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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 | 40X revenue growth in 4 years | $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.)
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$120000K
$180000K

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

Are you ready to take your career to the next level? At Jerry, a pre-IPO startup based in Palo Alto, we're seeking a talented Chief of Staff to work closely with our co-founder and CEO, Art Agrawal. You’ll be an essential part of our dynamic team, taking ownership of various projects that range from tackling operational challenges to ensuring that Art can focus on what truly matters. In this role, you will help enhance the CEO’s efficiency by managing critical meetings and communications while fostering trust with our executive team as Art’s right-hand advisor. This is your chance to gain an insider's perspective on what makes a startup tick, interact with every part of our business—from product to marketing—and collaboratively pave the way for our ambitious goal of becoming a $10B company. If you thrive in a talent-dense environment where you can fast-track your career, this is the place for you! We're looking for someone who can identify bottlenecks and enhance cross-functional operations while maintaining our high-performance culture. With over 5 million satisfied customers and a 4.7-star App Store rating, Jerry is all about innovation and disruption. If you're up for a challenge and eager to make an impact while working alongside our brilliant team, don’t hesitate; we want to hear from you!

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

As the Chief of Staff to the CEO at Jerry, you will own a diverse range of projects that influence the company’s direction. Your main responsibilities include solving operational challenges, driving alignment on key initiatives, increasing the CEO’s efficiency, and maintaining accountability among teams. You’ll have the opportunity to engage with all facets of the company and help shape strategic decisions.

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What qualifications do you need to apply for the Chief of Staff to the CEO position at Jerry?

To apply for the Chief of Staff to the CEO position at Jerry, you should have at least 6 years of experience in fields like management consulting, venture capital, or business operations. A Bachelor's degree in a STEM-related discipline, economics, or a similar field is preferred. Familiarity with data-driven decision-making, strong organizational skills, and the ability to communicate effectively across all levels of the organization are essential.

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What type of work environment can you expect as Chief of Staff to the CEO at Jerry?

At Jerry, the work environment is vibrant, dynamic, and designed for innovation. As the Chief of Staff, you will collaborate closely with leaders from various departments within a pre-IPO startup. You’ll be surrounded by talented teammates who share a passion for disrupting the automotive market, creating a culture that values creativity, growth, and positive outcomes.

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What impact will the Chief of Staff to the CEO have on Jerry's business?

The Chief of Staff to the CEO at Jerry has a crucial role in driving the company’s success. By enhancing operational efficiencies, leading high-priority projects, and ensuring clear communication, you will help streamline processes that directly contribute to scaling our business. Your insights and actions will shape the strategic direction and operational framework as we aim to disrupt a massive market.

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How is Jerry committed to diversity and inclusion in the workplace for the Chief of Staff role?

Jerry is committed to fostering a diverse and inclusive workplace for the Chief of Staff to the CEO role. We proudly uphold equal employment opportunity principles, prohibiting discrimination based on various characteristics, and ensuring that all applicants receive a fair chance. We also offer reasonable accommodations for individuals with disabilities throughout the application process.

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Common Interview Questions for Chief of Staff to the CEO
Can you describe your problem-solving approach as a Chief of Staff?

When answering this question, emphasize your structured problem-solving methods and provide examples from past experiences where you've used data to drive decisions. Mention your ability to balance analytical thinking with intuition when data is limited.

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How will you manage competing priorities for the CEO?

To tackle this, share your strategies for organization and prioritization. Talk about tools you’ve used to manage schedules and how you ensure that the most important tasks align with the CEO's objectives while demonstrating your ability to navigate high-stakes situations.

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Describe a time you successfully executed a high-priority project.

In your answer, provide a specific instance where you led a project. Outline the challenge, your approach to rallying the team, securing resources, and ultimately delivering results. Make sure to highlight the metrics of success.

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What methods do you use to communicate complex information to different audiences?

Discuss your communication styles tailored to various audiences. Provide examples of how you've adapted your messaging for executives, teams, and external partners, ensuring clarity and engagement regardless of the audience.

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How do you build trust and credibility with executives in your role?

Explain how transparency, integrity, and reliability play into your interactions. Share examples of how you’ve built rapport through consistent communication, demonstrating accountability, and being proactive in flying under the radar to get things done.

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What is your experience with performance metrics and reporting?

Talk about your practical experience in monitoring and analyzing performance metrics. Highlight your ability to create dashboards or reports that inform decision-making, and how these have impacted a previous organization’s strategy.

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In your opinion, what makes a successful Chief of Staff?

Focus on essential traits like strategic thinking, strong communication, organizational skills, and emotional intelligence. Back your claims with examples of how these qualities have been vital in past roles you've held.

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Can you provide an example of conflict management in your previous roles?

Describe a specific conflict case and walk through your approach to resolving it. Show how you maintained professionalism and solved issues diplomatically while keeping the team's goals in mind.

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What excites you most about the opportunity to be Chief of Staff to the CEO at Jerry?

Express your enthusiasm for Jerry’s mission and the potential of the role. Connect your values and career aspirations with the opportunity to work in a talent-rich environment where you can make a significant impact.

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How do you ensure alignment across various teams within a company?

Discuss your strategies for fostering collaboration and communication among teams. Share past experiences where you facilitated discussions or implemented tools that aided in keeping all parties aligned with the company 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.

513 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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