Director, Implementation & Services

HighlightTA 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 clearly defined, tracked, and delivered within expectations.

Support the team in leading clients through workflow design, configuration, and rollout — ensuring solutions align with best practices.

Maintain high customer satisfaction through responsiveness, thorough communication, and ongoing engagement.

Technical Account Management

Oversee technical design and implementation of customer solutions, including integrations, data feeds, and platform configurations.

Partner cross-functionally with Product, Engineering, and Account Management to align customer needs with product capabilities.

Guide the team in providing proactive technical support, resolving issues, and identifying opportunities for optimization.

Ensure TAMs build strong, consultative relationships with customer stakeholders, serving as trusted technical advisors.

Review and evolve processes for managing upgrades, third-party integrations, and custom configurations.

Cross-Functional Collaboration

Collaborate with Sales and Solutions Engineering on scoping and pre-sales planning for complex retail deployments.

Work closely with Customer Success to ensure smooth transitions from implementation to steady-state account management.

Partner with Product and Engineering to communicate customer feedback and influence product roadmap priorities.

Partner with the Support organization to ensure implementations and projects are properly documented and handed off, setting the support team up to be the primary ongoing point of contact.

Represent Implementation & Services at the leadership level, contributing to company-wide strategy and cross-departmental planning.

Must Haves

8+ years of experience in software implementation, professional services, or technical account management, preferably in a SaaS environment and ideally with retail as a vertical.

4+ years of experience managing and developing teams in customer onboarding, implementation, or technical services, including experience leading team leads or managers.

Demonstrated experience adopting and operationalizing AI tools, agentic workflows, or intelligent automation within an implementation or professional services context — either by leading initiatives at a prior organization or by driving meaningful transformation within a team.

Preferably, experience in retail, working with retail customers or in a headquarters environment.

Demonstrated ability to communicate, present, and influence credibly and effectively at all levels of the organization, including executive stakeholders.

Experience delivering client-focused solutions based on customer needs.

Ability to manage multiple strategic initiatives simultaneously while maintaining attention to detail and team accountability.

Experience with project management software such as Basecamp, Asana, Jira, etc.

Experience with knowledge management software such as Confluence

Technical experience delivering integrations such as Single Sign On, SFTP data feeds, and working with APIs.

Proven experience configuring and managing Jira and Confluence for implementation projects, including workflow design, dashboard creation, and system optimization.

Has led the creation and review of Statements of Work (SOWs) to support strategic initiatives, ensuring alignment with organizational goals, legal standards, and vendor capabilities.

Proven problem-solving skills and a proactive approach to addressing challenges before they escalat

Enjoys fostering a positive, collaborative environment and believes work can be both productive and fun.

Self-starter with strong organizational, presentation, interpersonal, and consultative skills

Outstanding listening and writing skills, with a keen ability to translate complex concepts into clear, intuitive communication.

Team player with excellent collaboration skills to build relationships across the company and with customers.

Highly organized with a strong track record managing relationships and supporting onboarding efforts at scale.

PMP certification or equivalent experience.

Familiarity with CRM platforms like Salesforce and Catalyst, and project management tools like Jira.

Familiarity with third-party systems such as Workforce Management, Learning

Management, Customer Experience, and Work Orders.

Compensation At Zipline, we’re committed to paying our team fairly, transparently, and in a way that supports growth. This role has a minimum annual salary within Canada of $147,966 CAD and a maximum of $221,950 CAD. This role has a minimum annual salary in the USA of $167,260 and a maximum of $250,890 USD.

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 USA band means a starting salary of $188,178

USD Within the Canadian band, $166,462 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, produ...