Sales Representative – Insurance Training Provided

Location: Overland Park, KS (Kansas City Metro)Employment Type: Full-time, In-OfficeDepartment: SalesSalary: $60K base salary + uncapped commission, averaging $100K-$200K+ (top agents earn $200K+)

Launch your sales career with Steadily! We’re hiring motivated Sales Representatives to join our growing team in the Kansas City area. No insurance license required — we’ll pay for your training and licensing so you can hit the ground running.

Why Join Steadily?

• High Earnings Potential: Top agents earn $200,000+

  • $80,000 - $175,000 total compensation (competitive base + uncapped commission).. Includes a higher than industry standard base salary of 60k.

• Career Growth: Paid training, licensing, and opportunities to advance.

• Work with the Best: Join a top-performing sales team in a fast-growing insurtech company.

Your Background

• Experience: 2+ years in a customer facing role (insurance experience a plus, but not required).

• Tech-Savvy: Strong computer skills, ability to adapt to new tools quickly.

• Driven & Competitive: Motivated by sales goals and uncapped commission.

• Self-Starter: Takes initiative and thrives under accountability.

Compensation & Benefits

• High Earnings Potential: $60K base salary + uncapped commission, averaging $100K-$200K+ (top agents earn $200K+)

• Equity: Stock options in a fast-growing company

• Time Off: 3 weeks PTO + 6 federal holidays

• Insurance: Medical, dental, vision, life, disability, HSA, FSA

• Retirement: 401(k)

• Perks: Free snacks, team lunches, collaborative office culture

Location

• Overland Park, KS

• Steadily is building a workplace environment of team members who are passionate and excited to be together in person. Our office is in Overland Park, and is key to our fast-paced growth trajectory.

Why Join Steadily

• Good company. Our founders have three successful startups under their belt and have recruited a stellar team to match.

• Top compensation. We pay at the top of the Kansas City market (see comp).

• Growth opportunity: We’re an early-stage, fast-growing company where you’ll wear a lot of hats and shape product decisions.

• Strong backing. We’re growing fast, we manage over $20 billion in risk, and we’re exceptionally well-funded.

• Culture: Steadily boasts a very unique culture that our teammates love. We call it like we see it and we’re nothing if not candid. Plus, we love to have a good time. Check out our culture deck to learn what we’re all about.

• Awards: We've been recognized both locally and nationally as a top place to work. Recently we were ranked 16th on Forbes' 2026 Best Startup Employers list, and 63rd on the prestigious Inc 5000 Fastest Growing Companies list. We've also been recognized as one of the Best Landlord Insurance Companies in 2026 by CNBC, a Top 2025 Startup in Newsweek, in Investopedia's Best Landlord Insurance Companies, and we won Austin Business Journal's Best Places to Work in 2025.

We're excited to meet you!