Principal, Pricing Intelligence

QUICK SUMMARY

Own how AI reshapes pricing at the company. Build tools that turn rate filings into rating engines, sharpen decisions, and expand AI's reach across the business.

WHO WE ARE

The company makes life simpler, more affordable, and better for homeowners — especially in the places where climate risks, rising costs, and outdated systems make it hardest. We start with smarter homeowners insurance and expand to everything homeowners need to thrive.

Using data, technology, and thoughtful human support, we're building products that are clear, fair, and help homeowners feel confident — so homeowners aren't left behind when they need help most.

Founded in 2016, the company is a remote-first employer with the companyfolk across more than 35 states. We serve customers in 14 states (and counting). Our disciplined growth, strong customer satisfaction, and focus on long-term sustainability fosters outstanding growth, attracts marquee investors, and earns recognition and accolades, including:

• Built In Chicago's Best Places to Work, Midsize Companies (2021-2026)

• Forbes' America's Best Startup Employers (2026)

• Inc. 5000 Fastest-Growing Private Companies

• Forbes' Fintech 50 (2023-2026)

• Great Places to Work Certified (2024-2026)

Most importantly, we're building the company to be a place where people do meaningful work with real impact — for our customers, our communities, and each other. We're excited to tell you more about how you can contribute to our rapid growth, strong unit economics, profitability, and excellent customer ratings. To learn more about how we work and what we're building, visit the company.com [link for members] and see how we work [link for members]

THE OPPORTUNITY

We're loothe companyg for a Principal, Pricing Intelligence to lead how the company uses AI to price homes more accurately in the toughest markets in the country. This role exists because our pricing challenges — climate volatility, regulatory complexity, and the pace at which the market moves — demand more than incremental improvement. They demand a new way of worthe companyg, and building it deserves a dedicated owner.

Reporting to the Chief Insurance Officer and worthe companyg closely with the companys Chief Analytics Officer and CEO, you'll take a portfolio of AI-driven pricing initiatives from concept to production, then expand AI's footprint into adjacent parts of the business. You'll shape how our pricing and risk management team makes decisions, how quickly we can act on market and portfolio signals, and how defensible our pricing is to regulators, reinsurers, and homeowners. The scope is unusually broad for a technical leadership role, and the impact is direct: better pricing means the company can keep serving homeowners in places others have written off.

YOUR RESPONSIBILITIES

• Own the company's AI-enabled pricing strategy end to end — from identifying opportunities to building tools that turn rate filings, competitor filings, and internal rating logic into executable, auditable engines

• Build AI-assisted pricing infrastructure, including transcription of rate filings, deterministic validation, quote tracing, book re-rating, and source-level provenance so every pricing decision is explainable and defensible

• Embed AI into the pricing and risk management team's core workflows — rate reviews, segmentation, filings, and portfolio monitoring — replacing manual, time-intensive processes with faster, more accurate ones

• Translate portfolio, market, and climate-risk signals into concrete pricing actions on rate adequacy, risk appetite, eligibility, targeted growth, and remediation

• Scout, prototype, and scale AI applications beyond pricing, identifying where AI can multiply the company's impact across underwriting, product, and operations

• Drive executive decision-mathe companyg by delivering clear, defensible analyses and recommendations to the Chief Insurance Officer, Chief Analytics Officer, and CEO

• Lead cross-functional collaboration with actuarial, underwriting, product, and data engineering to move AI-driven pricing initiatives from concept to production

SUCCESS IN THIS ROLE

In your first 6–12 months at the company, success is less about checthe companyg boxes and more about the impact you create. You'll use your skills and judgment to take ownership of meaningful work, improve how we operate, and help move the company's mission forward. Along the way, you'll deliver outcomes that make a real difference for both the companyfolk and the homeowners we serve.

By the end of your first year, you should feel confident in your role, trusted as an owner, and proud of the progress you've helped make.

• the company's CEO and Chief Analytics Officer have handed off AI-in-pricing exploration to a trusted owner, freeing them to focus on broader strategy

• At least one AI-assisted pricing tool is in production and adopted by the pricing and risk management team, with measurable gains in filing speed, pricing accuracy, or analyst leverage

• A prioritized roadmap of AI applications across pricing and adjacent functions exists, with early wins delivered and stakeholders aligned on what comes next

• The pricing team is mathe companyg faster, better-informed decisions on rate strategy, risk appetite, and remediation because of the tools and frameworks this role has built

WHAT YOU'LL BRING

HARD SKILLS

• FCAS or equivalent depth in P&C actuarial pricing, with 10+ years across primary insurance; homeowners experience strongly preferred

• Fluency in Python and SQL, plus worthe companyg experience with cloud data platforms like Databricks or Snowflake

• Experience leading discovery with internal users: mapping workflows, finding the costly manual steps, and validating solutions before scaling them

• Experience designing AI systems for regulated environments, including human-in-the-loop review, evaluation and accuracy testing, audit trails, and model governance that satisfies regulators

SOFT SKILLS

• Ability to communicate technical trade-offs and recommendations clearly to a C-suite audience

• Comfort operating with ambiguity — scoping your own work, prioritizing across competing opportunities, and moving from concept to production without a playbook

• Levels up the people around you: sets standards for how the pricing team uses AI and coaches analysts to adopt new tools

BONUS IF YOU HAVE

• Contributed to open-source insurance tooling or built auditable rating engines

• Reinsurance experience or exposure to catastrophe modeling for wind, wildfire, or severe convective storm perils

• Experience building executive dashboards that integrate carrier experience, benchmarks, and third-party data

HOW WE HIRE

We believe a great hiring experience should be clear, respectful, and human. We will accept applications for this position until December 20, 2026. While our recruiting team uses AI tools for efficiency, resumes are still screened by the company's in-house recruiters, and candidate evaluations and hiring decisions are made by recruiters and hiring teams. Rest assured, real people make real decisions.

