Head of Product Design at Shakepay driving design quality and customer experience across products. Leading and mentoring design team to elevate financial services for Canadians through innovative solutions.
About the role
- Lead Product Designer shaping user experiences for Zipline, a SaaS company in retail and logistics. Oversee design strategy and execution for complex, multi-phase initiatives.
Responsibilities
- Own design strategy and execution for the Operate pillar across complex, multi-quarter initiatives spanning task management, compliance workflows, and operational communication.
- Design elegant, intuitive solutions for multi-step workflows, creating new patterns and interaction paradigms where existing ones fall short.
- Make significant contributions to design system strategy and evolution, identifying opportunities for new reusable platform patterns.
- Consistently deliver work at a high level of polish—creating interfaces that simplify complexity without sacrificing depth.
- Adapt prototype fidelity to situational needs, using prototypes to inspire, validate, and align as much as to hand off.
- Define design strategy collaboratively with cross-functional partners, shaping problem definition and approach—not just execution.
- Identify new problems and opportunities for the team to solve, and define success metrics for major initiatives.
- Plan, conduct, and synthesize qualitative and quantitative research that deeply understands user motivations and business goals.
- Champion the user perspective across the product area and influence cross-team priorities based on research and insight.
- Bring design thinking to roadmap discussions and help the team make better tradeoff decisions.
- Build consensus around design decisions across multiple teams and stakeholders, especially during ambiguous or high-stakes moments.
- Lead design critiques that give high-quality, actionable feedback and elevate the craft of the team.
- Mentor and coach senior designers, helping them grow their skills and navigate complex challenges.
- Communicate design vision and rationale persuasively to leadership, facilitating productive conversations that build design credibility across the organization.
- Partner closely with Engineering on technical feasibility and implementation strategy, and identify design opportunities that drive business value.
Requirements
- 7+ years of product design experience, with a proven track record of owning significant product areas and shipping complex, high-impact features across multiple quarters.
- A portfolio that demonstrates mastery of interaction and visual design craft, systems thinking, and the ability to simplify genuinely complex problem spaces.
- Experience working in cross-functional agile teams and shaping product strategy and roadmap priorities alongside Product and Engineering partners.
- Experience designing AI feature sets and integrating AI-powered capabilities into product experiences.
- Deep fluency in user research—both qualitative and quantitative—and a proven ability to package findings into clear design direction that influences the broader team.
- Outstanding communication and storytelling skills; you can articulate complex design concepts persuasively to leadership and build alignment during hard conversations.
- Demonstrated ability to mentor senior designers and lead design critiques that improve team output.
- Expert-level proficiency in Figma and modern prototyping tools.
- Comfort operating in evolving or undefined problem spaces—you can bring structure without waiting for clarity to be handed to you.
- Bonus points for: experience with compliance or audit workflows, operational or enterprise product design, or AI-powered conversational interfaces.
Benefits
- Remote-first culture: Join a high performing, fully remote team and work where you're comfortable
- Stock Options: Get meaningful ownership in a fast-growing, venture-backed company shaping the future of retail.
- Time off: We believe rest fuels great work. Our flexible time-off policy gives you the freedom to take the breaks you need, when you need them—whether it's a long weekend or a well-deserved vacation. We'll also give you a monthly coffee-shop stipend to switch up your workspace and get inspired outside the office. And when you've been with us for five years? You'll earn a fully paid one-month sabbatical to truly unplug and reflect—we call it a thank-you for your impact and dedication.
- Benefits: World-class medical, dental, and vision policies.
- Team Connection: Annual company off-sites in fun locations. We've done New York, Costa Rica, Whistler, Palm Springs, San Diego, and Mexico City.
- Volunteering: Every quarter, Zipliners get a paid day off to volunteer for a nonprofit of their choice.
- Learning: We support continuous learning and provide unlimited access to our Udemy Business account
- Great humans, great work: Work with kind, collaborative teammates who care about doing meaningful work and making a real impact. We value diversity of all kinds and are committed to building a diverse and inclusive workplace where we learn from each other. We are an equal opportunity employer and welcome people of all different backgrounds, experiences, abilities, and perspectives.
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