Tech Lead Manager, Automation

You could be a TLM anywhere, why

• Join a pre-IPO startup with capital and traction ($2T market size, $240M funded, and we're profitable)

• Report directly to our cofounder/CTO and work closely with brilliant peers from companies like Nvidia, Meta, LinkedIn, Better, etc.

• Build the most critical and complex automation system in our product, and directly impact our ability to grow from 5M to 50M users and become a household name in the next few years

What is

Your car is one of the most expensive things you'll ever own, and the most unnecessarily complicated and painful to manage. is reimagining the entire user experience for everyday car owners in the U.S. – from insurance to driving insights to repairs – all-in-one mobile app.

Why you'll love working here:

• Real world impact: Your code touches millions of end users every day, and directly impacts our ability to convert customers and generate revenue.

• Meaningful work: Build systems and tools that automate hundreds of human agent hours and scale our business efficiently. You'll tackle different types of challenges every day, learning both the technical and business sides of our core products.

• Zero bureaucracy: Have an idea? Pitch it, implement it, and see it live in days. No red tape, no slow-moving processes.

• Brilliant & supportive teammates: Work with talented and kind people, who care intensely about their work. Be in an environment that encourages challenging the status quo, innovation, collaboration, and helping each other succeed.

About the opportunity:

Our insurance marketplace is our core product today, and our ability to fully automate the end-to-end shopping experience is our core differentiator. Insurance shopping is complex and requires many data inputs from different sources. The Sales Automation Team at owns the "last mile", the most critical part of that experience that fetches all the necessary data and completes sales automatically, directly impacting our revenue.

We're looking for a Tech Lead Manager who enjoys solving difficult puzzles and staying close to the code. Many of our Engineering Managers are ex-founders from high-stakes, high-concurrency industries like gaming and ad-tech. They joined us because they like solving difficult, impactful problems, and dislike bureaucracy, politics and other corporate fluff. Everyone here, including our cofounder & CTO, writes code and sweats the details.

What you'll own:

• This automation system was the first ever built at , because fo that, you will inherit a significant amount of tech debt. Because of the architectural refactoring needed, you'll be designing and implementing new systems, and pairing with engineers to establish the new standards. You will help drive a transition toward a cleaner, more predictable architecture.

• As the architecture improves, your focus will shift towards more design reviews, unblocking the team, and building the next generation of tools that allow us to scale.

• You will manage a team of 7 engineers across Toronto (5) and China (2).

Who you are:

• You're likely an ex-founder or have been the lead architect at a lean startup where you had to do a lot with a small team.

• You like to get your hands dirty and you're extremely detail-oriented. You won't stop until you understand exactly why a script failed, and you enjoy hunting for edge cases in complex business logic.

• You think like a business owner. You can balance trade-offs, and decide when to fix a bug and when to let it go to a human agent for the sake of higher impact work.

• You should have had some experience designing systems for offline, asynchronous jobs.

While we appreciate your interest and application, only applicants under consideration will be contacted.

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.

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

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

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, 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, 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. 

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.