Senior/Staff Product Designer

About the Company

Twenty was founded to change the landscape of cyber security. Our adversaries are constantly probing our digital infrastructure, stealing intellectual property, and undermining our defenses. We believe that by industrializing offensive cyber operations, we can deter these threats and ensure the security of the free world.

Founded in 2024, Twenty Technologies (www.twenty.io) is headquartered in Arlington, Virginia. We have raised $138M from leading investors including Accel, Caffeinated Capital, Friends & Family Capital, Point72 Ventures, General Catalyst, and In-Q-Tel.

Job Description

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

• 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 product managers, 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 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 product managers, 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 product managers and engineers.
• 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, product managers, 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

• 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.