[Hiring] Director of Product @HighlightTA

Role Description

Zipline's core product powers how leading retailers operate their frontline, and we're evolving it into an AI-first platform for frontline operations. As Director of Product, Core Business, you'll lead the strategy, roadmap, and execution for Zipline's core platform, serving more than 620,000 frontline workers across 200+ global brands. You'll lead an established team of Product Managers, shape the 12 to 18 month roadmap, and ensure our product investments drive customer value, business growth, and platform innovation.

Reporting to the SVP of Product, you'll be responsible for translating company strategy into product outcomes while building a high-performing product organization that meets the unique and complex needs of an Enterprise B2B SaaS company. You'll partner closely with Engineering, Design, Customer Success, Sales, and other cross-functional leaders to deliver meaningful business impact and embed AI-first thinking across our platform.

What You'll Do

• Lead Product Strategy and Execution
  • REQUIRED experience leading Product for an Enterprise B2B SaaS product (non-negotiable).
  • Own the vision, roadmap, and prioritization for Zipline's core platform.
  • Translate company strategy into clear product investments that drive customer and business outcomes.
  • Balance customer needs, market opportunities, and technical considerations to make informed product decisions.
• Develop a High-Performing Product Management Team
  • Lead, coach, and grow a team of Product Managers.
  • Foster strong product thinking, accountability, and autonomous decision making.
  • Build an environment where teams consistently deliver high-quality outcomes.
• Drive Cross-Functional Execution
  • Partner closely with Engineering and Design leadership to deliver against strategic priorities.
  • Align teams around shared goals, resolve obstacles, and ensure effective planning and execution.
  • Continuously improve how product teams operate and scale.
• Champion AI-first Product Innovation
  • Integrate AI capabilities into the core product strategy in ways that create meaningful customer value.
  • Help both the product and product organization adopt AI-native ways of thinking and working.
• Represent the Customer
  • Develop deep understanding of customer needs, frontline operations, and market trends.
  • Partner with Customer Success and Sales to ensure roadmap priorities support retention, expansion, and long-term growth.
  • Represent the core product vision with customers, prospects, and at company events.

What This Role Does Not Own

• New product incubation or future growth ventures (owned by the Director of Product, Strategic Ventures)
• Engineering management or technical architecture
• Design organization leadership
• Product-led growth strategy
• Corporate development or partnerships

What Success Looks Like

• A clear, strategic roadmap that delivers measurable customer and business impact.
• A high-performing Product Management team with strong ownership and execution.
• Cross-functional teams operating with clarity, speed, and alignment.
• AI meaningfully embedded into both the product and the way the product organization works.
• Continued growth in customer satisfaction, adoption, and revenue driven by the core platform.
• A trusted product leader who can confidently represent Zipline's product vision internally and externally.

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 $230,000 CAD to $290,000 CAD. The broad salary ranges reflect the growth someone will experience in the role—from developing skills to reaching 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 on the Canadian band is $230,000 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 and paying competitively. 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: 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. After five years, you'll earn a fully paid one-month sabbatical.
• Benefits: World-class medical, dental, and vision policies.
• Team Connection: Annual company off-sites in fun locations.
• 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.

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.