True North Group LLC.Verified Source

Direct Sales Representative, Insurance B2B

Onsite · Tampa, Florida
Posted August 12, 2026
payroll

Overview

True North Group seeks a Direct Sales Representative to own a territory in Tampa, Florida, selling insurance plans to small and medium businesses. You'll build relationships with business owners, present to groups of 50-100 employees, and use Salesforce CRM to manage your pipeline. This role offers flexible scheduling, weekly draws, commissions, and career growth. You'll become a trusted advisor, supporting clients through claims and renewals.

What You'll Do9

  • 1Build relationships with business owners and key decision-makers through in-person visits and phone calls.
  • 2Present insurance products to groups of 50-100 employees, using Salesforce CRM to track leads and follow-ups.
  • 3Set up meetings to review client needs and recommend suitable Health & Life insurance plans.
  • 4Develop and maintain your own client list through referrals and cold calling in your territory.
  • 5Follow up on leads and conduct daily sales activities, reporting progress to your manager.
  • 6Collaborate with your manager to set monthly and quarterly sales goals.
  • 7Provide ongoing support to clients, answering questions and assisting with claims.
  • 8Maintain accurate records in Salesforce CRM, ensuring timely follow-up on all inquiries.
  • 9Attend team meetings and training sessions to enhance product knowledge and sales skills.

Requirements8

  • 1Health & Life general lines license, or ability to obtain within 90 days (company assists with costs).
  • 2Bachelor's degree or 4+ years of work experience; equivalent experience in outside sales considered.
  • 31-3 years of sales or customer service experience, preferably in outside sales.
  • 4Strong teaching ability, both in-person and online, to educate clients and groups.
  • 5Excellent organizational and communication skills for managing multiple accounts.
  • 6Proven ability to build and maintain client relationships.
  • 7Willingness to work flexible hours, including evenings and weekends, to meet client needs.
  • 8Valid driver's license and reliable transportation for local travel.

Salary Insight

Salary not disclosed in listing

Location

Typeonsite
LocationTampa, Florida

Required Skills

salesforcecrminsuranceoutside-salesb2b
Share:

Similar open positions

Explore active roles that match your skills and interests.

True North Group LLC.

8h agoPhoenix, Arizonapayroll

Direct Sales Representative, Insurance B2B

You will own a territory in Phoenix, building relationships with small and medium business owners to sell Health & Life insurance plans. You'll join a supportive team at True North Group, working both in-person and via phone with Salesforce CRM to manage your pipeline. This role offers flexible scheduling and uncapped earning potential through bonuses and commissions.

Competitive salary
salesforcehealth insurancelife insurance+2 more

True North Group LLC.

8h agoDallas, Texaspayroll

Direct Sales Representative, Insurance B2B

True North Group seeks a Direct Sales Representative to own B2B insurance sales in the Dallas territory. You will build relationships with business owners, present to groups of 50-100 employees, and manage a client pipeline using Salesforce CRM. You will have autonomy to set your schedule, with training provided. This role offers uncapped commission, quarterly incentives, and career growth.

Competitive salary
salesforceb2b salesclient relationship management+2 more

Alpine Legacy Group

14h agoTampa, Floridapayroll

Direct Sales Representative, Insurance & Territory Management

You will own a local territory in Tampa, selling supplemental insurance programs directly to business owners and families, with uncapped earning potential from week one. You will join a fast-growing team that values discipline, grit, and ownership, backed by hands-on training and mentorship. This role offers a path to leadership and long-term renewal income, with promotions based solely on performance. You will close deals from first handshake to lifelong client, supported by a winning culture and real accountability.

74K–92K
CRMRelationship BuildingNetworking+4 more

True North Group LLC.

8h agoPortland, Oregonpayroll

Outside Sales Representative, Insurance - True North Group

You will own a Portland territory, visiting local businesses to sell supplemental insurance and build long-term client relationships. You will manage your own schedule, balance field visits with phone outreach, and track all activity in Salesforce. You will join a supportive team of 10 reps, backed by weekly training and strategy sessions. This role offers uncapped commissions, quarterly retreats, and lifetime-vested renewal income. You will be a trusted advisor to small and mid-sized businesses, protecting their people with Health & Life coverage.

Competitive salary
salesforceprospectingpresentations+2 more

Summit Business Group

9h agoPhoenix, Arizonapayroll

Insurance Sales Representative, Supplemental Benefits

You own your territory as a Direct Insurance Sales Representative, connecting with small and medium-sized businesses to offer supplemental benefits plans. You manage your schedule, drive sales, and build lasting relationships with clients. You rely on Salesforce CRM to track leads and close deals. Your assertive communication and follow-through turn prospects into loyal clients. This role rewards self-starters with uncapped commission and advancement opportunities.

Competitive salary
salesforcecold callingoutside sales+1 more

R.I.S.E. Financial

8h agoLas Vegas, Nevadapayroll

B2B Sales Representative, Insurance & Client Growth

Own your sales territory from day one, connecting with local business owners to offer supplemental insurance products. You’ll build your own client base, negotiate contracts, and close deals with full autonomy. The team supports you with paid training, mentorship, and a weekly draw option to ensure stability while you grow. This role rewards relentless effort with uncapped commissions, cash bonuses, and stock options—plus the freedom to define your schedule. If you thrive on direct client interaction and want to control your earnings, this is your launchpad.

65K–85K
lead generationrelationship buildingnegotiation+2 more