Director of Product, Core Business

Highlightta Inc.

Job Overview

Location

Canada

Job Type

Full-time

Full Job Description

📋 Description

• Lead the 12–18 month product roadmap for Zipline’s core platform, used daily by 620,000+ frontline workers across 200+ global brands, ensuring every initiative is evidence-backed and tied to measurable business outcomes.
• Manage, coach, and develop a team of product managers, applying situational leadership to elevate craft, foster strategic thinking, and drive the IC-to-leader transition across the team.
• Own the translation of Zipline’s five strategic pillars into clear, sequenced product investments, ensuring alignment between company vision and day-to-day execution across Engineering, Product, and Design (EPD).
• Serve as the primary escalation path for PMs, unblocking cross-functional friction, resolving prioritization conflicts, and ensuring decision-making is delegated appropriately without unnecessary upward escalation.
• Integrate AI as a fundamental rethinking of core workflows—not as a bolt-on feature—by partnering with Data Science and Engineering to validate feasibility, scope, and customer value of AI-enabled capabilities across operational, engagement, and intelligence use cases.
• Champion AI-first product thinking across the team, ensuring PMs adopt AI-native approaches in their discovery, prioritization, and delivery processes, grounded in Zipline’s behavioral data moat and retail domain expertise.
• Build and maintain deep customer insight by leveraging quantitative and qualitative signals from frontline workers in retail, healthcare, and logistics, and translate those insights into defensible product decisions.
• Partner closely with Customer Success and Sales teams to ensure the roadmap reflects drivers of retention, expansion, and customer love, balancing immediate needs with long-term innovation.
• Represent Zipline’s core product story with authority in executive discussions, customer conversations, and public forums such as Summer Camp, ensuring clarity and compelling narrative around product direction.
• Drive evolution of product operating rhythms in partnership with Product Operations, building systems for defining, prioritizing, and delivering work that scales with an AI-augmented organization.
• Hold a high bar on product craft: ensure rigorous discovery, clear outcome definitions, and disciplined prioritization across all team initiatives.
• Identify and develop the next layer of product leadership within the team, creating a sustainable pipeline of strategic, autonomous product managers.
• Ensure the core product team operates with clarity, ownership, and velocity, where decision-making resides at the appropriate level and execution is autonomous from SVP-level involvement.
• Maintain strict boundary between core product ownership and strategic ventures: do not own new verticals, horizontal extensions, net-new growth bets, design systems, engineering management, technical architecture, or product-led growth mechanics.
• Deliver a roadmap that directly creates revenue impact, with measurable improvements in customer experience, operational efficiency, and frontline engagement.
• Ensure AI investments are differentiated and not generic, rooted in Zipline’s unique data and retail context, and demonstrably improve how frontline teams operate.
• Enable seamless handoff of validated opportunities from Strategic Ventures to the core product team, ensuring scalable execution without chaos or misalignment.

🎯 Requirements

• Proven experience leading a team of product managers in a SaaS environment with a complex, high-usage core product
• Demonstrated success in building and executing a 12–18 month product roadmap aligned to business outcomes and revenue impact
• Deep understanding of AI-first product development and ability to integrate AI as a foundational capability, not a feature
• Experience operating as a senior leader in a remote-first, globally distributed company
• Strong track record of elevating product craft, fostering strategic thinking, and enabling autonomy within product teams
• Proven ability to partner effectively with Engineering, Design, and Data Science leadership to run a high-functioning EPD triad

🏖️ Benefits

• Remote-first culture with flexibility to work from anywhere
• Stock options in a fast-growing, venture-backed company
• Flexible time-off policy with a monthly coffee-shop stipend and a fully paid one-month sabbatical after five years
• World-class medical, dental, and vision benefits
• Annual company off-sites in global locations
• Paid quarterly volunteering days and unlimited access to Udemy Business for continuous learning

Skills & Technologies

REST

Remote

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Highlightta Inc.

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About Highlightta Inc.

Highlightta provides AI-driven video clipping and automated highlight generation for sports, esports, and creator content. The platform ingests live or archived streams, detects key moments using computer vision and audio cues, and delivers ready-to-publish clips for social media. Customers include leagues, teams, broadcasters, and influencers seeking faster turnaround and higher engagement. Core features cover multi-stream support, customizable branding, real-time sharing APIs, and analytics dashboards that track clip performance across TikTok, Instagram, Twitter, and YouTube.

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