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.

The Role Zipline’s core product is the engine behind how the world’s best retailers operate their frontline, and it’s evolving fast. As we build toward an AI-first frontline operations platform, the Director of Product, Core products is the leader accountable for making that evolution real across everything we ship today. This role collaborates on the product strategy, team performance, and business outcomes for Zipline’s core platform: the tools used daily by 620,000+ frontline workers across 200+ world-class brands. You will lead a formed team of product managers, own the 12–18 month roadmap, and serve as the connective tissue between day-to-day execution and Zipline’s five active strategic pillars. This is a senior people leadership role for someone who has been here before. You will inherit a talented, formed team and be expected to run it: elevating craft, moving decision-making down, and creating the conditions for PMs to operate with autonomy and accountability, driving a roadmap that is creating revenue for the business, while bringing the team forward with AI-enabled workflows. You report to the SVP, Product and act as a peer to the Director of Product, Strategic Ventures. Together you represent the full span of Zipline’s product ambition: you execute on what exists and evolves today; your peer bets on what comes next. You are the strategic execution layer the SVP needs in order to operate at a company-level altitude.

What You’ll Do

Own the core product roadmap Define and maintain the 12–18 month product roadmap across Zipline’s core platform pillars. Translate Zipline’s vision and strategy into clear, sequenced, evidence-backed product investments. Ensure every PM on your team owns a strategy (not just a backlog) and can speak to outcomes, not features. Build rigorous roadmap narratives that give executives and stakeholders clarity on where we are going and why. Be capable of representing Zipline’s core product story compellingly on stage at Summer Camp, and other various customer and prospect-focused functions, as well as in customer conversations, and in cross-functional planning.

Lead and develop a high-performing PM team Manage, coach, and develop a team of product managers across Zipline’s core product pillars. Apply strong situational leadership, meeting each PM where they are, stretching those who are ready, supporting those who are developing, and holding the bar across the team. Drive the IC-to-leader transition on your team: build accountability, strategic thinking, and autonomous decision-making as norms. Hold a high bar on product craft: the quality of discovery, the rigor of prioritization, the clarity of outcome definition. Over time, identify and develop the next layer of leadership within your team.

Drive strategy-to-execution alignment across Engineering, Product, and Design (EPD) Own the translation of company strategy into product decisions, PM priorities, and quarterly plans. Serve as the escalation path for your PMs: unblock decisions, resolve cross-functional friction, and keep teams moving. Partner with Engineering and Design leadership to run a healthy, high-functioning EPD triad for the core business. Move decision-making down: structure your team so that day-to-day execution runs without requiring SVP involvement, and surface only what genuinely requires it. Flag risks, resource gaps, and strategic misalignment proactively. In partnership with Product Operations, lead the evolution of how the product team defines, prioritizes, and delivers work, building the operating muscle required to run an increasingly AI-augmented product organization.

Champion AI-first product thinking across the core platform Integrate AI strategy into the core product roadmap as a fundamental rethinking of what the platform can do, not a feature bolt-on. Work with your PMs to evolve Zipline’s AI capabilities across core operational, engagement, and intelligence use cases. Partner with Data Science and Engineering to validate feasibility, scope, and customer value of AI-enabled features. Help your team develop fluency with AI-native product thinking: what does an AI-first experience mean for this workflow, and what becomes possible for the customer? Ensure AI investments are grounded in retail domain knowledge and Zipline’s behavioral data moat, not generic capability shipping. Importantly (and in partnership with Product Operations) this means leading from the inside out, and supporting your product leaders in adopting AI into their own day-to-day craft and workflows, so that how we think, prioritize, and build reflects the same AI-first standard we hold for the product itself.

Represent the voice of the customer Build and maintain deep knowledge of Zipline’s customers, their frontline realities, and the problems that matter most to them. Use quantitative and qualitative signals to drive informed, defensible product decisions across your portfolio. Partner deeply with CS and Sales to ensure the roadmap reflects what is driving retention, expansion, and customer love today, and what will drive it tomorrow, keeping each imperative in a healthy balance. Bring customer perspective into executive discussions, strategic planning, and prioritization trade-offs. Understand retail store operations deeply enough to challenge assumptions, sharpen requirements, and advocate credibly for what frontline workers actually need.

What This Role Explicitly Does Not Own New vertical exploration, horizontal product extensions, or net-new growth bets (owned by Director of Product, Strategic Ventures) Long-term design strategy, design systems ownership, or design team management Engineering team management or technical architecture decisions Product-led growth mechanics or self-serve acquisition Corporate development, M&A assessment, or partnership support

Your mandate is to make what exists today exceptional as we achieve what’s next, and to evolve it with precision and speed as Zipline’s AI-first strategy comes to life. Strategic Ventures identifies what to bet on next. You make sure the core never stops getting better.

What Success Looks Like The Director, Product can operate at a company-level altitude: confident the next 12–18 months of core product execution are owned and running. Zipline’s core product team operates with clarity, ownership, and velocity: decision-making lives at the right level, not escalated upward by default. PMs on your team are growing: in craft, strategic thinking, and the ability to lead without being told what to do. The roadmap is coherent, sequenced, and evidence-backed: cross-functional partners and executives trust it and can act on it. Design and delivery of the Product Roadmap creates meaningful and direct revenue-impacting success to the business AI is woven into the core product roadmap as a genuine, differentiated capability — not a checkbox or a bolt-on. Customers feel the product getting better: faster, smarter, and more relevant to how their frontline actually operates. You can stand on stage and tell Zipline’s core product story as compellingly as anyone in the company. Core product teams receive validated opportunities from Strategic Ventures and can scale them confidently. The handoff is clean, not chaotic.

Compensation At Zipline, we're committed to paying our team fairly, transparently, and in a way that supports growth. This role is targeting an annual salary within Canada of $197,208 CAD to $241,008 CAD.

See the full compensation philosophy on the linked job posting.

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.

Learn about how we work in the full linked job description.

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