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.

About the Role

High-growth startups are fluid, fast, and demanding. Before specializing, the best way to learn how a business runs is to build its foundational infrastructure. We're looking for a sharp, mature new graduate to join us as our first Operations Associate: someone who thrives in ambiguity, learns fast, and wants real ownership from day one.

This is a two-year program. We can’t foretell where it will lead you. You won't have a neatly defined career ladder or a single job function. What you will have is front-row access to how an early-stage company actually operates — across finance, HR, legal, recruiting, and the day-to-day of running an office. We'll invest in you, and we expect the same in return.

Candidates who distinguish themselves here will find new doors opening inside the company. We're also genuinely happy to support alumni who want to pursue graduate school or other opportunities after the program. We want this to be your launchpad.

What You'll Work On

Your portfolio will span the full operational backbone of the company. No two weeks will look the same.

• Finance & Accounting Contribute to ad hoc financial analyses and take on urgent projects like scoping new office expansion. Set up and maintain spend programs, process reimbursements, and help enforce financial policies as we build out our accounting infrastructure.

• HR & People Operations Own the new hire onboarding experience end-to-end — the workflows, the paperwork, the procedural steps. Become the go-to resource for benefits and policy questions. Help us build the kind of onboarding that makes people glad they joined.

• Recruiting Coordination Ensure every candidate who walks through our door has a great experience. Coordinate on-site interviews, greet candidates, book travel, and process candidate reimbursements.

• Office & Facilities Help furnish and set up our offices, configure A/V, prep for meetings, and greet guests. Keep operations running smoothly so the rest of the team can focus on their work. No task is too small to ensure that our workspace is humming.

• Legal Operations Support vendor and contractor negotiations, process NDAs and agreements, and help maintain our contracts workflow. Build a general understanding of legal operations in a growing business.

• Executive & Team Support Help run our biweekly all-hands, support team events and offsites, and step in wherever leadership needs an extra hand to execute.

Who You Are

• Recent Graduate: Holds a Bachelor’s or Master’s degree. All disciplines are welcome; a track record of high achievement and leadership is what matters most.

• Relentless Execution: You possess an extreme bias for action. No task is too small, too strategic, or too messy—you take immense pride in flawless operational delivery.

• High Emotional Intelligence (EQ): Exceptional verbal and written communication skills. You can seamlessly interface with a candidate, an executive, a vendor, or a board member.

• Obsessive Organization: You thrive in ambiguity by creating structure. You naturally track deadlines, balance 15 things at once, and never let a ball drop.

• Technical Aptitude: Quick to master modern tech stacks (SaaS tools, A/V equipment, spend platforms, and collaboration suites).

Nice to have:

• Coursework or Internship experience in business, operations, finance, or law

• Familiarity with productivity and collaboration tools such as Google Workspace, Notion, Airtable, or similar platforms.

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.