Senior/Staff Product Designer

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 $138M from Accel, Caffeinated Capital, Friends & Family Capital, Point72 Ventures, General Catalyst, and In-Q-Tel.

Job Description

We’re hiring a Senior/Staff Product Designer to own key product/design areas for Twenty’s mission-critical software and help shape the product experience as we scale.

This person will be a senior individual contributor who partners closely with product managers, engineers, mission/domain experts, and company leadership. They will work in ambiguous product areas, understand complex user workflows, turn messy requirements into clear product experiences, and help raise the quality bar for how Twenty designs and ships software.

This is a hands-on ownership role for a product-minded designer who can move from problem framing to interaction design to polished execution. The right person is comfortable working with technical products, expert users, and fast-changing priorities. They can think strategically, sweat the details, and collaborate deeply with PM and engineering.

What You’ll Do

• Own design for important product areas from discovery through shipped product.

• Translate ambiguous customer, mission, and product needs into clear workflows, prototypes, interaction models, and product experiences.

• Partner closely with PMs, engineers, and domain experts to shape product direction and make thoughtful tradeoffs.

• Simplify complex technical workflows into usable interfaces for expert users.

• Use customer/user insight, product judgment, and business context to inform design decisions.

• Create high-quality flows, wireframes, prototypes, and visual designs.

• Own and evolve early design patterns, product experience principles, and reusable components as the product grows.

• Communicate design rationale clearly to cross-functional partners and leadership.

• Operate with high ownership in a fast-moving, high-ambiguity environment.

What We’re Looking For

• Experience designing complex B2B, enterprise, developer, security, defense, data, AI, or technical products.

• Strong product judgment: you can identify the real problem, make tradeoffs, and prioritize when the path is unclear.

• Excellent interaction design and systems-thinking skills.

• Strong visual/product craft, with the ability to move quickly without losing quality.

• Comfort partnering deeply with PM and engineering.

• Ability to challenge assumptions, explain rationale, and influence direction without relying on authority.

• Comfort working with technical, expert, or operational users.

• Clear, crisp communication with engineers, PMs, executives, and users.

• Ability to operate in ambiguity, high stakes, and fast-changing product conditions.

Nice to Have

• Experience in cybersecurity, defense, intelligence, developer tools, data platforms, AI/ML products, or workflow-heavy enterprise software.

• Experience designing for analyst, operator, investigation, command-center, or human-in-the-loop workflows.

• Experience at an early-stage startup or as an early design hire.

• Experience building design systems or product patterns from scratch.

• Familiarity with AI-assisted workflows or complex data-heavy interfaces.

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.