Associate, Business Operations & Analytics

Jerry; Chicago (IL); Hybrid; USD 90,000 - 130,000; Full time

Benefits offered by this job

Health coverage

Dental coverage

Vision coverage

Paid time off

Paid parental leave

401(K) plan with employer matching

Wellness benefits

Equity opportunities may also be part

Job summary

Jerry is hiring for a Business Operations & Analytics role embedded within core business units like growth, product, AI, and partnerships. You will own the analytical function end-to-end, define the questions, build metrics and reports, and surface actionable insights to influence leadership decisions.

You will work across product, growth, finance, and operations to push initiatives from analysis to execution, with a strong emphasis on measurable impact and clear communication.

Qualifications

• Ability to break ambiguous problems into clear hypotheses before touching data
• Strong communication skills to explain complex findings concisely
• Ownership mindset and accountability for outcomes
• Experience pulling, structuring, and interpreting data independently

Responsibilities

• Define the right problems by clarifying business questions and decisions
• Build reports and run analyses to surface data insights that move key metrics
• Collaborate with product, growth, finance, and operations to drive decisions and outcomes

Skills

First principles thinking

Direct communicator

Owner mindset

Tools

SQL (Clickhouse)

Metabase

Python

Jupyter Hub

GitHub

Job description

Why We Exist

Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey — buy/sell, insurance, maintenance, repairs — is fragmented, complicated, and expensive.

Why We Exist

Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey — buy/sell, insurance, maintenance, repairs — is fragmented, complicated, and expensive. Jerry.ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We’ve reached 5M+ customers, raised $240M+, scaled revenue 70X, and became profitable in early 2024. We’re now expanding into adjacent verticals (e.g. home, motorcycle, RV, etc) to become the one-stop-shop for all your physical assets.

Why We’re Hiring

Our Business Operations & Analytics team has been a force multiplier and accelerant to our business that has helped us reach these pivotal milestones in spite of headwinds and within a highly competitive market. They are a team of former McKinsey, BCG and Bain consultants who drive data & insights, and inform decision‑making across every corner of our business. They are analytical powerhouses and first principles problem solvers who push forward our most important initiatives across product, growth, tech, and operations. Every business unit has a Business Operations & Analytics team member embedded within it — someone who doesn’t just run analyses and build dashboards, but shapes what questions we should ask, what data to pull, what conclusions to draw, what decisions to make, and then drives our teams towards our next goal: go from 5M to 50M customers and become a $10B business in the next 4 years.

• Growth Marketing
• Product Development
• AI & Automation
• Strategic Partnerships

On leveling:

You may see job ads for this role at different job levels. Our priority is finding the right people, we can be flexible with job title/leveling.

Why You Will (Or Won’t) Like Working Here

• No slides: If you’ve worked in consulting, you know what it feels like to be up at 3am reformatting a deck. That doesn’t exist here. The only work that gets done at Jerry is work that will materially change the trajectory of our business — an important product, a new growth channel, a key metric, a critical partner relationship, etc.
• No corporate fluff: The Business Operations & Analytics team is 14 insatiable learners who care deeply about solving difficult problems and making a tangible impact. Every person owns a critical domain. There is no bloat, unnecessary meetings, or waiting for approvals.
• Hands‑on: This is not a pure strategy role, you will also own execution. Your day‑to‑day will be surfacing analytical insights, driving decisions, and seeing them through end‑to‑end.

What You’ll Own

You’ll sit on our central Business Operations & Analytics team but you’ll be embedded in one of Jerry’s core business areas — growth, product, AI and automation, strategic partnerships — and own the analytical function for that business unit end‑to‑end.

• Define the right problems: Before any analysis, understand what business question it’s answering and what decision it will inform. Push back if the question is flawed.
• Data and insights: Define metrics, build reports, run analyses, design experiments, and surface data insights that move your team's key metrics.
• Drive outcomes: Bring recommendations to your counterparts in product, growth, finance or operations, tell them what’s happening and why, and what next steps should be.

Who You Are

• First principles thinker: You break ambiguous problems into clear hypotheses before touching data. You’re analytically strong (comfortable with SQL or Python) but your instinct is to ask “what are we trying to solve here?” before jumping to “what should I build?”
• Direct communicator: You can walk a skeptical stakeholder through a complex finding and get buy‑in quickly. You write clearly, speak precisely, and don’t bury the lede.
• Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.

What You’ll Bring

• 1+ years of experience at a consulting firm, investment bank, or high‑growth technology company.
• Strong analytical skills; ability to pull, structure, and interpret data independently.
• Track record of owning ambiguous problems and delivering impact.
• Clear, persuasive communicator who can influence decisions at the leadership level.

Our Tools

SQL (Clickhouse), Metabase, Python, Jupyter Hub, GitHub.

While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.

Jerry.ai is only able to hire full‑time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full‑time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at [e-mail]

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part‑time, contract, or freelance roles may not be eligible for certain benefits.

• Health coverage
• Dental coverage
• Vision coverage
• Paid time off
• Paid parental leave
• 401(K) plan with employer matching
• Wellness benefits
• Equity opportunities may also be part of your total rewards package

About Jerry.ai

Jerry is building the first AI‑powered advisor to manage all your physical assets. Your car, home, and motorcycle aren’t just purchases, they’re the physical embodiment of the life you’ve worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive. Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We’ve reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We’re now expanding into home, motorcycle, RV, and beyond. Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big‑hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft. We are proud to consistently rank as one of Y Combinator’s Top Companies, Forbes and Statista’s Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership. We are a remote‑first company, but if you prefer in‑person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.