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Insurance Sales Weekend Jobs in Portland, OR (NOW HIRING)

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Summit Insurance is seeking motivated, results-driven Insurance Sales Professionals who are licensed in Property & Casualty and Life & Health insurance and passionate about helping clients protect ...

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... Weekends Off Pathway to Leadership Requirements * Sales, customer service, or leadership experience preferred * Strong interest in building a career in the insurance industry is required

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... Weekends Off Pathway to Leadership Requirements * Sales, customer service, or leadership experience preferred * Strong interest in building a career in the insurance industry is required

Showing results 21-40

Insurance Sales Weekend information

See Portland, OR salary details

$31.3K

$97.7K

$149K

How much do insurance sales weekend jobs pay per year?

As of Aug 11, 2026, the average yearly pay for insurance sales weekend in Portland, OR is $97,690.00, according to ZipRecruiter salary data. Most workers in this role earn between $72,600.00 and $123,000.00 per year, depending on experience, location, and employer.

What are some common challenges faced by insurance sales professionals working on weekends, and how can they be addressed?

Insurance sales professionals working on weekends often face challenges such as reaching decision-makers who may be unavailable or less willing to discuss policies outside regular business hours. However, weekends can also provide opportunities to connect with clients who are too busy during the week. Successful agents typically adapt by being flexible with their scheduling, offering virtual consultations, and focusing on relationship-building. Proactive communication and clear follow-ups are key strategies to overcome these challenges and maximize weekend productivity.

Can I sell insurance on weekends?

Insurance sales jobs often offer flexible schedules, and many agents sell policies on weekends to accommodate clients' availability. However, specific working hours depend on the employer, licensing requirements, and whether the role involves in-person or remote sales. It is common for insurance agents to work outside traditional weekday hours, including weekends, especially during busy periods or for client convenience.

Can I do insurance sales as a side hustle?

Insurance sales can often be pursued as a side hustle, as many agents work part-time or freelance to supplement their income. Success typically requires obtaining relevant licenses, such as a state insurance license, and dedicating flexible hours to client meetings and sales activities.

What is the difference between Insurance Sales Weekend vs Insurance Agent?

AspectInsurance Sales WeekendInsurance Agent
CertificationsOften no formal certifications required, but some knowledge of insurance products helpsRequires state licensing and certifications to sell insurance
Work EnvironmentTemporary, event-based, often part-time or seasonalFull-time or part-time, office or client-facing settings
Employer & Industry UsageUsed by insurance companies for promotional or sales eventsEmployed directly by insurance companies or agencies to sell policies
Search & Comparison IntentPeople looking for short-term sales opportunities or event-based rolesIndividuals seeking ongoing sales careers in insurance

Insurance Sales Weekend roles are typically short-term, event-based sales opportunities that may not require formal licensing, whereas Insurance Agents are licensed professionals who sell insurance policies on a regular basis. The roles differ mainly in duration, certification requirements, and employment structure, with Insurance Agents pursuing continuous careers in the industry.

What are the key skills and qualifications needed to thrive as an insurance sales professional working weekends?

To thrive as an Insurance Sales professional on weekends, you need strong sales abilities, knowledge of insurance products, and typically a state-specific insurance license. Familiarity with CRM software, online quoting tools, and digital communication platforms is often required. Excellent interpersonal skills, self-motivation, and the ability to build trust quickly help you stand out in this customer-facing role. These skills ensure you can effectively engage clients, close sales, and maintain compliance in a competitive, time-sensitive environment.

Why do most insurance sales weekend agents quit?

Most insurance sales weekend agents quit due to the challenging nature of the job, which often involves high rejection rates, inconsistent income, and the need for strong sales skills. The part-time schedule and pressure to meet sales targets can also lead to burnout and job dissatisfaction.

What is an insurance sales weekend job?

Insurance Sales Weekend jobs involve selling insurance policies—such as auto, health, life, or home insurance—primarily during weekends. These roles may suit individuals seeking part-time or flexible work schedules, such as students or those supplementing existing income. Weekend insurance sales agents engage with potential clients, assess their insurance needs, explain policy options, and help customers choose the best coverage. The role often includes a mix of phone, online, and in-person interactions, and may involve meeting sales targets or earning commission.
What are the most commonly searched types of Insurance Sales jobs in Portland, OR? The most popular types of Insurance Sales jobs in Portland, OR are:

Insurance Sales Representative

Summit Business Group

Beaverton, OR • On-site

Full-time

Posted 28 days ago


Job description

Position: Direct Insurance Sales Representative

Number of Openings: 1 Territory Sales Position Available

About Us:

At Summit Business Group, we're not just another insurance agency. We're a powerhouse, committed to delivering top-notch supplemental benefits plans to small and medium-sized businesses. We thrive on strength, resilience, and the drive to succeed. If you're a natural leader who thrives on challenges and wants to be part of a winning team, we want you as our Direct InsuranceSales Representative.

The Role: As a Direct Insurance Sales Representative, you will be in control, managing your schedule and driving your success. You'll connect with business owners and key decision-makers, showcasing your ability to understand their needs and offer superior insurance solutions that stand out.

In the field, you'll take charge, using our advanced Salesforce CRM to engage potential clients through cold calls and in-person visits. Your mission: close deals and become the go-to advisor your clients can rely on. Your assertiveness and confidence will ensure clients feel valued and understood. You'll maintain these relationships with strong, effective communication, handling inquiries decisively, and providing unwavering support, particularly during the claims process.

What We're Looking For:

  • Proven experience in sales or customer-facing roles, especially in outside sales.
  • Ability to conduct comprehensive training cycles, both in-person and online.
  • Superior organizational, communication, and presentation skills.
  • A passion for empowering clients and a strong sense of responsibility for their well-being.
  • Health & Life general lines license, or the drive to obtain it within 90 days (with our support).

Position Overview:

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: Selling Business to Business

  • 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, 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 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 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.

Ready to elevate your career at a company that appreciates your nurturing nature? Apply now and let's make a difference together.

Learn more and apply at:www.yoursummitinsurance.com