Chief of Staff to the CTO

Description

The company sells an AI platform that helps government contractors respond to RFPs faster. Over the past year revenue grew 5x and daily active users grew 10x.

Customers include defense primes and top federal integrators, who run their RFP work on the product inside FedRAMP and AWS GovCloud environments.

Today the CTO owns the product thinking that links customer needs to what engineering builds. This hire takes over that work.

This is a generalist role beside the CTO. The company hires for trajectory more than years of experience, so you would learn how a company is built by working next to the person building it. The core is product. Around that, you would run the engineering team's operating rhythm and own the numbers that show whether customers are healthy.

The company is funded with $10M from Y Combinator, Strategic Cyber Ventures, Sorenson Capital and others, and is based in NYC.

Success milestones: within 30 days, shadow the CTO on every customer and planning call, review every discovery transcript from the last quarter, and ship a first fix using AI tools. Within 60 days, run cycle planning and release QA, get a first spec shipped by engineering, and have customer health flags live for every account. Within 90 days, own one product area end to end, take the CTO out of the weekly support loop, and own the engineering priorities doc.

Responsibilities

• Do customer discovery and review calls, then turn what you learn into prioritized specs.
• Carry features from definition through launch and into adoption.
• Prototype fixes, internal tools and integrations with AI coding tools, and ship in days what used to take a sprint.
• With the CTO, run cycle planning and the priorities doc, and keep Linear accurate.
• Own release readiness: QA checklists, dogfooding, and the decision on whether a release ships.
• Define and track new-user retention, stickiness and account health on the analytics dashboard, build warning flags for at-risk accounts, and run projects to fix lagging metrics.
• Triage support escalations, follow up on post-call action items, and handle the technical side of demos and trials.

Requirements

• Build with AI tools such as Claude Code or Cursor, and have shipped real work that way. What you can build matters more than years on a resume.
• Have shipped something to real users, such as a startup you founded, a product built on a small team, or customer work as a forward deployed or solutions engineer.
• Read code, debug a failing integration, and hold your own with engineers. A formal CS degree is not required.
• Write clearly enough that a customer's IT lead and your engineers act on the same document.
• Learn fast, seek feedback and take ownership. You should be comfortable running a company someday.
• Experience: 2+ years.
• U.S. citizenship is required because the role works inside customer environments subject to export controls.
• Nice to have: a startup of your own, or a side project that real people use. No government or GovCon background is needed; the domain will be taught to you.
• Don't meet every qualification? Apply anyway. The company values self-starters who love to learn.

Conditions

Work in person in New York City four days a week.

Visa: US citizen/visa only.

Hiring takes about two weeks: a founder conversation, a product interview built on a real customer case (bring your AI tools), and a half-day onsite.

Benefits

• Health coverage: medical, dental and vision.
• 401(k) plan.
• Generous PTO.
• High ownership: the company hires capable people and stays out of their way.
• Deep exposure to AI agents, in the product and in how the team works.
• Direct work with customers who get real value from the product.
• An in-person team in NYC.