Finance and Operations Generalist

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 our Arlington, VA headquarters. Candidates currently based in NYC must be willing to relocate to the Washington, DC area.

Role Summary

The Finance and Operations team focuses on some of Twenty’s most critical business problems with a high degree of visibility into the entire organization. The team is responsible for annual planning, resource allocation, performing financial analysis, and acting as a business partner with leaders across the company. This role requires someone who is highly analytical and strategic, a great communicator, a structured problem solver, and level-headed when faced with ambiguity.

This role is ideal for a former banker, investor, or startup finance operator who wants to skip business school and jump into a high-velocity generalist seat from the ground floor. You are eager to stop spreading comps and start building a company.

What You'll Own (Core Responsibilities)

• The Model. Build and own Twenty's financial model end-to-end. Drive annual planning, the headcount ledger, board reporting, and the analytical engine the company uses to make decisions. When investors ask questions in the next fundraise, your modeling work is what helps answer them.
• FP&A & Reporting. Run semi-annual budgeting and ongoing headcount planning. Stand up the reporting infrastructure that gives every function visibility into how it's actually performing. Translate the financials into something team leaders can act on.
• Fundraising & Investor Relations. Partner with the Founders and VP Finance on the next fundraise. Build the data room and own diligence. Between rounds, own monthly executive updates and quarterly board reporting.

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• The Operating Cadence. Run the systems that keep a company moving: compensation design, offer generation, performance structure, and spend policies.
• Special Projects. Some examples are real estate, market research, vendor strategy, software procurement.
  
  

Who You Are

• 1–5 years in investment banking, private equity, or strategic finance at a top-tier startup.
• Mastery with Excel and Google Sheets. You can build a highly legible three-statement model, and you can layer in scenario modeling to answer urgent questions.
• Detail-obsessed. You believe formatting is a tool for cross-functional communication, not a chore. You sweat the small stuff because small mistakes can compound.
• High horsepower. You dive in head first, whether it’s a one-page memo for the CEO, a slide for the Board, or an offer package for a new hire.
• Urgency. You don't wait for directions—you figure things out. You create your own urgency, whether it is because the status quo frustrates you or because you see the path to a better end state.
• Generalist by instinct. You enjoy a wide problem space. You apply first principles across finance, hiring, contracts, and ops because the underlying skill is the same: think clearly, move fast, get to the answer.

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• In-person builder. You want to spend your career around kind and smart people—refining your craft while advancing a critical mission.
  
  

Nice to Have

• Industry Experience. Prior background or interest in software, AI, cyber, defense, or intelligence.
• AI Pilled. Daily ChatGPT, Claude, or Gemini user. Use Claude Code or Cowork, Rogo, Hebbia, or equivalent AI tools. You see agents as the way to automate routine tasks and as the future of work.
• 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.