401(k)-program matching dollar for dollar up to 8%
• Opportunities for professional development and growth
• Outstanding training and support
• An industry-leading line of products and services

Total currently estimated projected compensation range for this position is $197,561-$233,561, which is a combination of base pay, currently projected renewal commissions, and currently estimated new business commission opportunities. Commission opportunities - both renewal and new business -- are based on achievement of sales objectives and compliance with the terms of the applicable incentive plan.

The Massachusetts territory includes the following counties: Barnstable, Bristol, Dukes, Middlesex, Nantucket, Newport, Norfolk, Plymouth, and Suffolk. Residence within the sales territory is required.

What You'll Do

• Sell directly to niche market accounts to increase premium volume
• Retain profitable business by providing effective, quality service to policyholders
• Build and maintain quality relationships with businesses
• Work directly with Underwriting, Claims, Loss Control, Audit, Customer Service, and other key partners
• Call on and pursue all niche market opportunities assigned to your geographic territory
• Leverage current customers and relationships for new growth and sales opportunities

What it Takes

• Bachelor's degree or equivalent work experience/related sales experience
• The ability to obtain and maintain the necessary P&C, and Life licenses required to sell the products Sentry offers
• Self-discipline and ability to thrive in a remote work environment
• Ability to multitask, prioritize, communicate effectively, and remain organized
• Strong analytical and math skills
• Acceptable Motor Vehicle Record with a valid driver's license and ability to meet travel requirements

Here is what you can look forward to as part of our team:

At Sentry, your total rewards go beyond competitive compensation. We're committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.

• Home Office: Enjoy the best of both worlds. With a home office set up and time in the field, with regular travel in your company car in your defined territory. We provide the cutting edge proprietary technology and tools you need to be more efficient and effective in the field including a laptop and cell phone reimbursement.
• Continuous Learning: Unlock your potential through Sentry University, including comprehensive, ongoing training, including licensure and take advantage of our tuition reimbursement program.
• Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.
• Investing in Your Future: We offer 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
• Giving Back: Through the Sentry Foundation, we're proud to support the United Way and make a difference in our communities.

Why Join Sentry?

At Sentry, we believe our people are the heart of our success. We're proud to be recognized for the culture we've built, earning spots on Forbes' lists for America's Best Midsize Employers and Best Employers for New Grads, as well as Newsweek's America's Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.

Building on a Legacy

Our future is bright, but it's anchored in a long history of stability. Since our founding in 1904, we've dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We're proud to have maintained an A+ rating from A.M. Best, the industry's leading authority, for over 30 years.

Your Career, Our Community

Whether you're working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you'll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoin