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Chief of Staff to the CEO - job 1 of 9

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

$150000 / YEARLY (est.)
min
max
$120000K
$180000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Chief of Staff to the CEO, Jerry

Are you ready to take your career to new heights? Join Jerry as our Chief of Staff to the CEO in Palo Alto, where the future of car ownership is being rewritten! In this pre-IPO startup with a solid financial backing of $240 million and a staggering $2 trillion market size, you will work closely with Art Agrawal, our dynamic cofounder and CEO. Your role will be multifaceted, acting as an essential extension of Art by driving operational initiatives, facilitating crucial decisions, and enhancing his productivity. You'll be the bridge between the executive team and Art, ensuring seamless communication and alignment while fostering trust and credibility across departments. Your unique position will provide you with a comprehensive understanding of our company's daily operations and challenges. You will tackle special projects that aim to remove bottlenecks and streamline processes, ultimately helping Jerry to scale efficiently. With exposure to all functions of the company—from product development and operations to marketing and finance—you will gain invaluable insights that will accelerate your professional growth. If you are a structured problem-solver with a passion for strategy and execution, and if you thrive in a high-energy, involvement-driven environment, Jerry is the place for you. Together, we will strive toward our goal of becoming a $10 billion business in the next few years, all while revolutionizing the car ownership experience for our over 5 million customers. Join us, and let's build something amazing together!

Frequently Asked Questions (FAQs) for Chief of Staff to the CEO Role at Jerry
What responsibilities does the Chief of Staff to the CEO at Jerry have?

The Chief of Staff to the CEO at Jerry plays a crucial role in driving operational efficiency and alignment within the company. This involves overseeing high-priority projects, improving cross-functional processes, and acting as a liaison between the CEO, Art Agrawal, and various teams. The role requires strategic thinking to prioritize key initiatives, manage communications, and ensure accountability among team members to propel the company towards its ambitious goals.

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What qualifications are needed for the Chief of Staff to the CEO position at Jerry?

Candidates for the Chief of Staff to the CEO role at Jerry should have over 6 years of experience, ideally encompassing management consulting, venture capital, or private equity backgrounds. A Bachelor's degree in a STEM field, economics, or a related discipline is preferred. Familiarity with business operations, strategy, and a hands-on approach to solving complex challenges is essential. Additionally, candidates must be located in the San Francisco Bay Area or willing to relocate to the Palo Alto office.

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What skills are important for a Chief of Staff to the CEO at Jerry?

Important skills for the Chief of Staff to the CEO at Jerry include structured problem-solving, strong communication, and exceptional organizational abilities. The role requires a proactive approach to ownership and tenacity, especially in navigating high-stakes situations. Being able to synthesize data for decision-making, articulate insights to varied audiences, and maintain a well-managed schedule are crucial to thrive in this fast-paced environment.

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What kind of projects will the Chief of Staff at Jerry oversee?

The Chief of Staff at Jerry will oversee a variety of high-priority projects from inception to execution. This includes identifying process improvements across different departments to enhance operational effectiveness, developing performance metrics dashboards for the CEO, and partnering closely with teams to maintain alignment with long-term company goals. The role promises a dynamic array of responsibilities that drive impact across the organization.

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How does the Chief of Staff to the CEO at Jerry impact company growth?

The Chief of Staff to the CEO at Jerry significantly influences company growth by streamlining operations and facilitating effective communication throughout the organization. By identifying and eliminating bottlenecks that slow down progress, the Chief of Staff will help accelerate major initiatives that are vital for scaling the business efficiently, thus contributing directly to Jerry’s goal of becoming a $10 billion company in the coming years.

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Common Interview Questions for Chief of Staff to the CEO
Can you describe your experience with cross-departmental communication in past roles?

In addressing this question, you should provide specific examples of how you've facilitated communication and collaboration between different teams. Highlight any tools or strategies you've implemented to improve information flow and ensure alignment on project goals. Mentioning instances where this led to successful outcomes or efficiencies will strengthen your answer.

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How do you prioritize tasks when working on multiple projects simultaneously?

An effective answer would demonstrate your ability to organize and prioritize based on urgency and impact. Discuss your approach, be it through the use of project management tools, creating detailed to-do lists, or conducting regular check-ins with stakeholders. You might also mention a specific scenario where your prioritization skills resulted in successful project delivery.

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What strategies do you use to manage expectations among different stakeholders?

When answering, discuss your approach to stakeholder management, focusing on transparent communication, regular updates, and setting realistic timelines. You can enhance your answer by citing specific experiences where you effectively addressed misalignments or concerns and successfully managed relationships during high-stakes projects.

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How do you handle conflicts in a fast-paced environment?

A strong answer will reflect your ability to remain calm and diplomatic in conflict situations. Discuss a specific example where you navigated a disagreement, emphasizing your approach to mediation, active listening, and seeking mutually beneficial solutions that adhered to company goals.

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Can you share an example of a process improvement you've implemented?

Here, highlight a specific example where you identified an inefficiency in a process and the steps you took to rectify it. Explain the outcome and how it positively affected operations or team productivity. Showing tangible results will showcase your capability in creating impactful improvements.

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What metrics do you believe are important for evaluating company performance?

Discuss your knowledge of key performance indicators relevant to Jerry’s goals, such as customer acquisition costs, retention rates, and operational efficiency metrics. Mention how these can provide insights into overall company health and strategic pivots, underscoring your analytical mindset.

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Describe a time you had to make a quick decision with limited information.

Your response should focus on your ability to analyze the situation quickly and consider potential risks before making a decision. Use a specific scenario to illustrate your thought process, the decision made, and the resulting impact, demonstrating your quick-thinking and data-driven approach.

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How would you go about making Art Agrawal's meetings more efficient?

Your answer should detail techniques you would use to prioritize meeting agendas based on the importance of topics, identifying key stakeholders for each meeting, and suggesting follow-up actions to ensure accountability. This would show your understanding of effective time management and strategic meeting planning.

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What do you believe are the critical elements of a successful executive partnership?

A comprehensive response would address trust, open communication, mutual respect, and alignment on company goals. Cite past experiences where you successfully built relationships with executives or team leaders, emphasizing the importance of understanding their vision to support their effectiveness.

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How do you ensure team alignment with the overall company strategy?

Mention your approach to creating clear communication channels, regular check-ins, and reporting mechanisms that emphasize transparency. Highlight specific tools you have used to track progress toward strategic objectives, ensuring all team members remain informed and engaged with the company’s vision and goals.

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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.

423 jobs
MATCH
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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 20, 2025

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