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Chief of Staff - job 1 of 5

You could work anywhere. Why us?

  • Join a pre-IPO startup with capital, traction, and runway ($240M funded | $2T market size)

  • Work closely with brilliant leaders and teammates from companies like McKinsey, Bain, BCG, Better, Nerdwallet etc.

  • Disrupt a massive market and take us to a $10B business in the next few years

  • Be immersed in a talent-dense environment and greatly accelerate your career growth

About the opportunity:

We are looking for a Chief of Staff to work directly with our cofounder/CEO, Art Agrawal. You will act as an extension of our CEO and own a variety of projects ranging from solving operational issues, driving alignment and execution on critical initiatives, increasing Art's efficiency by helping him prioritize his most important meetings and communications, making decisions on his behalf, and keeping our teams accountable. You will foster trust and credibility with the rest of the executive team as the CEO’s closest proxy and advisor. Your main objective will be to identify and remove bottlenecks for our CEO and partner closely with him to scale our business. 

As the Chief of Staff, you'll own special projects and will have a unique opportunity to view and understand a company’s day-to-day challenges and priorities from the vantage point of a CEO. You will be exposed to every function at Jerry (product, operations, finance, engineering, data, marketing, etc) and learn how to execute big-picture strategies and navigate the intricacies of a complex business. If you’re looking for an opportunity to greatly accelerate your career trajectory, we’d love to hear from you!

How you will make an impact:

  • Identify and implement process improvements to streamline cross-functional operations, enabling Jerry to scale efficiently while maintaining a high-performance culture

  • Act as our CEO’s liaison, ensuring clear communication with internal teams and external partners, while effectively managing expectations and timelines

  • Build and maintain reports and dashboards to track company performance metrics, providing actionable insights to our CEO and leadership team to inform decision-making

  • Lead and oversee high-priority projects from concept to execution, working closely with different teams to ensure alignment with company goals

Preferred experience:

  • 6+ years of experience; ideally a mix of management consulting, venture capital, or private equity, and product, business operations, strategy or growth

  • Bachelor's degree in a STEM, economics, or related discipline

  • Must be located in the San Francisco Bay area or willing to relocate (you will be working on-site at our Palo Alto office)

What we are looking for:

  • Structured problem-solver: You’re a logical thinker and make decisions based on data, but also have good instincts when data is limited.

  • Owner: No challenge is too complex, no issue is too hard.

  • Tenacious: You’re comfortable navigating high-stakes, conflict-laden situations, and can act quickly and decisively with diplomacy and tact.

  • Extremely organized: You balance a packed schedule, an endless to-do list, and never let anything drop.

  • Strong communicator: You communicate effectively to a wide range of audiences (from senior executives to entry-level employees) and can masterfully tailor your approach to suit the circumstances.

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

Jerry 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 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@getjerry.com

About Jerry:

Jerry is America’s first and only AllCar™ app. We are redefining and radically improving how people manage owning a car, one of their most expensive and time-consuming assets. 

Backed by artificial intelligence and machine learning, Jerry 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 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 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.

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CEO of Jerry
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Art Agrawal
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Average salary estimate

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What You Should Know About Chief of Staff, Jerry

At Jerry, we're on a growth trajectory like no other, and we're looking for a dynamic Chief of Staff to join our team in Palo Alto, California. This isn’t just any role; it's a unique opportunity to work hand-in-hand with our cofounder and CEO, Art Agrawal. As Chief of Staff, you'll be the right arm of the CEO, stepping into the fast-paced world of a pre-IPO startup that's on the cutting edge of automotive technology. Your days will be filled with exciting challenges, solving operational puzzles, ensuring strategic initiatives align, and enhancing efficiency by optimizing the CEO's schedule and priorities. This role is perfect for someone with a knack for structured problem-solving and a passion for impactful communication. You’ll have the chance to collaborate across all functions – from product to engineering and marketing. You'll participate in high-priority projects, gaining unparalleled insight into our business's direction and day-to-day challenges. At Jerry, we cherish a culture of accountability, trust, and innovation, and as the Chief of Staff, you'll be instrumental in driving our mission forward. If you're ready to make your mark in a company poised to transcend the $10 billion mark within the next few years, we want to hear from you. This role promises not just a job, but a launching pad for your career where you can showcase your skills and contribute to an exciting mission. Together, let's revolutionize how people manage car ownership!

Frequently Asked Questions (FAQs) for Chief of Staff Role at Jerry
What responsibilities can I expect as the Chief of Staff at Jerry?

As the Chief of Staff at Jerry, your key responsibilities will include acting as a direct extension of the CEO, Art Agrawal, by overseeing critical initiatives, enhancing operational efficiency, and managing high-priority projects. You'll be responsible for streamlining communication between the CEO and various teams to ensure alignment with company goals.

