Entry Level Digital Jobs in Portland, OR (NOW HIRING)

Join Our Team at True North Group

Position Title: Entry-Level Sales Representative

Open Role: 1 Territory, Outside Sales Opportunity

About Us:

True North Group isn't just another insurance agency; We prioritize genuine relationships, outstanding service, and a positive work environment on a mission to protect small and mid-sized businesses and their employees. If you're eager to jumpstart a career where you can learn, grow, and make a difference, read on.

The Role:

As our newest Entry-Level Sales Representative, you'll be the face of True North in your assigned territory. You'll set your own appointments and craft a schedule that fits the rhythms of the local business community. Every day you'll:

Engage with Business Owners: Visit storefronts, offices, and industrial parks to connect with decision-makers. Your goal is to understand their needs and introduce them to insurance solutions that protect their teams.

Deliver Informative Presentations: Lead open-forum sessions for employee groups (anywhere from 15 to 75 people), explaining benefit packages in an easy-to-understand way.

Provide Ongoing Support: From answering questions about coverage details to guiding clients through a claim, you'll become a trusted advisor who businesses rely on.

Leverage Technology: Use Salesforce CRM to log client interactions, track follow-ups, and manage your pipeline—keeping everything organized and efficient.

Prospect and Grow: Cold-call new prospects, follow up on leads, and ask satisfied customers for referrals. You'll be proactive, resourceful, and ready to explore every avenue to expand your book of business.

Report and Collaborate: Share your weekly activity reports—calls made, meetings held, policies quoted—with your manager during team huddles. Your insights help us all improve.

What we look for:

Hungry to Learn: You might be new to sales, and that's perfectly fine. We'll train you from the ground up, so any drive to learn quickly will serve you well.

People Person: You genuinely enjoy talking to others, asking questions, and listening carefully. Whether chatting one-on-one or speaking in front of a group, you communicate clearly and confidently.

Organized & Self-Driven: Managing your own schedule in the field means you need strong organizational skills and a "get-it-done" mindset.

Service-Oriented: You take pride in making others feel cared for. When a client has a concern or question, you're the one they trust to find answers.

License-Ready: You either hold a Health & Life general lines license or are willing to get it within 90 days. Licensing reimbursement available. 

What We Offer You

Hands-On Training: We combine virtual classrooms with in-field shadowing to teach you everything—from product knowledge to presentation best practices.

Weekly Draw Pay: A guaranteed base while you build your territory, plus immediate eligibility for bonuses and commissions.

Exciting Incentives: Quarterly incentive retreats, annual trips, cash bonuses, stock awards, and lifelong renewal commissions once you qualify.

Climb the Ladder: Proven career paths await—whether you aspire to become a team leader, a field coach, or advance into agency management.

Continuous Development: Regular coaching sessions, sales workshops, and leadership training help you stay sharp and elevate your game.

Flexible Hours: As your client list grows, you'll have more control over your day. Work when local businesses are open and still enjoy evenings or weekends off.

Additional Qualifications

Education or Experience: A bachelor's degree is a plus, but if you've spent at least four years in a customer-facing environment (retail, hospitality, another sales role), we want to hear from you. Recent graduates are encouraged to apply.

Tech Comfort: You're comfortable learning new software—Salesforce and other digital tools come naturally to you.

Motivation & Grit: You're coachable and thrive in a self-directed environment. Building a territory from scratch isn't easy, but the rewards are well worth it.

Licensing Commitment: If you're not already licensed in Health & Life general lines, you commit to obtaining that license within three months. We take care of tuition and exam fees.

How to Get Started

Join True North Group, where you'll receive unwavering support, top-tier training, and the chance to build a career you can be proud of. If you're ready to roll up your sleeves, learn the ropes, and make a tangible difference in your community, this is your opportunity.

https://www.thetruenorthgroupllc.com

We can't wait to see what you bring to the team!