SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Help Scout is a customer support platform used by 10,000+ companies to manage customer relationships. Founded in 2011, the company has processed 3+ billion conversations and operates as a fully remote team of 120+ people worldwide. The company is entering a new chapter focused on AI-native product development while maintaining its core commitment to craft and customer experience.
As Director of Product Design, you will lead Help Scout's product design function with accountability for both the team and the product experience. Your responsibilities include:
**Team Leadership & Culture**: Manage and develop a small team of experienced product designers, staying close to the work through critique, design reviews, and occasional hands-on projects. Set clear expectations for craft and ownership, building a culture where feedback elevates quality.
**Design Systems & Standards**: Own the design principles, standards, guardrails, and decision records that ensure consistency across Help Scout's experience. Scale design judgment through documented patterns and interaction models that enable designers, engineers, and AI agents to work with autonomy.
**Design System Product**: Set priorities and resourcing for the Help Scout Design System (HSDS), drive adoption across Product and Engineering, and ensure it serves both people and machines with clear architecture and Figma/code parity.
**AI in Product Design**: Lead Help Scout's point of view on trustworthy AI experiences—how AI communicates, provides control, handles mistakes, and transitions from assisting to acting on behalf of users. Ensure this perspective is consistently applied across the design team.
**Operating Model Evolution**: Own how design processes evolve as AI accelerates delivery. Manage workflows, tooling standards, design debt, and cross-functional collaboration with Product and Engineering. Pilot and standardize new practices (code prototyping, AI-assisted workflows).
**Product Strategy**: Serve on the Experience Leadership Team (XLT) to shape product direction alongside Product and Engineering leadership. Bring design judgment and customer understanding to roadmap decisions, and communicate business context back to the design team.
**Resource Allocation**: Match designers to workstreams based on business priority, decide embedding strategies, and reallocate capacity as priorities shift.
**Brand Cohesion**: Partner with the Brand Design team in GTM to ensure design consistency between marketing and in-app experiences.
You report to the Chief Product Officer and collaborate closely with the Chief Revenue Officer, VP of Engineering, and a Principal Designer (your most senior IC).
**Requirements**
- 10+ years in product design, including 3+ years managing designers
- Proven accountability for both product experience and the people creating it
- Exceptional product and design judgment with attention to detail; ability to articulate why experiences work
- Experience making complex B2B software feel simple and intuitive
- Track record building or meaningfully evolving a design system with genuine team adoption
- Strong point of view on AI and its impact on product design; active use of AI in your own practice
- Experience leading senior individual contributors (principal or staff-level designers) with real scope
- Deep cross-functional product leadership skills; technical fluency to earn engineer trust; comfort with data and research
- Exceptional communication and remote leadership abilities; clear writing, direct feedback, ability to build trust and culture on distributed teams
- US-based (role restricted to US applicants)
- Already authorized to work in home country (no visa sponsorship)
