Chief of Staff to the CEO - job 1 of 7

As the Chief of Staff to the CEO at Jerry, your key responsibilities will include managing critical initiatives that require your oversight, facilitating communication between the CEO and various teams, and ensuring project execution aligns with company goals. You’ll act as an extension of the CEO, helping prioritize tasks and meetings, and make decisions on behalf of the CEO when necessary. You'll work closely with other executives to foster strong collaboration, and you'll also lead special projects that help the company scale efficiently.

Jerry requires candidates for the Chief of Staff position to have at least 6 years of experience, ideally with a blend of management consulting, venture capital, or private equity in addition to product, strategy, or business operations experience. A Bachelor's degree in a related discipline such as STEM or economics is also required. Candidates must be located in the San Francisco Bay area or willing to relocate, as this role is on-site in Palo Alto.

The Chief of Staff supports the CEO at Jerry by acting as a liaison between the CEO and other teams. This role involves ensuring clear communication, managing expectations, and handling any operational roadblocks that may slow down progress. You'll also take on high-priority projects that require execution, allowing the CEO to focus on strategic decisions while you drive operational success.

Essential skills for the Chief of Staff role at Jerry include strong problem-solving abilities, excellent organizational skills, and outstanding communication prowess to effectively engage with diverse audiences. You should demonstrate a tenacious spirit, especially when navigating high-stakes situations, and possess the capability to prioritize a busy schedule and numerous tasks without letting anything slip through the cracks.

Jerry is an exciting place to work for a Chief of Staff due to its dynamic pre-IPO environment with significant funding and growth potential. You have the opportunity to impact a massive market valued at $2 trillion while collaborating with an innovative team of former industry leaders. Additionally, Jerry’s commitment to personal and professional development ensures that you can accelerate your career in a supportive and collaborative atmosphere.

When answering this question, focus on a specific project where you played a significant role. Outline the project's scope, the challenges you faced, and how you navigated them to completion. Highlight your problem-solving skills and mention the outcomes, making sure to tie it back to how such experience would benefit you as the Chief of Staff at Jerry.

Share your approach to prioritization by discussing frameworks or methods you use, such as the Eisenhower Matrix or Agile methodology. Provide an example of how you successfully prioritized tasks in a high-pressure situation and how your decisions impacted the team's efficiency or results.

Explain your strategies for promoting teamwork, such as regular check-ins, cross-functional workshops, or using collaborative tools. Use an example from your previous roles where your approach led to improved team dynamics and how this would apply as Chief of Staff at Jerry.

Describe your diplomatic approach to resolving conflicts, emphasizing communication and negotiation techniques. Mention a time when you successfully balanced competing demands and how that experience would inform your role at Jerry, particularly in supporting the CEO.

Talk about the tools and methodologies you utilize for tracking progress, such as Gantt charts, OKRs, or dashboard metrics. Provide specifics on how these methods keep stakeholders informed and engaged, reflecting on how this practice can help Jerry achieve its goals under your leadership.

Share examples of how you tailor your communication style to different stakeholders—from senior executives to entry-level staff. Emphasize your ability to connect with various audiences, ensuring clarity and understanding, which is essential for the Chief of Staff role at Jerry.

Reflect on a specific instance where you had to rely on instincts or experience to make a strategic decision despite incomplete information. Discuss the results and what you learned, connecting it to how you'll make decisions as Chief of Staff to the CEO at Jerry.

When answering this, be honest about the challenges while also framing them positively. Discuss how navigating competing priorities, managing stakeholder expectations, or driving cross-functional alignment can be challenging and share your strategies for overcoming these hurdles to thrive at Jerry.

Define success in the role by focusing on key outcomes like effective operational execution, positive team dynamics, and the ability to increase the CEO's efficiency. Provide metrics or qualitative examples that illustrate these success factors, showing how they align with Jerry's vision.

Express your passion for disruptive innovation and how being part of a pre-IPO startup like Jerry aligns with your career aspirations. Mention specific aspects that excite you, such as the opportunity to work closely with a visionary CEO or to impact a revolutionary product in the car ownership space.