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About The Position

Pencil is hiring a VP of Product Design to bring product design and UX into one function, establish a shared quality bar, and lead design across product squads. Designers will report to design while working within squads; squads own priorities and delivery, while design owns craft and sign-off. The role will build a strong design culture and raise the creative ambition of a product that has primarily been built for functionality. The VP will own review and adoption of Pencil’s existing design system, closing gaps and implementing it throughout the product. This includes bringing design tokens into code, creating a component library used by engineering, measuring adoption through shipped screens, and making the system the source used by AI coding tools. The role will also define how users brief, run, supervise, review, and approve work performed by agents, while ensuring the product serves both enterprise buyers who value governance and trust and practitioners who value speed and creative range. The role will establish how design works with product and engineering, including design review, pattern approval, and shared rituals. It will shape the team’s structure, levels, career paths, and hiring; partner with Marketing Design; bring design into discovery and customer research; and use post-launch reviews to assess outcomes. The VP will hire and lead design engineers and build accessibility into the design system. In the first 90 days, the role will meet designers and learn the product, squads, and customers; review the design system; ship a shared pattern across two features; and agree on design review and contribution practices with the CTO and product leads. By month six, high-use flows should work consistently across the product, with team structure, levels, and rituals in place. By month twelve, new features should ship on-system by default, including AI-built features, duplicated components should be decreasing, and customers should experience Pencil as one product.

Requirements

  • 10+ years of experience in product design.
  • 5+ years leading teams of designers, including other leads.
  • Experience building a design culture and inspiring designers.
  • Experience taking an existing design system and driving its adoption in a fast-moving B2B product, with evidence of adoption beyond the component library.
  • Experience with complex enterprise software, including workflows, permissions, review and approval, and dense data.
  • Regular use of AI tools in design and understanding of how coding agents affect design workflows.
  • Ability to work with engineering on tokens, component APIs, and front-end constraints.
  • Strong hands-on design craft and ability to improve screens directly.
  • Experience leading organizational change and earning the trust of teams that have worked without a design leader, including bringing existing leads along.

Nice To Haves

  • Experience designing AI or agent products.
  • Experience designing creative or marketing tools.
  • Experience leading teams across time zones.

Responsibilities

  • Bring product design and UX into a single design function with one quality bar, while designers work within product squads.
  • Inspire the design team and establish a culture of critique, shared rituals, and creative ambition.
  • Partner with product and engineering to ship features on time and in accordance with the design system, while raising the level of craft and delight.
  • Set design turnaround times, use AI tools and the design system to speed up design work, and track design timelines for squad planning.
  • Review the existing design system, address gaps, and implement it across the product, including tokens in code and a component library consumed by engineering.
  • Make the design system the source for AI coding tools and create written guidelines to keep AI-generated UI on-system.
  • Define interaction patterns for briefing, running, supervising, reviewing, and approving agent work.
  • Design for both enterprise buyers’ needs for governance, control, and trust and practitioners’ needs for speed and creative range.
  • Establish design review, pattern approval, and shared working rituals across design, product, and engineering.
  • Shape team structure, levels, career paths, and hiring.
  • Work with Marketing Design to align the product experience and brand.
  • Bring design into discovery, work with product research to ground design decisions in customer evidence, and use post-launch reviews to assess results.
  • Hire and lead design engineers who translate the system into code used by engineering and AI coding tools.
  • Build accessibility into the design system so features meet enterprise customer expectations.
  • In the first 90 days, learn the product, squads, customers, and team; review the system; ship one shared pattern across two features; and agree on design review and contribution practices with the CTO and product leads.
  • By month six, make the most-used user flows consistent and put team structure, levels, and rituals in place.
  • By month twelve, ensure new features ship on-system by default, reduce duplicated components, and help customers experience Pencil as one product.

Benefits

  • 25 days PTO plus public holidays, with a Flexible Time Off scheme.
  • Health insurance / private medical cover.
  • Monthly stipend toward wellness, fitness, and learning and development.
  • Remote work from anywhere in the employee’s home country.
  • Enhanced parental leave for parents through birth, adoption, or surrogacy.
  • Access to the Pencil office in The Shard, London for UK employees.
  • Flexible working hours.

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