Controller (Relocation to NYC or DC)
About The Company
Twenty Technologies is an innovative company founded in 2024, dedicated to making the United States and its allies dominant in cyberspace. We aim to deter adversaries by making them think twice about attacking us. Headquartered in Arlington, Virginia, Twenty has raised $138M from leading investors including Accel, Caffeinated Capital, Friends & Family Capital, Point72 Ventures, 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 based in the San Francisco Bay Area must relocate to either location.
Role Summary
As our first Controller, you will lead the accounting department, ensuring accuracy, efficiency, and timeliness in all accounting functions. You will also collaborate with external partners to ensure optimal financial performance and develop internal processes and policies. This is a "player-coach" role designed for someone who wants to build a sophisticated, high-velocity finance function from the ground up.
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 increase.
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 filling 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
Health: Medical, dental, and vision plan 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.