Principal Product Manager, Steadily
Agent Quote Flow
$180-220k
+ Equity
Landlord insurance for rental property owners
Be an early applicant
Landlord insurance for rental property owners
101-200 employees
Be an early applicant
$180-220k
+ Equity
101-200 employees
Company mission
To bring fast, affordable landlord insurance to rental property owners.
Role
Who you are
- Experienced: This isn’t your first rodeo. There’s no specific requirement on years, but we expect you to ramp up quickly. You know how to balance speed and quality, making thoughtful trade-offs to solve problems effectively
- Builder: You’ve been a builder before, not just a planner. You’ve taken ideas from inception to launch over and over. You’re heavily biased towards action
- System-thinker: You thrive on untangling complex problems. You can deconstruct an entire user flow into its parts, understand how each piece fits, and spot the dependencies others miss. Underwriting workflows are full of edge cases and that excites you
- Stakeholder-whisperer: You synthesize what agents, underwriters, and the business each want and need, then make the call on how to proceed. You earn trust through attention to detail and follow-through
- Design-oriented: We have a designer, but you’ve spent enough time in Figma with wireframes and mockups that you have a strong sense for good UX. You set a high bar for what actually ships
- Driven: You should be excited about startups and not looking for an easy job. This is a commitment, but it’s a commitment that will set you — and as a byproduct, the company — apart. You’ll be surrounded by a team with high ownership who are genuinely fun to work with
What the job involves
- We’re hiring a Principal Product Manager to own the core quote flow, and intersection of the underwriting and agent experience. This is a full-time, in-office position based in Austin, TX
- Your two primary customers are the agents who quote with us every day and the underwriters who review and approve those quotes. As a Principal Product Manager, you’ll translate the complex details of underwriting into a seamless, trustworthy experience for agents. You’ll balance protecting our book with creating a frictionless quoting experience -ensuring our risk discipline shows up as clarity and confidence, not constraint
- This team drives revenue growth while maintaining disciplined risk selection. This is a senior, high-ownership IC role. You’ll work closely with engineering, design, operations, actuarial, and the executive team to set direction, make decisions, and ship impact that compounds over time
- Own the agent quote experience. Reduce the friction and ambiguity agents encounter throughout the quoting lifecycle from the moment they start a quote through to the very end. Your goal is enabling a one-call close
- Build intelligent underwriting systems. Work with engineering and underwriting to scale underwriting capacity through automation and model-driven decisions. You’ll help underwriters focus on nuanced, high-value cases by ensuring the routine is handled accurately by our systems
- Drive portfolio performance through product. Your work directly influences our most important metrics: close rate, quotes reviewed per underwriter, post-close action rates, and ultimately loss ratio. You connect product decisions to business outcomes and can explain why it matters
- Prioritize relentlessly. There are far more interesting problems to solve than you’ll have time to tackle. You’ll use data, business context, and good judgment to decide what’s most important, balancing the tactical (what needs to ship today) with the strategic (what stepping stones do we need for the next year)
- Collaborate across the organization. Work closely with Design, Engineering, Underwriting, and our Insurance teams to translate real-world user problems into clean, effective solutions. Your work won’t sit in JIRA tickets or Google Docs, it will ship fast, be used by agents and underwriters, and directly influence key product and business outcomes
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 utilising a digital approach, the company ensures landlords have access to the most competitive market rate, 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 addresses the growing demand for a more modern experience for insurers. The company's commitment to innovation is further supported by 2025 funding, which has positioned it to expand its market reach and product.
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
(Co-Founder & 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
(Co-Founder & CEO)Previously founded Silver Financial and Interviewed. Also worked as a Consultant at McKinsey & Co and as a Senior GM at Indeed.
David Tulig
(Co-Founder & 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.
Salary benchmarks
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