Direct Outside Sales Leader

Summit Business Group; Cheyenne (WY); On-site; USD 100,000 - 140,000; Full time

Benefits offered by this job

Virtual classroom training

Draw pay + bonuses

Incentive trips

Professional development

Flexible schedule

Team-focused culture

Job summary

Summit Business Group seeks a Direct Outside Sales Leader to guide a growing sales team and expand our supplemental insurance offerings to small and medium-sized businesses. You will train, mentor, and build your own client portfolio while applying our proven sales strategies in the field.

You’ll leverage Salesforce to engage prospects, balance cold outreach with warm leads, and report progress weekly. A Bachelor’s degree or 10+ years in sales is expected, with Health & Life licensing support

Qualifications

• 10+ years of outside or customer-facing sales experience, preferably in insurance or related field.
• Ability to train others in-person and online.
• Excellent organizational, communication, and presentation skills.
• Licensed in Health & Life general lines or willingness to obtain within 90 days.

Responsibilities

• Respond promptly to client emails and phone calls.
• Schedule follow-up appointments to assess evolving needs.
• Participate in scheduled calls or meetings with sales team or manager.
• Prospect new businesses, referrals, and existing clients for continued service.
• Build and maintain a robust book of business through proactive relationship development.
• Collaborate with your sales team manager to establish and achieve monthly and quarterly targets.
• Cultivate relationships with local business owners within your territory.
• Set your own working hours and provide weekly schedules to your sales manager.
• Balance cold lead generation with warm leads using provided leads and targeted calls.
• Submit daily sales metrics and activity reports.

Skills

Sales leadership

Training delivery

Communication skills

Relationship building

Self-management

Education

Bachelor's degree

Tools

Salesforce

Job description

Join Our GrowingTeam at Summit Business Group

Position: Direct Outside Sales Leader

About Us: At Summit Business Group, we're more than just an insurance agency—we're a supportive family dedicated to providing exceptional supplemental benefits plans to small and medium-sized businesses and their employees. Our culture focuses on building authentic connections and offering compassionate support to everyone we serve. If you're passionate about making a meaningful impact on others' lives, our Direct Outside Sales Leader role could be the perfect fit for you!

The Role: As a Direct Outside Sales Leader, you'll have the exciting opportunity to inspire and guide a team while quickly advancing your career. You'll leverage your sales experience to implement our proven sales strategies and ensure seamless execution in the field. In your first 90 days, you'll transition into a leadership role where you can train and mentor new team members while also building and managing your own client portfolio.

Enjoy the flexibility of setting your own schedule, tailoring your hours to meet your clients' needs. Your primary focus will be on developing strong, lasting relationships with business owners and essential clients. By understanding their unique challenges, you'll present tailored insurance solutions that genuinely enhance their operations.

Using our cutting-edge Salesforce CRM, you'll engage potential clients through a mix of cold calls and in-person meetings. Your aim isn't just to close sales; it's to become a trusted advisor, providing ongoing support and guidance—especially during the claims process—to ensure client satisfaction and foster long-term relationships.

What We're Looking For:

• A minimum of 10 years of sales experience, ideally in customer-facing or outside sales roles.

• Proven ability to conduct effective training sessions, both in-person and online.

• Excellent organizational, communication, and presentation skills.

• A genuine passion for helping and empowering clients, with a strong commitment to their well-being.

• Health & Life general lines license, or a willingness to obtain one within 90 days (we'll support you through the process).

Position Overview:

This is a leadership role in outside sales, operating within your designated territory. You'll receive extensive training to engage with small and medium-sized businesses across various industries, interfacing directly with business owners and decision-makers to offer industry-leading supplemental insurance products and services. Your responsibilities will include:

• Responding promptly to client emails and phone calls.

• Scheduling follow-up appointments with prospective and current clients to assess their evolving needs.

• Participating in scheduled calls or meetings with your sales team or manager.

• Prospecting new businesses, referrals, and existing clients for continued service.

• Building and maintaining a robust book of business through proactive relationship development.

• Collaborating with your sales team manager to establish and achieve monthly and quarterly sales targets and quotas.

• Cultivating meaningful relationships with local business owners within your territory. Selling Business to business.

• Setting your own working hours and providing weekly schedules to your sales manager.

• Balancing cold lead generation and sales with warm leads and appointments with existing clients, leveraging provided sales leads and engaging in targeted cold-calling efforts.

• Submitting daily sales metrics and activity reports to track progress and performance.

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, stock share bonuses, and lifetime-vested renewal commissions

• 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 10 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 10 years of professional work experience who have relevant or specialized outside sales experience.

Your New Journey: If you are looking to make a meaningful impact in your career, consider joining Summit Business Group. Here, your compassionate spirit and dedication to service can lead to a fulfilling career. We're excited to redefine what it means to be in insurance sales with a team that values integrity, compassion, and the well-being of its members.