AI Native 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 is an AI-native services company selling outcomes to the freight brokerage industry. We do not sell software and expect our customers to figure out how to make it work. They hand us their operations, and we execute it as a service, paid per load.

Robin, our AI agent, does the bulk of the work end to end while our Heroes, a sharp human-in-the-loop team, handle the edge cases. Brokers get the scale and economics of software with the accountability of a services firm, and see ROI within weeks.

We are backed by Dynamo Ventures, Flybridge Capital, Field Ventures, Front Porch Venture Partners, and Tip Top VC. Our founder previously co-founded and sold Uello, a Latin American logistics company.

We are post-seed and in growth mode. The product, the customers, and the revenue are real, and now we are building the small team that takes the company to the next level.

About Freight Hero

Freight Hero is an AI-native services company selling outcomes to the freight brokerage industry. We do not sell software and expect our customers to figure out how to make it work. They hand us their operations, and we execute it as a service, paid per load.

Robin, our AI agent, does the bulk of the work end to end while our Heroes, a sharp human-in-the-loop team, handle the edge cases. Brokers get the scale and economics of software with the accountability of a services firm, and see ROI within weeks.

We are backed by Dynamo Ventures, Flybridge Capital, Field Ventures, Front Porch Venture Partners, and Tip Top VC. Our founder previously co-founded and sold Uello, a Latin American logistics company.

We are post-seed and in growth mode. The product, the customers, and the revenue are real, and now we are building the small team that takes the company to the next level.

About the Role

As Chief of Staff, you will work side by side with the CEO to run the business and bring AI deeper into how every team at Freight Hero works.

This is a founding role and the most cross‑functional seat in the company. You will own three things:

• AI across the business. Building and evangelizing the internal agents that power Freight Hero's own work, and the infrastructure that lets the whole team build their own.
• The operating backbone. Company cadence, cross‑functional projects, business reporting, people operations, and day‑to‑day finance alongside our external accounting partner.
• Generalist firepower. Jumping in wherever the company needs you most: the important, cross‑functional projects that need a curious generalist to own them. Think analyzing sales call transcripts to support sales enablement, digging into operational KPIs to sharpen our unit economics, coordinating outside legal counsel on a labor question in another country, or helping product and engineering get a release over the line.

The role is built for someone early in their career who builds with AI every day, moves fast, and wants to learn how a company is built and run. You bring the AI fluency and the hunger; the CEO brings the operating experience.

There is no established playbook; you will help write it. As functions mature, parts of your scope will spin out into dedicated roles.

Your First 90 Days

• Days 1 to 30: learn the business. Shadow the CEO and each team, map how work actually gets done, and take over the operating cadence and reporting.
• Days 31 to 60: ship your first agents. Automate the highest‑leverage workflows you found, starting with your own reporting, people ops, and finance work, and stand up the basic infrastructure and evals.
• Days 61 to 90: scale it. Roll agents out across teams, publish templates so others can build their own, and take on your first cross‑functional project for the CEO.

What Success Looks Like

• Internal agents are part of how every team works. They run reliably, with evals in place, and people use them because they save real time.
• New agents ship at a steady cadence, prioritized by leverage.
• Everyone on the team builds with AI, using the templates and guidelines you created.
• The business runs on cadence, and cross‑functional projects move forward without the CEO in every detail.
• People ops and finance run cleanly, and the CEO has the financial visibility needed to make decisions.
• Freight Hero does more with fewer people because of you.

Key Responsibilities

AI Across the Business: Build, Run, Evangelize

This is separate from Robin AI, our product. It is the AI we use to run Freight Hero itself.

• Hunt for the highest‑leverage workflows across every function. Sit with people, watch how they work, and find the loops worth automating.
• Prototype and ship internal agents continuously. Ship rough versions fast and iterate.
• Build and maintain the infrastructure these agents run on, including integrations with our existing tools (Slack, Google Workspace, CRM, HRIS, finance), deployment, and observability.
• Own the eval framework: define how each agent is measured and use evals to drive improvement.
• Create templates and guidelines that let everyone build and maintain their own agents safely.
• Be the internal evangelist and the go‑to person for "can we automate this?" Roll out agents alongside the teams using them and train people.
• Stay on the frontier and bring the best new tools and techniques into the company.
• Start with your own scope. The reporting, people ops, and finance work you own should be among the first things you automate.

Run-the-Business: Operations, People, and Finance

You own this work first, then automate as much of it as you can. The goal is for it to run with minimal manual effort, freeing you for higher‑leverage projects.

• Own the operating cadence: leadership meetings, business reviews, and the rhythms that keep the team aligned.
• Coordinate cross‑functional initiatives on behalf of the CEO, and turn data from across the company into clear reporting for leadership.
• Spot operational gaps and close them with lightweight processes, playbooks, and tooling.
• Support the CEO on hiring and onboarding: keep the funnel organized, coordinate interviews and candidate communications, and make sure new hires land well in their first weeks.
• Maintain basic people ops infrastructure (HR tooling, employee documentation, and policies), automating the repetitive parts.
• Own day‑to‑day finance with our external accounting partner, automate the routine workflows, and keep the CEO informed on cash, burn, and key financial signals.

Generalist Projects, Including Product

• Be the CEO's extra pair of hands on whatever matters most this quarter, from board materials to a pricing analysis to a brand‑new initiative.
• Support product and engineering with documentation, testing against real customer workflows, and turning customer feedback into clear requirements.
• Pick up new problems quickly, get to a working answer, and hand off cleanly once a function has its own owner.

What We Are Looking For

• 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. Exceptional candidates with less experience and a serious body of AI work are welcome.
• 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.
• Experience in logistics, freight, or B2B software is a plus, not a requirement.

Why Freight Hero

• Work directly with an experienced, previously exited founder.
• Get in on the ground floor of a venture‑backed startup with strong PMF signal and real customer traction.
• Real ownership across nearly every part of the business in your first year.
• Build with the best AI tools available, on real problems for a real business.
• A clear path as the company scales, whether leading internal AI, owning a function you helped build, or stepping into a more senior strategic seat.
• Competitive salary and equity in a venture‑backed company with significant upside.