Director of Product Design

Who we are

Help 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 Impact

Help 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) become the standard way we work. Your most senior designers shape how AI fits into the design process itself; you make sure that guidance becomes how the team actually works.

• Help shape product direction alongside Product and Engineering. As a member of our Experience Leadership Team (XLT), bring design judgment, customer understanding, and a clear view of where design investment will have the greatest roadmap impact. Carry business context, constraints, and initiative outcomes back to the design team, and bring designers into the forums where direction for their work is being set.

• Decide where design capacity goes. Match designers to workstreams based on business priority. Decide who is embedded where, when someone shifts to a higher-priority problem, and when designers move from horizontal work to a deep, time-bound embed in a single workstream.

• Partner with the Brand Design team in our GTM organization to help ensure design cohesion between marketing and in-app product experiences.

About you

• You're an experienced product design leader who still loves the work. You bring 10+ years in product design, including 3+ years managing designers, and have been accountable for the experience of a product, as well as the people creating it.

• You have exceptional product and design judgment. You care about craft in a way that shows up in the details, can clearly articulate why an experience works, and have experience making complex B2B software feel simple and intuitive.

• You know how to scale great product design. You've built or meaningfully evolved a design system that teams genuinely adopted, and you know how to translate taste and judgment into principles, patterns, and systems others can apply.

• You have a strong point of view on AI and the future of product design. You use AI throughout your own design practice and think deeply about both how AI changes the way products are designed and how to create AI experiences customers can trust.

• You know how to lead senior individual contributors. You've managed principal or staff-level designers, given them real scope, and made them more effective without competing with them for the work.

• You're a deeply cross-functional product leader. You're technically fluent enough to earn the trust of engineers, comfortable using data and customer research to inform your decisions, and skilled at partnering with Product and Engineering on difficult tradeoffs.

• You're an exceptional communicator and remote leader. You make your thinking visible through clear writing and direct feedback, treat words as part of the product experience, and know how to build trust, alignment, and a strong design culture on a distributed team.

Who you'll work with

• Chief Product Officer. You report to the CPO and partner closely with them.

• Chief Revenue Officer. You partner on design cohesion between marketing and product, and on how design shows up in GTM.

• VP of Engineering. You collaborate on how design and engineering work together, on the design system, and on AI-assisted delivery.

• Principal Designer. Our most senior individual contributor reports to you and leads product design direction across workstreams, the design direction for AI experiences, and the technical shape of HSDS.

• Product Designers. A small team of experienced designers embedded in our product workstreams.

Note: This role is open to US-based applicants only.

Company values

Happy to Help

Help is in our first name! We show up for each other — not out of obligation, but because we’re invested in the team’s collective success. We share knowledge freely, lead with generosity, and practice empathy with our teammates, customers, and community.

Craft over Convention

Our success relies on the quality and craft of the work we put into the world. The status quo simply won’t work. So we insist on narrow focus, sweating every detail, and relentless pursuit of customer delight.

Progress not Perfection

Achieving our true potential — collectively and individually — requires constant progress and forward momentum. By creating a culture of curiosity and openness, we aim to create a safe space for mistakes, the ability to identify them quickly, and use them to get better.

Own the Outcome

Own the outcome means taking full responsibility for the results of your work, decisions, and contributions. It reflects a mindset of accountability, proactiveness, and follow-through. If you “own the outcome,” you don’t just complete tasks, you ensure your work leads to meaningful results, and take initiative to solve problems rather than passing them along.

Read more about how we define, share, and live these values here.

Benefits And Perks

• Competitive salary and an internal, transparent salary formula based on market data

• Flexible time off – you choose the holidays and vacations that make sense for you

• 12 weeks of fully paid parental leave for all new parents, including adoption and foster care

• A home office stipend to help you get set up and productive

• A co-working stipend up to $300 a month if you choose to work out of your house

• A yearly professional development stipend of $1,800 to help you grow in your craft

• If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents.

Hiring Guidelines:

All roles at Help Scout are fully remote. Some positions have specific location requirements. For roles outside the U.S. and Canada, we work with teammates as independent contractors under country-specific agreements.

We do not sponsor visas. Teammates must already be authorized to work from their home country.

We are an equal opportunity employer and are committed to building a company that embraces and celebrates diversity and inclusion. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, or disability status. We have read the studies and understand that diverse teams build better products, bring more perspective to the table, contribute to a company’s financial success, and help foster a more inclusive environment for all employees, but the bottom line is that it's the right thing to do.

To provide you with the best experience, we can support you with accommodations or adjustments at any stage of the recruitment process. Simply inform our recruitment team during your conversation with them.

A note on the use of AI in our interview process

While we understand that AI is an important tool in a modern skillset, we ask that you do not utilize AI assistants live on our interviews. Of course, use any tools you need to prepare! But we'd like for you to have a real human-to-human conversation with our team.

On our end, we utilize a platform called Brighthire as a notetaker and review tool to ensure a fair and transparent hiring process.

Beware of scammers! All legitimate communication from Help Scout regarding your application will come directly from an @helpscout.com email address and through our applicant tracking system, Ashby. We will never ask for personal financial information or conduct interviews outside of these official channels.