Senior/Staff Product Designer

About The Company

Twenty Technologies (www.twenty.io) industrializes offensive cyber operations for the U.S. and its allies. Founded in 2024, Twenty has raised $138M from leading investors including Accel, Caffeinated Capital, Friends & Family Capital, Point72 Ventures, General Catalyst, and In-Q-Tel. Headquartered in Arlington, Virginia.

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 is a hands-on ownership role for a product-minded designer who can move from problem framing to interaction design to polished execution.

• 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 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

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.

Benefits vary by location, role, and eligibility. Full plan details provided during the interview and offer process.

Pay

TBD

Schedule

TBD