Staff Product Designer, Go-to-Market AI (Ontario)

POS-29684 

Location: Canada, Ontario - Remote, Flex, or Office

Join HubSpot’s Design Team

The Flywheel Product Line is an org focused on helping HubSpot grow faster by using AI to dramatically improve how we serve customers and how our GTM teams work. We're doing this across three core areas:

• First, we’re building an AI concierge that supports customers throughout their lifecycle - solving support issues, identifying their goals, unlocking underused features, and helping them get more value from HubSpot. This AI agent qualifies their needs, guides them toward more advanced capabilities, answers support queries, and recommends upgrades - all autonomously, and across multiple formats: chat, voice, real-time AI-generated video and more. It’s a huge design challenge, cutting across use cases, modalities, and interfaces, and it’s something very few companies have even come close to doing well.
• Second, we’re extending our core product with AI-first tools that radically improve how HubSpot’s go-to-market teams (support, sales, customer success) work. That means eliminating repetitive admin work, giving managers superpowers to coach and scale, and helping reps focus on the right leads and the right moments. This is where small UX decisions turn into massive business impact - improving efficiency here directly influences revenue at a multi-billion dollar scale.
• Third, we’re building dedicated experiences for HubSpot’s global partner ecosystem - agencies and consultancies who sell and implement HubSpot on our behalf. These partners drive over $1B in revenue annually. We’re both creating agentic AI experiences for partner-specific needs, and enabling these businesses with unique tools in HubSpot that help them grow faster and operate more efficiently. Their workflows are unique, and their impact on HubSpot’s growth is massive, making this a critical area of focus for Flywheel.

As a Staff Product Designer, you won’t be embedded in a single team or feature area. Instead, you’ll operate at the product line level, shaping the future across multiple domains. You’ll work 3-12 months ahead of delivery — exploring opportunities, prototyping bold ideas, and building narratives that influence leaders across R&D and GTM. 

This role is about vision, strategy, and influence at scale - working at the very edge of what’s possible in applied AI, defining what’s next for a $30B+ company.

Why Flywheel?

Come join us for a career-defining opportunity to:

• Shape the future of applied AI: Work on problems very few companies have even attempted - like building autonomous multi-modal, multi-usecase AI concierges, AI-first GTM tools, and new agentic experiences for our global partner ecosystem.
• Operate at massive scale: Even small improvements in this space drive hundreds of millions in revenue impact. The work you’ll do here will directly influence hundreds of thousands of HubSpot customers.
• Career-defining scope: You’ll operate at the “tip of the spear” for innovation, crafting ideas, prototypes, and narratives that will influence the C-suite and set direction for HubSpot’s future.
• Experiment & explore: Think of this role like an applied design innovation lab - rapid, unorthodox, and experimental. You’ll be encouraged to prototype, test, and push bold ideas, not follow a rigid process.
• Work on platform-scale initiatives: Tackle ambiguous, high-impact problems that span the entire HubSpot platform, requiring a broad perspective and a focus on unified outcomes.
• Leverage data & AI: Harness smart data, advanced automation, generative AI, and LLMs to create personal, intelligent, and connected customer experiences.

What You’ll Do

• Define the future: Explore, visualize, and prototype bold concepts that shape where HubSpot’s GTM should go 3–12 months out.
• Understand complex systems: Research problems, map incentives, and identify opportunities across customer, GTM, and partner ecosystems.
• Prototype to influence: Create high-fidelity prototypes (in Cursor, Lovable, V0, Figma etc) and concept visuals to make abstract ideas tangible and compelling.
• Shape the narrative: Craft stories and presentations that inspire alignment and buy-in from product, GTM, and executive leaders.
• Raise the bar: Uplevel craft quality across the org by modeling strong design work, offering feedback, and sharing thinking through crits, office hours, or mentoring.

What You’ll Bring To HubSpot

We’re not looking for a single mold of designer. You might be:

• A designer with deep AI fluency - able to design adoptable AI-first products and push the boundaries of what’s possible.
• A craft-driven designer with exceptional interaction and visual design skills who can turn complex ideas into beautiful, adoptable experiences.
• A systems thinker and influencer who excels at managing complexity, aligning stakeholders, and selling bold futures to diverse, opinionated audiences.

To succeed, you’ll need:

• A growth mindset - curious, experimental, and not tied to a single way of working.
• Strong skills in concept visualization and prototyping (from decks to vibecoded prototypes).
• Experience driving 0–1 or highly ambiguous product work.
• Comfort operating in spaces with multiple stakeholders, incentives, and nonlinear problems.
• Excellent communication skills, with the ability to tell compelling stories that influence strategy.

We’re hiring across levels! If you’re earlier in your career, check out our Senior Product Designer role.