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Chief of Staff

FleetWorks' flagship platform helps match freight brokers with  book freight faster, more profitably, and with fewer human hours. We're backed by top-tier investors and trusted by industry-leading brokerages. This is a rare opportunity to join a fast-growing startup at the intersection of artificial intelligence and logistics.

Role Overview

We’re looking for a highly motivated Chief of Staff to work directly with the founders to accelerate execution across the company. This is a high-trust, high-impact role ideal for someone who thrives in ambiguity, enjoys building systems from scratch, and wants a front-row seat to company-building.

The ideal candidate sees this role as a stepping stone to starting their own company.

Key Responsibilities

  • Strategic Projects: Own high-priority, cross-functional projects from idea to execution. Examples may include go-to-market experiments, customer research, pricing strategy, or internal automation.

  • CEO Enablement: Act as a thought partner to the executive team — preparing materials, managing priorities, and ensuring follow-through on key decisions.

  • Board & Investor Support: Coordinate board meetings, investor updates, and data room prep.

  • Culture Stewardship: Help shape and protect the company culture as we scale.

Who You Are

  • 3+ years of experience in high-growth startups, consulting, investing, or operations.

  • Has worked in or around logistics or is very excited to learn about the industry.

  • Comfortable communicating with enterprise executives or SMB business owners.

  • Exceptionally organized and detail-oriented, but not bogged down by perfectionism.

Why This Role

  • Work directly with the CEO and executive team

  • Gain exposure to every function of a fast-growing startup

  • Help scale a leading AI agent company solving real problems

  • Fast path to leadership opportunities as the company grows

Compensation:

  • Competitive salary + equity (We’ll tailor comp to the right candidate.)

  • Benefits include:

    • Health plan

    • Unlimited PTO

    • Fully covered lunches and dinners

Average salary estimate

$110000 / YEARLY (est.)
min
max
$90000K
$130000K

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, FleetWorks

Join FleetWorks as our Chief of Staff and embark on a thrilling journey at the forefront of innovation in logistics and artificial intelligence. Based in San Francisco, this role offers a unique opportunity to work closely with our founders and play a pivotal part in accelerating the execution of strategic initiatives across the company. As Chief of Staff, you will take ownership of high-priority projects that span various functions, from go-to-market experiments to internal automation. You'll be a thought partner to our CEO and executive team, preparing important materials and managing priorities to ensure that key decisions are executed flawlessly. Your involvement will extend to coordinating board meetings and investor updates, all while supporting the growth and nurturing of our company culture. We're looking for someone with at least 3 years of experience in startups or consulting who is not just organized and detail-oriented, but also passionate about learning logistics. If you thrive in an environment of ambiguity and possess a drive to innovate, FleetWorks is the place for you. This is more than just a position; it’s a stepping stone to empower you toward future leadership roles in the industry. With competitive salary options, equity, and all the perks like unlimited PTO and covered meals, you'll be perfectly positioned for personal and professional growth while making an impact in a rapidly evolving market.

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

As the Chief of Staff at FleetWorks, you'll be handling high-priority, cross-functional projects from inception to execution. This includes working on strategic initiatives like customer research, pricing strategy, and go-to-market experiments. Additionally, you'll enable the CEO by managing priorities and preparing essential materials, as well as coordinating board meetings and investor updates.

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What qualifications are needed for the Chief of Staff role at FleetWorks?

To qualify for the Chief of Staff position at FleetWorks, candidates should have at least 3 years of experience in high-growth startups, consulting, or operations. It's beneficial to have familiarity with the logistics industry, but a strong eagerness to learn is equally valued. Exceptional organizational skills and the ability to communicate effectively with executives are also crucial.

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What makes FleetWorks a great company for the Chief of Staff to work for?

FleetWorks stands out as a great workplace for the Chief of Staff because it offers a unique opportunity to work directly with the CEO and executive team, providing unparalleled exposure to all functions of a fast-growing startup. The company is also backed by top-tier investors, ensuring a strong foundation for growth and innovation in the logistics space.

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What is the company culture like at FleetWorks for a Chief of Staff?

At FleetWorks, we cultivate a dynamic and inclusive culture that values collaboration and innovation. As Chief of Staff, you'll help shape and protect this culture as we scale, ensuring that our values align with our goals. We encourage all team members to contribute ideas and engage in decision-making processes.

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What career growth opportunities can a Chief of Staff expect at FleetWorks?

The Chief of Staff role at FleetWorks is designed as a fast-path to future leadership opportunities. By working closely with the executive team and being involved in critical business decisions, you'll gain invaluable experience and insights that can propel your career forward in the logistics and AI sectors.

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Common Interview Questions for Chief of Staff
What inspired you to apply for the Chief of Staff position at FleetWorks?

To answer this, reflect on FleetWorks' vision and goals. Express your passion for logistics and AI, and how this aligns with your career aspirations. Mention your desire to contribute to a impactful startup environment.

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

Share strategies that work for you, like maintaining flexibility, prioritizing tasks, and relying on data-driven decision-making. Giving an example will show that you can effectively navigate uncertain situations.

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Describe a high-priority project you successfully managed.

Detail a specific project, emphasizing your role, the challenges faced, and the ultimate outcome. Make sure to highlight your organizational skills and how they contributed to the project's success.

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How would you prioritize tasks when supporting the CEO?

Discuss methods you use, like creating a priority matrix or utilizing project management tools. Demonstrating your approach will illustrate your capability to manage competing demands efficiently.

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What experience do you have in board and investor relations?

Describe any past experiences coordinating meetings or managing communications with executives or investors. Highlight your attention to detail and ability to present information clearly.

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How do you envision shaping the culture at FleetWorks?

Share your understanding of FleetWorks’ values and how you would promote them. Discuss initiatives you might advocate for, such as team-building activities or feedback mechanisms to ensure continual culture enhancement.

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Can you provide an example of a time you worked closely with executives?

Choose a relevant experience and describe your involvement, the insights gained, and the value you added to the executive team. Focus on your collaboration and communication skills.

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What strategies do you use for effective communication with team members?

Discuss your preference for transparency and clarity in communication. Consider mentioning the importance of active listening and adapting your communication style based on the audience.

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How would you approach developing a new go-to-market strategy?

Outline a high-level process, mentioning market research, customer feedback, competitive analysis, and collaboration with various teams. Highlight your analytical and strategic thinking skills.

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What do you hope to accomplish in your first 90 days as Chief of Staff at FleetWorks?

Set specific goals, like understanding internal processes, building relationships with key stakeholders, and starting to implement early improvements based on your observations. This shows your proactive mindset.

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Full-time, on-site
DATE POSTED
April 4, 2025

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