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Director, Implementation & Services

Job in Toronto, Ontario, M5A, Canada
Listing for: HighlightTA
Full Time position
Listed on 2026-03-01
Job specializations:
  • IT/Tech
    IT Project Manager, IT Consultant
  • Management
    IT Project Manager
Salary/Wage Range or Industry Benchmark: 147966 CAD Yearly CAD 147966.00 YEAR
Job Description & How to Apply Below
Highlight

TA 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.

Our Implementation & Services team is at the heart of that mission, guiding new customers through onboarding, deployment, and adoption while ensuring every rollout is seamless, strategic, and impactful.

About the Role
The Director, Implementation & Services  leads the teams responsible for both customer onboarding and technical account management. This is a senior leadership role that sets the strategic direction for how Zipline brings new customers live, scales its implementation capabilities, and leverages emerging AI and agentic technologies to drive efficiency across the customer journey. You'll ensure that every new customer experiences a world-class Zipline launch — from initial planning and configuration to post-launch optimization — and that the systems and processes supporting them are built to scale.

You’ll lead a team of Implementation Managers, Implementation Engineers, and Technical Account Managers who work directly with customers to design workflows, configure systems, map business requirements, manage integrations, and deliver outstanding results. As a Director, you’ll also be a key voice in shaping organizational strategy, influencing cross-functional priorities, and building a high-performing team culture.

Key Responsibilities
Team Leadership & Development

Lead, mentor, and develop a growing team of Implementation Managers,

Implementation Engineers, Technical Account Managers, and Team Leads.

Establish clear goals, processes, and best practices to drive excellence across

onboarding and technical service delivery.

Define and own the strategic vision for the Implementation & Services function,

including multi-year roadmaps for process maturity and team growth.

Foster a collaborative, customer-obsessed culture focused on proactive communication, accountability, and continuous improvement.

Partner with senior and executive leadership to forecast team capacity, manage resources, and plan for scale.

Explore and develop revenue-generating opportunities within the Implementation & Services department, including managed services, accelerated onboarding packages, and premium technical advisory offerings.

AI Driven Transformation & Automation

Champion the adoption of AI and agentic workflows across the implementation lifecycle — identifying high-impact opportunities to reduce manual effort, accelerate time-to-value, and improve consistency at scale.

Design and oversee intelligent automation initiatives that streamline onboarding tasks such as configuration, data mapping, integration setup, and customer communication.

Draw on prior experience deploying AI-assisted or agentic tooling in implementation or professional services environments to lead Zipline's transformation with confidence and credibility.

Partner with Product and Engineering to evaluate and integrate AI-powered tools into implementation workflows, from project management automation to intelligent customer-facing guidance.

Establish metrics and feedback loops to measure the impact of AI initiatives on implementation speed, team capacity, and customer experience.

Stay current on emerging AI and automation technologies relevant to SaaS implementation and retail operations, and translate that knowledge into actionable strategy for the team.

Implementation Management

Oversee all new customer onboarding projects, ensuring successful and timely Zipline launches.

Guide the team in coordinating project tasks, managing timelines, and maintaining clear communication with customers and internal stakeholders.

Ensure project scope and requirements are…
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