Director of Product Design

Who we areHelp Scout started in 2011 with a simple premise: support software should treat customers like people, not tickets. 3+ billion conversations later, more than 10,000 companies use Help Scout to grow relationships with customers of all types, from clients to patients and beyond.

Now we’re in a new chapter: not only building AI that gives teams more space to focus on the customer experience, but also reimagining how we operate in an AI-native world. That means shipping and learning faster, without compromising on craft. Great work here carries a strong opinion and sweats the details, regardless of the tools we use to drive it.

We’ve been a fully remote team since day one, with 120+ teammates now all over the world. It’s a culture where you’ll be trusted to take ownership, stay curious, and raise the quality of work around you. It comes with clear expectations and a team that will push you to do some of the best work of your career.

If that kind of challenge gives you energy, we’d love to meet you.

Your ImpactHelp Scout has earned something most software companies never get: genuine trust. 10,000+ businesses use us because we've always believed that customer relationships are the business, and that every interaction should feel like it came from someone who cares. That trust took a decade to build, and now it's the foundation for something bigger.

A lot of that trust is design. When customers tell us why they picked Help Scout over the alternatives, and when they recommend us to someone else, the reason they give most often is that it is easier to use and it feels better to work in. That's why our top source for new customers comes from human and agent referrals. Our user experience is one of the strongest advantages we have, and as Director of Product Design you'll be directly accountable for keeping our quality high as we accelerate our growth.

About the role- Lead our product design team as a player/coach. Manage and develop a small team of experienced product designers and stay close to the work through critique, design reviews, and occasional projects of your own. Your most senior individual contributors carry the most complex design problems; your job is to make sure the whole team's work meets the bar. Set clear expectations for craft and ownership and build a culture where critique and feedback make the work better.

• Turn great design judgment into something that scales. Own the design principles, standards, guardrails, and decision record that make a Help Scout experience feel like Help Scout, so designers, engineers, and AI agents can create high-quality experiences with more speed and autonomy. Your most senior designers author the interaction models and product patterns that sit underneath them.

• Be accountable for our design system as a product. Set the priorities and resourcing for the Help Scout Design System (HSDS), drive its adoption across Product and Engineering, and make it useful and legible to both people and machines, working with the designer who serves as its technical lead for architecture, patterns, and Figma/code parity.

• Own how AI shows up in our product. AI is every designer's job, not one person's. You are accountable for Help Scout's point of view on trustworthy AI experiences: how AI communicates, gives people control, handles mistakes, and moves from assisting customers to acting on their behalf. Your most senior designers lead the design direction and patterns; you make sure that point of view is adopted and applied consistently by every designer, and that it evolves with the product.

• Evolve how design gets done as AI accelerates delivery. Own the operating model: workflows, tooling standards, design debt, how design works with Product and Engineering, and how the capacity AI frees up gets reinvested. Decide which of the practices the team pilots (code prototyping, AI-assisted workflows) becom...