Jobs in Kentucky 2026 (Now Hiring) - Smart Auto Apply

Altitude is searching for resilient individuals who thrive under pressure.

In the world of sales, resilience is not just an assetit's a necessity. At Altitude, we recognize that success comes to those who are unafraid to push through the tough times and come out stronger on the other side. We're looking for individuals who embody this spirit, who understand that every "no" brings them one step closer to a "yes," and who approach challenges with an unshakeable determination.

If you're someone who refuses to let obstacles stand in your way, who sees each setback as a setup for a comeback, and who is fueled by the drive to turn adversity into achievement, then you'll find your home at Altitude. Our Entry Level Territory Sales Associates are the backbone of our success, and we're committed to providing an environment where your resilience will be rewarded with tangible results, growth opportunities, and a clear path to career advancement.

Position Overview:

As an Entry Level Territory Sales Associate at Altitude, you will be the catalyst for our growth and success in the marketplace. Your day-to-day will involve independently managing a designated sales territory, where you will be responsible for building and nurturing relationships with small to medium-sized businesses. Cold calling will be your primary tool, and your ability to remain undeterred in the face of rejection will be key to your success.

Your role will include:

• Prospecting: Identifying and reaching out to potential clients within your territory, utilizing cold calls, networking, and innovative lead generation techniques.

• Relationship Building: Engaging with business owners and decision-makers, understanding their needs, and presenting Altitude's insurance solutions in a way that resonates with them.

• Closing Sales: Leveraging your resilience and persuasive skills to close deals, often on the spot, and ensuring that each client fully understands the value we bring.

• Follow-ups: Scheduling and executing follow-up meetings to solidify client relationships and secure long-term commitments.

• Continuous Learning: Adapting to client feedback, market trends, and new sales strategies to consistently improve your performance.

At Altitude, we believe that the best salespeople are those who can weather the storm and keep moving forward with confidence. If you are resilient, resourceful, and ready to make a significant impact, we encourage you to apply.

Overview of Duties and Responsibilities:

This is an outside sales position working in your own assigned sales territory. We will train you to call on small and medium-sized businesses that operate in a variety of industries, meeting face-to-face with business owners and decision-makers to offer some of the industry's best supplemental insurance products and services to them and their employees. You will work with business owners, benefits managers, and their employees individually at times; other times, you will give product presentations with employee groups as large as 50-100+ people. You will be expected to:

• Respond to general emails and phone calls from clients

• Set follow-up appointments with prospective and current clients to review their needs

• Be present on scheduled calls or meetings with your sales team or manager

• Call on new businesses, referrals, and existing clients who need to be reserviced

• Build and maintain your own book of business

• Meet with sales team manager as needed to discuss and set your upcoming monthly and quarterly target sales goals and quotas

• Develop relationships with local business owners in your territory

• Set your own scheduled working hours and submit them to your sales manager each week

• Follow up on provided sales leads and cold-call on businesses in person, balancing "cold" lead generation and sales with your warm leads and appointments with existing clients

• Submit your sales metrics and activity daily

We Offer:

• Virtual classroom training as well as hands-on sales training in your own territory

• Weekly draw pay with bonuses and commission eligibility upon start

• Quarterly and annual incentive trips, cash bonuses, and stock share bonuses

• Advancement and promotions based on personal performance

• Excellent ongoing professional development, advanced sales training, and leadership training

• Increased schedule flexibility once you have an established book of business

• Work around other like-minded, driven, caring people in a culture that feels like a family

Additional Position Qualifications:

• Already licensed in Health & Life general lines (or willing and able to obtain Health & Life producer license - licensing reimbursement offered)

• Bachelor's degree or a minimum of 4 years of professional (post-high school) work experience. Candidates within 6 months or less of degree completion will be considered, as will candidates with less than 4 years of professional work experience with relevant or specialized outside sales experience.

We do not use AI in our recruiting/interview process. Your resume will be reviewed and your interview will be conducted by one of our team members. Due to the nature of this position talking to others about insurance during difficult health topics we strongly believe this position cannot lean on AI but rather requires connecting with people.