Chief of Staff (Startup)

Chief of Staff (Startup)

The company is onsite in Union Square but there are no set days in office. The team is very flexible with no micro-management (major emphasis).

Compensation: $115K-$135K + equity + full healthcare benefits covered + annual health and wellness credit

Company Summary: We are a fast-growing, globally distributed consumer technology startup operating at the intersection of rideshare, mobility, and autonomous vehicle data intelligence. Our platform empowers consumers to compare rideshare prices in real time across providers, and our proprietary data and market insights are regularly cited by leading industry publications. We are a small, high-trust team with an entrepreneurial culture that values speed, creativity, and genuine impact.

Position Summary

We are seeking a highly motivated and organizationally exceptional Chief of Staff to serve as the right hand to our newly appointed CEO. This is a rare opportunity to operate at the center of a high-growth startup — managing executive operations, driving sales and growth support, and leading strategic research initiatives across the business. The ideal candidate is ambitious, detail-oriented, AI-native, and eager to grow into a leadership role within 18 to 24 months.

What You Will Do

Executive Administration, Finance and Operations — 40%

• Manage and optimize the CEO's calendar, ensuring priorities are protected and deadlines are met
• Own client billing and invoicing processes, ensuring accuracy and timeliness
• Manage vendor and contractor payments and build financial operations systems from the ground up
• Coordinate with an external CFO and accounting teams on key financial metrics and reporting
• Prepare board meeting materials, annual budget documentation, and financial summary slides
• Plan and coordinate company retreats, conference travel, site visits, and executive meetings

Sales and Growth Support — 30%

• Serve as an active partner to the CEO in the client acquisition and deal-closing process
• Build and manage the company CRM, ensuring pipeline data is clean, current, and actionable
• Develop and refine sales pitch materials and supporting documentation
• Execute timely follow-up with prospects and clients on behalf of the CEO
• Participate in sales and partnership brainstorms and contribute strategic ideas

Strategic Priorities and Special Projects — 30%

• Conduct research into market trends, competitive landscape, and emerging developments in rideshare, mobility, and autonomous vehicles
• Attend and take detailed notes in investor, partner, and cross-functional meetings — synthesizing insights into clear next steps
• Support the development and execution of go-to-market strategies for new product lines
• Provide flexible, high-quality support across any project or initiative that advances company growth

Your First 90 Days

In your first 90 days, you will focus on deep immersion — sitting across departments, building relationships with the team, and understanding the biggest operational challenges facing the business. You will shadow the CEO closely, learning her working style and gradually taking over operational tasks so she can remain focused on growth and strategy. You will also conduct structured research into new product lines and contribute to early GTM thinking. Listening, asking smart questions, and taking fast action are the three things that will define your success in this window.

Qualifications

• Two to eight years of experience in executive administration, management consulting, startup operations, sales support, or a combination thereof
• Demonstrated experience in a fast-paced, ambiguous, and entrepreneurial environment — startup experience strongly preferred
• Strong written and verbal communication skills with the ability to represent the CEO professionally across internal and external contexts
• Excellent organizational and systems-thinking capabilities — you track moving parts, close loops, and connect dots across the organization
• Comfort with financial operations tasks including invoicing, vendor management, and basic budget coordination
• Hands-on experience with CRM tools and sales support workflows
• Proficiency with tools including Notion, Airtable, Google Workspace, and Slack
• AI-native mindset — you actively incorporate AI tools into your daily workflow to improve speed and output quality
• High emotional intelligence, discretion, and the ability to build trust quickly with a new executive leader

Who Thrives Here

You are someone who sees no task as beneath you and no challenge as too large. You move fast, communicate clearly, and follow through without being reminded. You are as comfortable building a financial tracking system as you are taking notes in an investor meeting or hauling swag to a conference. You want real experience, real ownership, and a launchpad for what comes next — whether that is business school, a leadership role in growth or product, or your own venture.