Director of Product Design

Help Scout • ,

4d • $226,000 - $242,000 • Remote

About The Position

Help Scout is seeking a Director of Product Design to lead their product design team. This role involves managing and developing a team of experienced product designers, providing critique and design reviews, and occasionally taking on design projects. The Director will be responsible for maintaining high quality standards, setting clear expectations for craft and ownership, and fostering a culture of constructive feedback. They will also own the design principles, standards, and decision records that define the Help Scout experience, ensuring consistency across designers, engineers, and AI agents. A key responsibility is managing the Help Scout Design System (HSDS) as a product, setting priorities, driving adoption, and ensuring its usability for both humans and machines. The role also involves owning Help Scout's approach to trustworthy AI experiences, including how AI communicates, provides control, handles errors, and acts on behalf of customers. The Director will evolve the design operating model, including workflows, tooling, and how design collaborates with Product and Engineering, especially in leveraging AI to accelerate delivery. As part of the Experience Leadership Team (XLT), they will influence product direction, bring design judgment and customer understanding to roadmap planning, and communicate business context back to the design team. They will also be responsible for allocating design capacity to workstreams based on business priorities and partnering with the Brand Design team to ensure design cohesion between marketing and product experiences.

Requirements

• 10+ years in product design.
• 3+ years managing designers.
• Accountability for the experience of a product and the people creating it.
• Exceptional product and design judgment.
• Ability to articulate why an experience works.
• Experience making complex B2B software feel simple and intuitive.
• Experience building or meaningfully evolving an adopted design system.
• Ability to translate taste and judgment into principles, patterns, and systems.
• Strong point of view on AI and the future of product design.
• Experience using AI throughout personal design practice.
• Experience creating AI experiences customers can trust.
• Experience managing principal or staff-level designers.
• Technically fluent enough to earn the trust of engineers.
• Comfort using data and customer research to inform decisions.
• Skilled at partnering with Product and Engineering on difficult tradeoffs.
• Exceptional communicator and remote leader.
• Ability to make thinking visible through clear writing and direct feedback.
• Ability to build trust, alignment, and a strong design culture on a distributed team.
• US-based applicants only.

Responsibilities

• Lead and manage a small team of experienced product designers.
• Provide critique, design reviews, and occasional design projects.
• Ensure the team's work meets high quality standards.
• Set clear expectations for craft and ownership.
• Build a culture where critique and feedback improve the work.
• Own and scale design principles, standards, guardrails, and decision records.
• Own the Help Scout Design System (HSDS) as a product, setting priorities and driving adoption.
• Define Help Scout's point of view on trustworthy AI experiences in the product.
• Ensure AI experience guidelines are adopted and consistently applied by designers.
• Evolve the design operating model, including workflows, tooling, and collaboration with Product and Engineering.
• Decide how AI-generated capacity is reinvested.
• Shape product direction alongside Product and Engineering as a member of the Experience Leadership Team (XLT).
• Allocate design capacity to workstreams based on business priority.
• Partner with the Brand Design team to ensure design cohesion between marketing and product experiences.

Benefits

• Competitive salary and an internal, transparent salary formula based on market data
• Flexible time off
• 12 weeks of fully paid parental leave for all new parents, including adoption and foster care
• A home office stipend
• A co-working stipend up to $300 a month
• A yearly professional development stipend of $1,800
• Top tier health insurance for you and your dependents (if in the U.S. or Canada)

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed