Sales Representative

Steadily is an insurance technology company that specializes in rental property insurance for landlords. We’re five years old, just over 160 people, manage $20B in risk, and are intent on becoming the world’s best and largest insurer of rental properties.

We exist to deliver fast, affordable insurance and to pay claims quickly and fairly. To do that, we hire the best engineers, actuaries, sales, and service people in the country to build the experience that we’d want if we were the client.

We’re excited to be hiring top notch sales reps in our Overland Park, KS office! This is an on-site role with no P&C insurance experience required. We’ll pay for your licensing and training so you can hit the ground running. You'll be surrounded by other sales agents who are the best at what they do which will just make you even better.

What You'll Do

• Advise prospective investors who need help selecting coverage for their rental properties.

• Collaborate with your small team of advisors to provide a stellar customer experience by focusing on daily relationship management duties such as:

  Analyze in-force policies and current customers to identify opportunities to round out portfolios or establish partnerships.

  Negotiate with insurance company underwriters to secure timely and accurate quotes.

  Prepare rewrite presentations to bind and reissue policies.  

• Convert incoming opportunities to sales through text, phone, or email by rapidly responding to customers who have requested assistance securing an insurance policy on our site.

• Generate new business leads based on lost accounts, industry listings, networking, and referrals

• Adapt to new and ever changing technology as we build our processes and workflows.

• Collaborate with marketing and advertising teams to develop and implement effective sales campaigns.

• Provide subject matter expertise to our product and engineering teams so we can quickly improve our product for our customers.

• Manage a portfolio of lost accounts-identifying reasons for the loss and developing strategies to win back business.

• Stay up to date with industry trends and changes in insurance policies and regulations.

Your Background

• Experienced: You have a minimum of two years of experience in a high intensity sales environment. Experience in insurance or financial services is a plus.

• Digital: You have above-average computer skills and can adapt to new technology quickly.

• Hungry: You are driven by love of the sale. You’re competitive and know how to hustle to get things done quickly for your customer.

• Self-Driven: You are disciplined and are comfortable executing every day without being told what to do. You know what needs to be done and you do it without being asked. You are comfortable being held accountable to your results.

• Ambitious: You don't watch the clock when you are working towards your goals. Achieving your goals could take you beyond the traditional 8-5 and you’re willing to do what it takes to hit your targets.

Licensing

• You must successfully complete your state’s Property & Casualty licensing exam

• Steadily will reimburse you for the study materials and 1 exam attempt upon successful completion

• We will handle securing your non-resident licenses.

Compensation and Benefits

• $80,000 - $175,000 total compensation with no cap on commission earnings. Includes a higher than industry standard base salary of 60k.

• Equity in the company

• 3 weeks PTO plus six federal holidays

• Health insurance including Medical, Dental, Vision, Life, Disability, HSA, FSA 

• 401K

• Free snacks & regular team lunches

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 Us

• You'll be in good company. Our founders have three successful startups under their belt and have recruited a stellar team to match.

• We pay top of market (see comp).

• We're earlier stage, so you'll get to wear a lot of hats and shape product decisions.

• We have a good time. Culture matters a ton to us.

• We're growing fast and are exceptionally well-funded.

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

• Steadily was awarded Top 2025 Startups in Newsweek, 2025 Best Landlord Insurance Company by Investopedia, #6 on INC Regional’s Fastest-Growing Companies, a Winner of Austin Business Journal’s 2025 Best Places to Work, and #44 on the 2025 Forbes List of Best Startup Employers.

We’re excited to meet you!

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