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TwentyTwentyArlington, VA

Senior/Staff Product Designer

Senior/Staff Product Designer owning key areas of mission-critical offensive cyber software at an early-stage startup. Translate complex technical and domain requirements into clear, high-quality interfaces and experiences for expert users; partner closely with PMs, engineers, and leadership in a fast-moving, ambiguous environment.

Salary not listed
On-site5+ YOEProduct Design

About the role

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 (12 weeks for birthing parents, 4 for non-birthing, 6 for adoptive/foster/surrogacy).
  • Vacation: Paid holidays and flexible PTO.
  • Retirement: 401(k) with pre-tax and Roth options. HSA/FSA options.
  • At the office: Commuter benefits, on-site garage parking, bike storage, building fitness center, desk setup stipend.
  • Benefits vary by location, role, and eligibility.

Skills

Interaction DesignSystems ThinkingWireframingPrototypingVisual DesignDesign SystemsProduct JudgmentUser WorkflowsFigmaUser Research

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