Principal Product Designer, Steadily
$175-215k
Offers equity
More information about location
4 days a week in office
Landlord insurance for rental property owners
Be an early applicant
Landlord insurance for rental property owners
101-200 employees
Be an early applicant
$175-215k
Offers equity
More information about location
4 days a week in office
101-200 employees
Company mission
To bring fast, affordable landlord insurance to rental property owners.
Role
Who you are
- The ideal candidate is practical, fast-moving, and user-obsessed
- You should be comfortable working in ambiguity, shipping iteratively, and collaborating closely with engineering and product to move quickly and make meaningful impact
- This isn't your first rodeo. There's no specific requirements on the minimum number of years, but we expect you to have strong visual and interaction design skills. You’re an expert in Figma from wireframes to high-fidelity prototypes
- You design for humans first. Whether someone is comfortable with tech or not, you care about creating intuitive, frustration-free experiences. You’re comfortable validating designs through user research and usability testing
- You love complex problems. Insurance is complicated. Each state has a different set of challenges and rules. You thrive on untangling it all and designing interfaces that make it feel simple and obvious
- You think in flows, not just screens. You’re always looking at the bigger picture: how users move through a journey, where they get stuck, and how to smooth their path with thoughtful interaction design
- You have taste and humility. You bring beautiful design to life, but you’re not going to die on every hill. You’re willing to compromise in favor of what actually works for users
- You’re a driver, not passenger. You don’t wait for perfect specs. You ask questions, propose solutions, and take initiative to push the work forward even when there’s ambiguity
What the job involves
- As our Principal Product Designer, you’ll own the experience layer of how landlords, insurance agents, and lenders interact with our platform from marketing collateral to our application
- You’ll work across the full design lifecycle: from hearing customer accounts firsthand to wireframes to polished UI, shipping intuitive, accessible, and efficient designs that serve a wide range of users, including those who are not always tech-savvy
- You’ll be responsible for extending and evolving our nascent design system
- Your work will ensure visual and functional consistency across the entire product ecosystem, while solving real-world problems with speed and empathy
- Own the end-to-end design process from discovery to delivery, iterating quickly and adjusting based on real usage data and team feedback
- Design user-friendly experiences across our marketing site, web application, and documents that helps landlords insure their rental properties
- Collaborate closely with Product, Engineering, and Operations to translate real-world user needs into clean, effective design solutions. Your work won’t sit in a Figma file, it will ship fast, be seen by users, and directly influence key product and business outcomes
- Create wireframes, prototypes, and high-fidelity mockups that balance user goals, technical constraints, and business objectives. You’ll run usability tests and gather feedback from diverse users including landlords and insurance agents to validate design choices and uncover blind spots
- Simplify complex data and workflows like coverage selection, policy document management, and production reports into clear, digestible visuals
- Review engineering PRs to ensure designs are built accurately and consistently. When things are off, you won’t just point it out - you’ll clearly communicate how to fix it
Application process
- Intro call - 15 mins
- Hiring manager interview with Christine - 45 mins
- Portfolio Review and Resume Deep Dive - 2 hours
- Paid Onsite Working Interview - 2 days
- We are looking for builders, not planners, so we strongly believe in hands-on interviews. You’ll spend 2 days in our office working alongside potential teammates and stakeholders
Our take
Steadily is a platform that caters to landlords, offering them a convenient and efficient way to explore and purchase insurance products for their residential properties. By utilizing a digital approach, the company ensures that landlords have access to the most competitive rate available on the market, simplifying the insurance acquisition process.
Having served over 18 million individual rental property owners, Steadily has earned a strong reputation for delivering fast, user-friendly, and affordable landlord insurance solutions. One of its standout features is the automation of certain data entry functions during the insurance quote application, making the experience burdensome for applicants and enabling them to receive quotes in a matter of minutes.
In an industry that has been slower to evolve, Steadily has addressed the growing demand for a more modern experience for insurers. The company's commitment to innovation is further supported by recent funding which has positioned it to expand its offerings and develop new products and services.
Freddie
Company Specialist at Welcome to the Jungle
Insights
60% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$30m
SERIES C
Jul 2023
$28.5m
SERIES B
Total funding: $90.1m
Company benefits
- Equity in the company
- Employer healthcare contribution
- 401K
- Flexible Time Off
- Health (HSA or FSA), vision, and dental insurance
- Equipment provided
- Continued education opportunities
Company HQ
Congress Avenue Historic District, Austin, TX
Leadership
Datha Santomieri
(COO)Previously worked as a Regional Insurance Operations Leader at Brown & Brown Insurance and as a Director of Project Management at Arrowhead General Insurance Agency.
Darren Nix
(CEO)Previously founded Silver Financial and Interviewed. Also worked as a Consultant at McKinsey & Co and as a Senior GM at Indeed.
David Tulig
(CTO)Graduated from the University of Texas with a BS in Computer Science. Previously worked at Indeed in multiple roles, including Senior Engineering Manager and Director of Engineering.
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