Controller (Relocation to NYC or DC)
About The Company
Twenty Technologies is an industrialized offensive cyber operations firm founded in 2024. We aim to make our adversaries think twice about attacking us, ensuring American and allied primacy in cyberspace. Headquartered in Arlington, Virginia, Twenty has raised $138M from leading investors and is headquartered in New York City or Washington, DC.
Role Summary
As our first Controller, you will lead the accounting department, developing a sophisticated, high-velocity finance function from the ground up. You will collaborate with external partners to ensure peak efficiency in our financial operations.
Core Responsibilities
Own Accounting and Financial Operations: Lead all accounting functions, from annual to day-to-day workflows, ensuring accuracy, efficiency, and timeliness. Build for scalability by automating and optimizing processes.
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 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 and trust with all employees.
Special Projects: Support a range of initiatives, including real estate planning, variable compensation analysis, cash management policies, and contracting.
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.