Senior​/Product Designer

hackajob is collaborating with Twenty to connect them with exceptional professionals for this role.

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 ((Use the "Apply for this Job" box below).) 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, Point
72 Ventures, General Catalyst, and In‑Q‑Tel.

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.

• 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.

• 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.

• 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.

• 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…