Product Operations Specialist
Jerry · Toronto, ON
- Hybrid
- Full-time
- $100,000 / year
- Toronto, ON
Job highlights
- Drive product initiatives within the Growth team.
- Analyze user journeys and identify friction points.
- Own user feedback and bug resolution processes.
- Collaborate with Engineering, Design, and Marketing teams.
- Contribute to A/B testing and experiment design.
About the role
About Jerry.ai
Jerry.ai is building America’s first and only AI-powered super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million users, and have helped millions find better auto insurance — and we’re just getting started.
About The Opportunity
We're looking for a sharp, structured, product thinker to join our Growth team. This role is purpose-built for someone who has built strong problem-solving and analytical foundations — whether through consulting, strategy, or early product work — and is ready to apply those skills to real product ownership in a fast-moving, high-stakes environment.
You'll be embedded in one of the most important teams at Jerry, working on the funnels that directly drive how millions of users discover, evaluate, and purchase car insurance. You'll start by building deep context across our product and user experience, then take on increasing ownership — from scoped feature launches to larger growth initiatives — as you develop your product instincts and establish your impact.
This role reports to the VP of Growth and collaborates closely with Engineering (including our China-based team), Design, Analytics, and Marketing — with direct visibility to senior leadership including the CEO.
How You Will Make An Impact
You'll ramp up quickly by developing the sharpest possible understanding of our product:
- Conduct structured product walkthroughs to map user journeys, identify friction points, and build a ground-level view of how our funnels perform.
- Own user feedback monitoring — synthesizing signals from reviews, support, and research into actionable insights.
- Drive bug triage and resolution in partnership with Engineering, ensuring quality issues are prioritized and closed efficiently.
From There, You'll Take On Real Product Ownership
- Lead end-to-end delivery of product initiatives — starting with well-scoped launches like landing pages and compliance-driven features, and expanding from there based on your trajectory.
- Partner with Design and Engineering to ship thoughtful, high-quality user experiences that balance speed, clarity, and trust.
- Contribute to A/B testing, funnel analysis, and experiment design — developing the experimental mindset that defines great growth PMs.
- Help translate ambiguous customer problems into clear hypotheses, requirements, and roadmap priorities.
- Coordinate with our China-based engineering team, including maintaining daily overlap during China business hours to ensure tight execution.
Who You Are
- Exceptionally structured thinker: you break down complex problems clearly and communicate with precision.
- Strong customer empathy: you think in user emotions and mental models, not just metrics.
- Developing product and UX instincts: you can articulate why a flow works or doesn’t and want to get better at it.
- Data-driven: you’re comfortable forming and pressure-testing hypotheses using quantitative analysis.
- Hungry to build: you’re excited to move from frameworks and recommendations to actually owning and shipping product.
- You thrive in ambiguity and move fast without losing rigor.
Ideal Experience
- 2–3 years of experience in management consulting (MBB or equivalent), product management, or product/business operations.
- Willing to flex working hours to maintain 3–4 hours of daily overlap with China business hours for engineering coordination.
- Chinese (Mandarin) language skills are a plus, but not required.
Why You’ll Love It
- Join a profitable pre-IPO startup with capital, traction, and runway ($240M funded | 60X revenue growth in 5 years | $2T market size).
- Work closely with brilliant leaders and teammates from companies like Amazon, Better, LinkedIn, McKinsey, BCG, Bain.
- Disrupt a massive market and take us to a $10B business in the next few years.
- Our growth is driven by forward-thinking technology: Jerry.ai is getting mentioned in many conversations about our use of GenAI, such as this Forbes article.
- Be immersed in a talent-dense environment and greatly accelerate your career growth.
- Impact millions of users experience with car maintenance and auto insurance.
Equal Employment Opportunity
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 recruiting@jerry.ai.
Compensation & Benefits
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.
About Jerry.ai
Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets.
Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all.
We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started.
Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.
Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.
Key skills/competency
- Product Operations Specialist
- Product Management
- Growth Initiatives
- User Feedback Analysis
- Bug Triage
- A/B Testing
- Data Analysis
- UX Instincts
- Structured Thinking
- Problem Solving
Skills & topics
- Product Operations Specialist
- Product Management
- Growth
- Operations
- Specialist
- Analytics
- User Experience
- Funnels
- A/B Testing
- Strategy
How to get hired
- Tailor your resume: Highlight experience in product management, consulting, or operations, emphasizing problem-solving and analytical skills.
- Showcase structured thinking: Provide examples of how you break down complex problems and communicate solutions clearly.
- Demonstrate data-driven approach: Include specific instances where you used quantitative analysis to inform decisions or test hypotheses.
- Emphasize user empathy: Share experiences where you considered user emotions and mental models to improve product flows.
- Prepare for collaboration questions: Be ready to discuss how you work with cross-functional teams, including international engineering groups.
Technical preparation
Behavioral questions
Frequently asked questions
- What are the key responsibilities for a Product Operations Specialist at Jerry.ai?
- As a Product Operations Specialist at Jerry.ai, you will be responsible for understanding the product deeply, mapping user journeys, identifying friction points, managing user feedback, driving bug triage, leading product initiatives from conception to delivery, partnering with design and engineering on user experiences, and contributing to A/B testing and experiment design. You'll also coordinate with our China-based engineering team.
- What experience is ideal for this Product Operations Specialist role at Jerry.ai?
- The ideal candidate will have 2-3 years of experience in management consulting (MBB or equivalent), product management, or product/business operations. Strong problem-solving, analytical foundations, structured thinking, customer empathy, product and UX instincts, and a data-driven approach are essential. Willingness to adjust work hours for China team overlap is also important.
- Does Jerry.ai require Chinese language skills for the Product Operations Specialist position?
- Chinese (Mandarin) language skills are considered a plus for the Product Operations Specialist role at Jerry.ai, but they are not a strict requirement for this position. The role does require coordinating with the China-based engineering team, so some flexibility in working hours to ensure overlap is necessary.
- What is the work environment like at Jerry.ai for a Product Operations Specialist?
- Jerry.ai offers a dynamic environment within a profitable pre-IPO startup that is disrupting a massive market. You'll work closely with experienced leaders and teammates from top companies, be immersed in a talent-dense setting, and have the opportunity to accelerate your career growth by impacting millions of users with forward-thinking technology, including GenAI.
- How does Jerry.ai support career growth for a Product Operations Specialist?
- Jerry.ai provides a talent-dense environment where you can greatly accelerate your career growth. By working closely with brilliant leaders and teammates from top companies, you'll gain exposure to innovative technologies and have the opportunity to take on significant ownership, impacting millions of users and contributing to the company's ambitious growth targets.