Assistant Underwriter

Location: Overland Park, KS (Kansas City Metro)
Employment Type: Full-time, In-Office
Department: Underwriting
Salary: $65,000/year + equity

Steadily is hiring an Assistant Underwriter to join our growing team in the Kansas City metro area. This is an exciting opportunity for someone who wants to start or grow their career in underwriting with one of the fastest-growing insurtech companies in the country. You’ll work closely with experienced underwriters, support daily underwriting operations, and learn the skills needed to thrive in the insurance industry.

This is a full-time, in-office position located in Overland Park, KS, where you’ll be at the center of our insurance underwriting and claims operations. This is an entry level role and direct underwriting experience is not necessarily required.

As an Assistant Underwriter, you will:

• Learn and apply the underwriting appetite and guidelines of our programs — we aim to say yes whenever possible while mitigating risk

• Work closely with underwriters on endorsements, tasks, renewals, applications, and quotes

• Provide timely support to internal and external agents, often addressing time-sensitive requests that help define our brand

• Process work across internal systems including Salesforce; quickly become a subject matter expert on our platforms

• Troubleshoot complex customer service and underwriting issues such as billing, inspections, nuanced risk profiles, and more

• Maintain high standards of accuracy in documenting underwriting files in our policy administration system

What We’re Looking For

• Strong verbal and written communication skills; able to remain professional and diplomatic under pressure. While direct underwriting experience is not required, transferable skills in detail-oriented, problem-solving, or customer-facing roles are valuable

• Tech-savviness and ability to learn new software systems quickly and independently

• Thrives under pressure, manages a heavy workload with minimal oversight, and never says “that’s not my job”

• A hunger and excitement to grow rapidly in an earlier-stage insurtech; motivated to roll up your sleeves and hustle

Compensation & Benefits

• Salary: $65,000 per year

• Equity: Stock options in a fast-growing company

• Time Off: 3 weeks PTO + paid holidays

• Benefits: Medical, dental, vision, life, disability, HSA, FSA, 401k

• Perks: Free snacks, team lunches, collaborative culture

Location & Schedule

• Office located in Overland Park, KS (Kansas City Metro)

• In-office schedule required; standard Monday–Friday business hours
  Steadily is building a workplace environment of team members who are passionate about working together in person. Our Kansas City office is central to our 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!