Outside Sales Representative, B2B Insurance Sales Trainer
Overview
You will own B2B field sales and training for Divinity Group, driving $75K-$95K in annual earnings. You will sell supplemental insurance to business owners while coaching new reps through hands-on field training. This role combines personal production with leadership development. You will operate remotely, manage your own schedule, and build trust through integrity. You will thrive in a structured environment that rewards discipline and execution.
What You'll Do8
- 1Execute face-to-face B2B sales calls with business owners, presenting supplemental insurance solutions and closing deals.
- 2Follow a structured sales process to meet weekly performance metrics and track outcomes in CRM.
- 3Train and mentor new sales representatives through field-based coaching, modeling professional conduct and sales technique.
- 4Build long-term client relationships through consistent follow-up and account management, ensuring high retention.
- 5Prepare and deliver sales presentations to decision-makers, tailoring benefits to each business's needs.
- 6Maintain accurate records of sales activities and pipeline in Salesforce or equivalent, reporting weekly to leadership.
- 7Support team readiness by leading training sessions and providing feedback on sales calls and performance.
- 8Drive continuous improvement by sharing best practices and contributing to the sales playbook.
Requirements8
- 13-5 years of B2B sales experience with proven results in a structured, high-accountability environment.
- 2Experience in training or leadership roles, mentoring others to meet sales targets.
- 3Strong communication and interpersonal skills, with the ability to build trust quickly.
- 4Self-motivated and dependable, able to work independently while following established systems.
- 5Comfortable with field-based work, including travel within the local community.
- 6Ability to perform in goal-driven conditions and adapt to changing priorities.
- 7Valid driver's license and reliable transportation for client meetings.
- 8Insurance licensing is a plus; company will assist with licensing and reimbursement.
Salary Insight
$75 - $95k per year
Location
Required Skills
Similar open positions
Explore active roles that match your skills and interests.
Canyon Creek Financial LLC.
VerifiedOutside Sales Representative & Trainer, B2B Insurance
You'll own a local B2B sales territory for Canyon Creek Financial, selling supplemental insurance to business owners while training and mentoring new agents. Your work directly drives revenue and shapes the team's growth, with a weekly base draw plus uncapped commissions. You'll operate as an independent contractor with support from a collaborative team, covering licensing costs after you hit targets. This role stands out for its dual focus: you close deals and build future sales talent, with a clear path to leadership.
True North Group LLC.
VerifiedOutside Sales Representative & Trainer, Insurance Benefits
The Outside Sales Representative and Trainer owns a local territory, selling supplemental insurance to small and mid-sized businesses while training new agents. You build your own book of business and mentor others, leading from the front. This hybrid role combines field sales with hands-on coaching. You work with business owners, deliver group presentations, and guide reps through call reviews and prep sessions. What sets this apart: dual focus on personal quota and team development, with clear paths into senior leadership.
Divinity Group LLC
VerifiedEntry-Level Outside Sales Representative
Entry-Level Outside Sales Representative at The Divinity Group owns B2B supplemental insurance sales across a designated territory. This field-based role blends remote flexibility with in-person client meetings to protect employees through business-sponsored policies. The team values purpose-driven action, pairing a first-responder mindset with a supportive culture. With uncapped commissions and an optional base draw, this position rewards performance while offering mentorship and training to build a sales career.
Allegiant Business Group
VerifiedSales Representative and Field Trainer, B2B Supplemental Insurance
You will lead by example as a Sales Representative and Field Trainer in Dallas, Texas, building your own book of business while mentoring newer agents. In the first 90 days, you will conduct face-to-face presentations with small and mid-sized businesses, recommend supplemental insurance solutions, and coach agents in the field. You will work with a collaborative team that values discipline, integrity, and consistent growth, supported by structured onboarding and leadership development. This role stands out because you will balance personal production with developing others, earning uncapped income through commission and bonuses, with a clear path to higher leadership roles.
Devine Business Group
VerifiedSales Representative and Trainer, B2B Insurance
You will own inside and outside sales for Devine Business Group, bringing supplemental insurance products to businesses across the Seattle area and mentoring a growing team of sales reps. Working as an independent contractor, you will balance personal sales goals with coaching and training to build a high-performance culture. This role combines direct B2B sales with hands-on mentorship, offering a base draw and uncapped commission. You will thrive here if you are goal-driven and enjoy helping others succeed.
Devine Business Group
VerifiedSales Representative & Trainer, B2B Insurance
You will own field sales and mentor a growing team at Devine Business Group, driving B2B supplemental insurance growth in the Portland area. As an independent contractor, you manage your own schedule and balance personal sales goals with coaching new reps. You work directly with business decision-makers to design customized insurance solutions, using CRM systems and Mac tools to track progress. This role stands out through its dual focus on sales and training, with uncapped commission and licensing support.