Controller

About the Company

America is under sustained cyber attack. Our adversaries infiltrate our networks, steal our IP, and degrade the digital infrastructure that modern life runs on. They’ve learned—correctly—that those attacks rarely produce consequences.

Twenty was founded to change that, by making our adversaries think twice before they attack us. Our vision is American and allied primacy in cyberspace—a future where they cannot contest us, deterrence is assured, and the free world remains secure.

Founded in 2024, Twenty Technologies (www.twenty.io) industrializes offensive cyber operations for the U.S. and its allies. Headquartered in Arlington, Virginia, Twenty has raised $38M from Caffeinated Capital, General Catalyst, and In-Q-Tel.

This role is based full-time in either our New York City office or our Washington, DC headquarters. Candidates currently based in the San Francisco Bay Area must be willing to relocate to NYC or the Washington, DC area.

Role Summary

As our first Controller, you will be the foundational leader of our accounting department. This is a "player-coach" role designed for someone who wants to architect a sophisticated, high-velocity finance function from the ground floor.

You will lead the development of our internal systems, controls, and automated workflows, ensuring we are navigating hypergrowth optimally. A key part of this role involves collaborating with and overseeing our external partners to ensure our financial engine is running at peak efficiency. You will anticipate the requirements for scale and leverage AI-native tools to build a modern, lean, and highly accurate department.

What You'll Own (Core Responsibilities)

• Own Accounting and Financial Operations: Lead all accounting functions, from annual to day-to-day workflows, ensuring accuracy, efficiency, and timeliness. You will own the procure-to-pay lifecycle.

• Build for Scalability: Identify, propose, and implement solutions to automate and optimize processes. Work with our team to maintain (or reduce) overhead requirements, even as transaction volumes 10x.

• Future Audit Readiness: Prepare Twenty for future audits by building the required roadmap and timing of all necessary requirements.

• External Management: Manage and build relationships with all external partners, including tax, bookkeeping, vendors, government partners, and auditors.

• Systems Optimization: Explore and implement tools like Ramp AI and API connections between internal systems to streamline workflows.

• People & Policy: Develop internal processes, such as expense and procurement policies; build strong relationships with company leaders, as well as trust with all employees.

• Special Projects: Support a range of initiatives, which may include real estate planning, variable compensation analysis, cash management policies, and contracting.

• Treasury: Monitor corporate cash balances and manage treasury movements to ensure the company remains optimized across liquidity and yield.

• Cross-Functional Support: Step outside the normal job description to own key workflows that help a cross-functional team scale rapidly—e.g., assisting with Sales Ops, Legal, HR, and Office operations.

Qualifications

• Accounting Experience: 8+ years of accounting experience, including time in Big 4 (or equivalent) audit and high-growth technology startups.

• Government Contracts Experience: Experience with DCAA compliance and government contracts.

• Credentials: Current or former CPA is favored, but not required.

• Execution-Oriented: You believe that what sets high-performing teams apart is their ability to execute.

• Highly Detail-Oriented: You believe that formatting is a valuable tool for cross-functional communication, not a burden. You sweat the details because you know they matter.

• Concise Communication: Ability to distill information for executive audiences.

• Prioritization: You understand the operational realities of a high-growth startup, knowing when speed must beat perfection and when a task is more efficient handled manually.

• Financial Systems Expertise: Experience implementing and managing modern financial systems (e.g., ERP, spend management, payroll platforms) is required. Mastery with Excel and Google Sheets.

• Self-Propelled: You know what an excellent accounting function looks like, identifying gaps and filing them without waiting for instructions. You thrive in the unstructured environment of an early-stage company.

• Future-Oriented: You are eager to explore and implement new technologies (e.g., AI workflow/productivity tools).

Nice to Have

• Defense or Cyber Background: Prior background in the defense technology or cybersecurity industries, or similar revenue / expense structures.

• Specific Systems: Familiarity with Campfire and Ramp.

• Sense of Humor: Nano Banana image generation ability.

Benefits
What's on the table:

• Health. Medical, dental, and vision plan options. Life / AD&D, disability coverage options.

• Family. Paid parental leave for eligible full-time employees. 12 weeks for birthing parents, 4 for non-birthing parents, 6 weeks for adoptive, foster, or intended parents through surrogacy.

• Vacation. Paid holidays and flexible PTO. Take what you need.

• Retirement. 401(k) with pre-tax and Roth options. HSA/FSA options, dependent care FSA.

• At the office. Commuter benefits. On-site garage parking. Bike storage. Building fitness center. Desk setup stipend.

Benefits vary by location, role, and eligibility. Full plan details provided during the interview and offer process.

If this role sounds like you, apply and share with us your interest.

Some positions may require eligibility to obtain a U.S. Government security clearance. Any clearance requirement will be listed in the role description.

Twenty is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, veteran status, disability, or any other protected status.

If you need a reasonable accommodation during the hiring process, let us know and we will work with you.