Founding AI Chief of Staff

Freight Hero; New York (NY); On-site; USD 90,000 - 140,000; Full time

Benefits offered by this job

Competitive salary and equity

Job summary

Freight Hero in New York City seeks a Chief of Staff to work closely with the CEO, driving AI integration across the company and building the operating backbone. This founding role will own the AI strategy, the cadence of the business, and high‑impact, cross‑functional projects.

You will lead internal agents, finance, and people ops, while partnering with product and engineering to move initiatives forward. Base in NYC with travel to Durham, NC.

Qualifications

• 1 to 4 years in high-ownership roles such as startup operations, product or program management, forward‑deployed engineering, consulting, or founding something of your own.
• Deep AI fluency. You build with AI every day and can show us agents or tools that real people use.
• Comfortable with code. You can write Python, work with APIs, ship a deployment, and read other people's code without panic.
• A builder's mindset. You ship, close loops, and keep many workstreams moving without anything slipping.
• A true generalist. You can debug an agent in the morning and close out a financial reconciliation in the afternoon.
• Excellent communicator. You can write a polished CEO‑voice update and a clean SOP, and explain technical concepts to non‑technical people.
• High EQ. You build trust quickly and handle sensitive information with discretion.
• Hungry to learn and genuinely curious. You want to learn from an experienced founder, and you experiment with AI on your own time because you want to.
• Based in New York City and able to travel to Durham, NC regularly.

Responsibilities

• AI Across the Business: Build, Run, Evangelize.
• Run the Business: Operations, People, and Finance.
• Generalist projects including product and pricing analysis.
• Coordinate cross‑functional initiatives for the CEO.
• Support product and engineering with documentation and requirements.

Skills

AI fluency

Python

APIs

Generalist mindset

Strong communicator

Startup operations

Tools

Slack

Google Workspace

CRM

HRIS

Finance software

Job description

Freight Hero in New York City seeks a Chief of Staff to work closely with the CEO, driving AI integration across the company and building the operating backbone. This founding role will own the AI strategy, the cadence of the business, and high‑impact, cross‑functional projects.

You will lead internal agents, finance, and people ops, while partnering with product and engineering to move initiatives forward. Base in NYC with travel to Durham, NC.