Lead Product Designer, Operate

HighlightTA is the on-demand talent team for Zipline.

About Zipline

Zipline is a well-funded, rapidly growing SaaS company transforming how frontline teams work. We empower the world’s leading brands across retail, healthcare, logistics, and beyond to connect, align, and inspire their employees- from headquarters to the front lines. Our customers consistently give us best-in-class NPS and CSAT scores, and they rave about how Zipline makes their teams’ lives easier and their businesses more effective. We’re also a fully remote company, with passionate employees across the U.S., Canada, and around the globe.

About the Role

At Zipline, getting work done on the front lines is anything but simple. Store associates juggle tasks, compliance requirements, and a constant stream of communication from HQ—often under time pressure and on a small screen. Our Operate pillar is the engine that keeps it all moving: it's where task management, compliance workflows, and operational communication come together to help frontline teams execute with clarity and confidence.

As a Lead Product Designer on the Operate team, you'll own the design strategy for complex, multi-phase initiatives and set the UX direction for a significant product surface. You're a sought-after design expert who proactively identifies and drives solutions—someone who shapes product direction through deep user understanding, builds alignment across stakeholders, and raises the bar on craft for the designers around you. You balance hands-on IC work with design critique leadership, mentoring senior designers, and influencing roadmap and strategy as a true cross-functional partner.

What You’ll Do

Craft & Execution

• 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.

Strategy & Customer Focus

• 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.

Leadership & Collaboration

• 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.

What We’re Looking for

• 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.

Compensation

At Zipline, we're committed to paying our team fairly, transparently, and in a way that supports growth. This role has a minimum annual salary within Canada of $134,607 CAD and a maximum of $201,914 CAD.

The broad salary ranges reflect the growth someone will experience in the role—from developing skills to reach expertise within their career level. We’ve found that hiring team members with the expectation of being accomplished in the role sets them up for success, which for this position within the Canadian band is $148,435 CAD. Salaries below this point typically reflect someone with potential but still building the necessary skills, while salaries above are for individuals already excelling in the role, with a deep understanding of Zipline’s impact on customers, product, and company.

At Zipline, you’ll continue to have career development conversations with your manager to ensure your compensation grows as you advance.

Our salary ranges are determined by market, factoring in our revenue and employee size, paying competitively at the 75th percentile. In higher cost of living markets, we apply 5-10% multipliers on our ranges, depending on the location, to maintain competitive compensation and reflective of the increased expenses our team members face in those areas. While we primarily hire in Canada and the USA, we are a global employer, and all hiring regions will use the same methodology to determine fair and transparent pay.

Transparency is key to building trust in our compensation process. To better understand how this range is determined, we encourage you to ask as many questions as you'd like about compensation during the interview process to ensure clarity and confidence


What's in it for you

• 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.

Want to learn more about how we work?

We may be remote, but we're anything but disconnected. Zipline is a thriving, dynamic team spread across the globe—collaborating, innovating, and having a blast along the way.

Zipliners work from all over—vans, boats, Airbnbs, and everything in between. No office? No problem. Our culture still feels like one big hug.

Even though we're distributed, we make space to connect—whether it's our weekly all-company social or gathering in person at our yearly retreats. We're building something meaningful together, and we're glad you're considering being a part of it.

We can't wait to meet you!

How We Hire

We use AI tools to support our recruitment process, including helping us organize applications and identify early matches based on role criteria. That said, every rejection decision is made by a human. We encourage candidates to apply authentically and avoid relying solely on AI-generated responses, especially during interviews.

This opportunity is offered through HighlightTA, the on-demand talent team supporting Zipline’s growth.

Connect with us and learn more:
Zipline on Linkedin
HighlightTA on LinkedIn