AI Native Chief of Staff

AI Native Chief of Staff

New York, New York

American farmers have made tremendous technology advancements through hardware improvements and investments in precision agriculture. However, when it comes to the back-office, most farms are decades behind, relying on spreadsheets, filing cabinets, and decades-old on-prem software to recruit, manage, and pay their workforce. Seso is addressing this problem by modernizing the back-office for the farm.

Our mission is to build the premier platform for agribusiness to hire and manage their workforce and improve the lives of agricultural workers. We are addressing American farmers' biggest pain point - access to qualified labor - through a software-enabled labor solution that automates the H-2A visa. Our comprehensive HR platform streamlines and automates the hiring process for farms and seamlessly integrates their efforts across recruitment, onboarding, payroll, and insurance while providing workers access to financial services for the first time.

Seso has raised over $60M from Tier I investors including Index, Founders Fund, and Mary Meeker at Bond, and has been recognized with awards including Forbes Rising Stars and Andreessen Horowitz's American Dynamism 50.

About the Role

We're hiring a Chief of Staff to work directly with our CEO on one of the highest-leverage initiatives in the company: rewiring how Seso operates so we can drive gross margin improvements and ship AI-native products to our customers. This is a deeply cross-functional role with a strong technical lean. You'll need to understand how every part of the business works: Sales, Marketing, Post-Sales, Operations, Finance, Product, Engineering, and you'll need to be comfortable getting under the hood to connect our internal systems to the latest AI tools.

You'll partner with the CEO on two interlocking mandates:

• Drive gross margin improvements across the company by identifying, designing, and implementing automation across every function.
• Identify AI-native product opportunities that Seso can bring to the farm.

This is not a traditional Chief of Staff role. You'll spend more time prototyping integrations, wiring up automations, and shipping than running calendars or board prep. If you've ever wanted to combine an operator role with deep technical work and CEO-level strategic exposure, this is that job.

What You'll Do

• Partner with the CEO to identify, prioritize, and execute against the highest-leverage automation and AI opportunities across the company.
• Map current workflows in each business function, surface inefficiencies, and design end-to-end solutions that combine internal tooling with AI.
• Build prototypes and ship lightweight integrations connecting Seso's internal systems (CRM, payroll platform, comms tools, data warehouse) to AI services and APIs.
• Quantify and track gross margin improvements driven by your work — close the loop between the change shipped and the metric moved.
• Identify, scope, and pressure-test AI product opportunities Seso can package and offer to our farm customers.
• Operate as a thought partner to the CEO on strategic priorities, special projects, and cross-functional initiatives that don't yet have a clear owner.
• Translate fluently between functions — make engineering legible to operators and operations legible to engineers.

What We're Looking For

• A product or engineering background you can lean on — you've built and shipped things and you understand how systems get wired together.
• Demonstrated fluency with modern AI tools — LLMs, agentic frameworks, automation platforms (Zapier, Make, n8n, Retool, and similar) — and the ability to prototype solutions that actually work in production.
• Strong business acumen. Comfortable reading a P&L, understanding gross margin levers, and translating operational metrics into priorities.
• High agency and a bias to ship. You see a problem, scope it, build the first version, and measure the impact.
• Excellent communication and stakeholder management. You can sit with a Sales leader in the morning, an engineer at lunch, and a finance manager in the afternoon and add value to all three conversations.
• Comfort with ambiguity. Much of the role is deciding what to do, not just doing what's assigned.
• Track record of impact in high-growth environments, ideally vertical SaaS, fintech, ops-tech, or an adjacent category.

Bonus Points

• Prior experience in a Chief of Staff, BizOps, or founding-operator role at a high-growth startup.
• Familiarity with the agriculture, labor, payroll, or HR-tech space.
• Engineering or CS background with production shipping experience.

Diversity is more than a commitment at Seso, it is the foundation of what we do. We pride ourselves on building the premier platform that serves agribusiness and improves the lives of agricultural workers. We believe in diversity of race, gender, sexual orientation, age, religion, ethnicity, national origin and all the other fascinating characteristics that make us all feel welcome.

Seso participates in E-Verify