The hiring process and timeline for each role will vary, depending on the position. However, here are some things you can expect from us:

• Prompt updates and feedback following interviews

• Interviews with recruiters, hiring managers, and members of teams

• Skills assessment relevant to the position, if applicable

• Genuine, thoughtful human interaction at every step

HOW WE SUPPORT YOU

We offer a comprehensive, competitive benefits program, allowing you to choose the benefits that are best for you and your family, starting on the first day of the month following your start date.

Core Benefits

• Competitive salary and company equity through Restricted Stock Units (RSUs), granted as part of our standard compensation package and based on role and level

• This role is eligible to earn additional compensation annually through participation in our the company Leadership Incentive Plan

• 401(k) with company match up to 4% of eligible earnings

• Multiple medical plan options, plus dental and vision coverage

• Company-funded HSA contributions (based on medical plan selection)

• Company-paid life insurance and short-term disability

• Employee referral bonuses

Health & Wellbeing

• A variety of supplemental benefit options, including long-term disability, critical illness, accident, legal, and pet insurance

• Access to mental health support and confidential counseling resources

• Flexible PTO for exempt employees (most employees take 15–20 days per year), plus 8 company-observed holidays

• Paid parental leave, including up to 14 weeks at 100% pay for birthing parents and 8 weeks at 100% pay for non-birthing parents

Growth & Development

• Career mobility and internal growth opportunities across the organization

• Professional development budgets for certifications, conferences, and learning available, subject to management approval

HOW WE WORK

We don’t just hire for skills. We hire for alignment. The companyfolk bring diverse perspectives, but we’re united by a shared set of values that shape how we work and how we show up for each other and our customers.

Run through walls, together - Every one of us is responsible for creating the culture we want to work in. High performance. Low drama. Always respectful. We assume the best in each other and challenge ideas, not intentions. We show up, work hard, and play to each other's strengths — because that’s how great teams win.

Raise the bar. Drop the ego - Attitudes are contagious. Every one of us is responsible for creating the culture we want to work in. High performance. Low drama. Always respectful. Like professional sports teams, we win by worthe companyg in sync. We show up, work hard, and play to each other’s strengths.

Act like an owner - We are owners, fully accountable for achieving the company’s mission. That requires positive, proactive, big-picture thinthe companyg well beyond our job descriptions. Ask questions, Take ownership. Do the right thing, even when it‘s hard. Because when the company thrives, so do you. And so do our customers.

Operate lean. Deliver more - We build efficiency into everything we do. Each dollar we save gets reinvested to deliver more to our customers: better pricing, more products, and new innovations. We work smarter by relentlessly prioritizing and using technology, including AI, to multiply our impact. Lean is about focus, not deprivation. Lean isn't a limitation — it's our competitive advantage.

Keep asthe companyg ‘What if?’ - We value curiosity. To make insurance better for our customers, we experiment. We embrace insights. And we base decisions on data rather than assumptions. We see setbacks as opportunities for growth and are always learning and improving. Both individually and as a company.

WHERE WE WORK

We are a remote-first company with offices in Chicago, IL and St. Petersburg, FL where teams can come together for collaboration.

For Sales Agents and Customer Service Agents: These roles sit in any of the following 32 states: AL, AZ, CO, FL, ID, IL, IN, KS, KY, LA, MA, MD, ME, MI, MO, MT, NC, NE, NM, NV, NY, OH, OK, PA, SC, TN, TX, UT, VT, VA, WA, and WI.

For all other positions, these roles can sit in any of the following 41 states: AL, AR, AZ, CA (exempt only), CO, CT, FL, GA, ID, IL, IN, IA, KS, KY, LA, MA, ME, MD, MI, MN, MO, MT, NC, NE, NJ, NM, NV, NY, OH, OK, OR, PA, SC, SD, TN, TX, UT, VT, VA, WA, and WI. Please only apply if you are able to live and work full-time in one of the states listed above.

For remote technical positions located in Canada, we are only able to hire individuals who reside in Ontario. Applicants must be able to live and work full-time in Ontario to be considered.

State locations and specifics are subject to change as our hiring requirements shift.

EEOC STATEMENT

The company is proud to be an Equal Employment Opportunity and Affirmative Action Employer. We don't just accept difference – we honor it, nurture it, and celebrate it. We don’t discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. The company welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates tathe companyg part in all aspects of the selection process. If you require accommodation, please contact us by sending an email to [link for members]