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What qualifications are required for the Chief of Staff position at Jerry?

To qualify for the Chief of Staff role at Jerry, candidates should possess at least 6 years of relevant experience in fields like management consulting, venture capital, or operational strategy. A Bachelor’s degree in a STEM field, economics, or a related discipline is also preferred. Familiarity with technical and business operations will be a significant advantage.

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How does the Chief of Staff role at Jerry contribute to career development?

The Chief of Staff position at Jerry offers an exceptional opportunity for career growth. By working closely with the CEO and gaining insights into all facets of the business, you'll develop a unique view of operational challenges and strategic planning. This experiential learning is invaluable for anyone looking to advance in their career.

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Can you describe the work environment for the Chief of Staff at Jerry?

At Jerry, our work environment is dynamic and supportive, fostering innovation and collaboration. As Chief of Staff, you’ll be immersed in a talent-rich ecosystem where collaboration with high-performing teams is the norm, and where your contributions will directly influence the company's trajectory.

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Is there a possibility for remote work as Chief of Staff at Jerry?

The Chief of Staff role at Jerry is primarily on-site in our Palo Alto office, emphasizing the importance of in-person collaboration and communication. However, flexibility may be considered depending on specific project needs and circumstances.

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Common Interview Questions for Chief of Staff
What strategies would you employ to prioritize the CEO's schedule as Chief of Staff?

As Chief of Staff, I would implement an organized system that categorizes meetings based on urgency and strategic importance. Regularly reviewing the agenda with the CEO to adjust priorities would ensure that critical initiatives receive the attention they deserve.

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How do you plan to handle conflicts among team members at Jerry?

Handling conflicts requires a diplomatic approach. I would first listen to all parties involved to understand their concerns, then facilitate a meeting where we can collaboratively discuss solutions. Maintaining open lines of communication is key to preventing conflicts from escalating.

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Can you give an example of how you've driven operational efficiencies in the past?

In a previous role, I led a project to streamline communication across departments by implementing a shared dashboard. This resulted in reduced meeting times and increased transparency, ultimately enhancing decision-making processes and improving cross-departmental collaboration.

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What is your approach to managing high-priority project timelines?

I believe in effective project management through the creation of clear milestones and deadlines. By breaking projects into manageable tasks and regularly checking in with team members, I can ensure we meet timelines while adhering to high-quality standards.

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How do you ensure that information flows effectively between the CEO and other executives?

To ensure effective information flow, I would establish regular check-ins and updates that create a consistent loop of communication. Utilizing tools for collaboration will also help keep everyone on the same page, enabling agile responses to changing priorities.

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Describe a time when you had to make a difficult decision on behalf of your CEO.

In a previous role, I was tasked with deciding on a strategic partnership. After analyzing the data and weighing the pros and cons, I recommended proceeding to ensure we could leverage additional market reach while mitigating risks, ultimately resulting in a positive outcome for the company.

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How do you measure success in the Chief of Staff role?

Success in the Chief of Staff role can be measured by the efficiency of operations, the effectiveness of projects undertaken, and ultimately the CEO's ability to focus on strategic leadership responsibilities without being bogged down by operational details.

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What techniques do you recommend for building trust with team members?

Building trust requires active listening, transparency, and consistent follow-through on commitments. By showing that I'm approachable and reliable, I foster an environment where team members feel safe to express their ideas and concerns.

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How would you handle pressure and tight deadlines?

When faced with pressure, I prioritize tasks, creating a clear action plan to tackle deadlines methodically. I also remain adaptable, ready to re-evaluate and reallocate my focus as necessary, ensuring I meet commitments without sacrificing quality.

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What excites you about the Chief of Staff role at Jerry?

I am excited about the Chief of Staff role at Jerry because of the opportunity to work directly with a visionary CEO in a quickly evolving industry. The chance to drive meaningful impact while growing professionally in a collaborative and innovative environment is incredibly appealing to me.

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Jerry is redefining car ownership with its innovative AI-powered AllCar™ app, offering comprehensive solutions for insurance, financing, maintenance, and safety, driven by a team passionate about enhancing the driving experience.

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BADGES
Badge ChangemakerBadge Flexible CultureBadge Work&Life Balance
CULTURE VALUES
Social Impact Driven
Empathetic
Collaboration over Competition
Growth & Learning
Transparent & Candid
Customer-Centric
FUNDING
DEPARTMENTS
SENIORITY LEVEL REQUIREMENT
TEAM SIZE
EMPLOYMENT TYPE
Full-time, on-site
DATE POSTED
March 28, 2025

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