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HighlightTA
Development 4h ago

Director of Product, Core Business at Zipline

HighlightTA
CanadaCanada
Full-time
$230,000 CAD to $290,000 CAD
Senior-Level

Job Description

Key Skills Required

Master these to land this role

Roadmap StrategyAI & Machine LearningEnterprise B2B SaaSProduct ManagementCross-functional Leadership

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Zipline is a well-funded, rapidly growing SaaS company transforming how frontline teams work. They empower leading brands across retail, healthcare, logistics, and beyond to connect, align, and inspire their employees—from headquarters to the front lines. Zipline is a fully remote company with employees across the U.S., Canada, and globally.

The Role

Zipline's core product powers frontline operations and is evolving into an AI-first platform. As Director of Product, Core Business, you will:

  • Lead the strategy, roadmap, and execution for Zipline's core platform, serving 620,000+ frontline workers across 200+ global brands.
  • Lead an established team of Product Managers and shape the 12 to 18-month roadmap.
  • Ensure product investments drive customer value, business growth, and platform innovation.
  • Report to the SVP of Product and translate company strategy into product outcomes.
  • Build a high-performing product organization tailored to an Enterprise B2B SaaS company.
  • Partner closely with Engineering, Design, Customer Success, Sales, and other cross-functional leaders.
  • Embed AI-first thinking across the 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 driving customer and business outcomes.
  • Balance customer needs, market opportunities, and technical considerations for 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 for consistently high-quality outcomes.

Drive Cross-Functional Execution

  • Partner closely with Engineering and Design leadership to deliver strategic priorities.
  • Align teams around shared goals, resolve obstacles, and ensure effective planning and execution.
  • Continuously improve product team operations and scalability.

Champion AI-First Product Innovation

  • Integrate AI capabilities into the core product strategy for meaningful customer value.
  • Adopt AI-native ways of thinking and working across the product organization.

Represent the Customer

  • Develop a deep understanding of customer needs, frontline operations, and market trends.
  • Partner with Customer Success and Sales to align roadmap priorities with 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.
  • Engineering management or technical architecture.
  • Design organization leadership.
  • Product-led growth strategy.
  • Corporate development or partnerships.

What Success Looks Like

  • A clear, strategic roadmap delivering 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 product organization.
  • Continued growth in customer satisfaction, adoption, and revenue driven by the core platform.
  • A trusted product leader who confidently represents Zipline's product vision internally and externally.

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HighlightTA is a highly agile, on-demand Talent Acquisition (TA) partner fundamentally designed to replace the traditional, expensive recruitment agency model for high-growth startups and scale-ups. Operating with a strong remote footprint across North America, the company functions not as a passive vendor, but as an embedded internal talent team. Under the hood, HighlightTA deploys a suite of highly tailored hiring solutions—IntegrateTA for plugging dedicated recruiters directly into a company's Slack and internal workflows, FunctionTA for architecting and managing the entire end-to-end recruitment lifecycle, and ProjectTA for rapid, high-impact hiring sprints. Their primary target audience spans aggressive tech scale-ups (including prominent clients like Q4 Inc., Zipline, and Certn) that desperately need to rapidly scale their engineering, sales, and account management teams while completely dodging bloated traditional agency fees. What sets HighlightTA apart in the fiercely competitive HR ecosystem is its proprietary Data-Driven Recruitment (DDR) model and "plug-in, plug-out" flexibility; they actively engineer global talent strategies, optimize employer branding, and execute with absolute precision to deliver enterprise-grade hiring at a fraction of the cost.

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Director of Product, Core Business at Zipline at HighlightTA | HireSkys