Licensed Health Insurance Broker / Benefits Sales Consultant

Workstream is a mission-driven company building the all-in-one HR, payroll, and hiring platform for managing the hourly workforce. There are 2.7 billion hourly workers, making up 80% of the global workforce, but this market has been heavily underserved by technology and deserves better. Workstream has been purpose-built for the hourly workforce from day one so that these businesses and their employees can thrive. Our customers include leading brands from multiple sectors, including Burger King, Carl's Jr./Hardee's, IHOP, KFC, and Culvers. We are a high growth series B company and quickly expanding our product portfolio to deliver on our vision. We are backed by legendary VCs and industry experts like Founders Fund, BOND, and Coatue. Grow With Us We are looking for a Licensed Health Insurance Broker / Benefits Sales Consultant to join Workstream. In this role, you’ll advise and sell health benefits and insurance plans to both existing and new Workstream customers across the U.S. You’ll partner closely with our sales, partnerships, and product teams to deliver compliant, affordable, and scalable benefits solutions that meet client needs. This is an ideal opportunity for a broker with 1–2 years of experience who’s looking for stability, career growth, and strong earning potential—without the burden of building a book of business from the ground up. This is a full-time, remote role. Candidates should be comfortable with occasional travel for in-person conferences (such as Culver’s or other brand conferences) and periodic company offsites, which may take place in Utah or San Francisco, to support collaboration and relationship-building. Day in the Life • Sell health insurance plans and benefits solutions to U.S. SMB employers • Advise customers on plan options, compliance, and best-fit coverage • Manage the full sales cycle: discovery → recommendation → close • Work warm leads and inbound opportunities generated through Workstream • Collaborate with internal sales, partnerships, and broker channel teams • Stay compliant with state and federal health insurance regulations • Maintain accurate records in CRM and benefits systems Who You Are • Active U.S. Health Insurance Broker License (individual producer) • 1+ year experience selling health insurance or employee benefits • Interest in working at a technology company (SaaS experience a plus) • Strong communication and consultative selling skills • Coachable, motivated, and excited to grow a long-term career • Comfortable working remotely with distributed teams Nice To Have • Experience with ACA, group health, or SMB benefits • Experience working at a SAAS company What We Offer • A mission-driven and value-based company dedicated to empower deskless workers and local businesses • An early employee opportunity at a Series B hyper-growth startup with over $120M in funding • Work directly with the founding team and industry veterans to accelerate your career • Uncapped Commission: Earn commissions on all health plans sold On-arenaflex Earnings: Strong six-figure potential for high performer • Comprehensive health coverage: medical, dental, and vision. We pay 95% of your premiums for our employees and 85% for dependents • In office amenities and stocked kitchen • 401K Plan • Pre-tax commuter benefits • Learning/development stipend • Flexible PTO Salary Range In accordance with the California Pay Transparency Law, this role offers on-arenaflex earnings of $140,000–$160,000 in Texas, based on a 50/50 base salary and commission structure. The role includes uncapped commission, with commissions earned on all health plans sold, providing strong six-figure earning potential for high performers. This range does not include discretionary bonuses or equity. Compensation is determined based on factors such as skills, experience, job scope, and current market data. Know More About Workstream • • • Additional Information Workstream provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training. We are committed to the full inclusion of all qualified individuals. Apply tot his job

Back to blog

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...