Director, Customer Success

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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.

About the Role

As Director, Customer Success, you’ll play a key role in shaping how Zipline delivers exceptional customer experiences while driving retention and growth. We’re looking for a seasoned Customer Success leader who combines strategic thinking with hands-on execution and thrives in a fast-paced, evolving environment.

Reporting to the VP, Customer Success, you’ll lead our Account Management function, owning customer retention, renewals, and expansion outcomes across a portfolio of enterprise customers, including some of the world’s most recognized retail brands. Zipline operates a high-touch customer success model, where building deep, trusted relationships and delivering measurable value are essential.

As we continue to grow globally, you’ll help evolve our team structure, processes, and ways of working to support scale. You’ll be a trusted partner to cross-functional leaders and play an important role in developing a high-performing team that consistently delivers exceptional customer outcomes.

What You’ll Do

Lead Account Management and Drive Customer Growth

• Lead and develop the Account Management team, fostering strong customer relationships and a culture of accountability and continuous improvement.

• Own retention, renewal, and expansion outcomes, ensuring customers realize ongoing value from Zipline.

• Maintain visibility into customer health, proactively addressing risks and identifying opportunities for growth.

Build and Scale Customer Success Operations

• Partner with the VP, Customer Success to evolve team structures, customer coverage models, and operational processes as the business grows.

• Lead organizational and operational changes that improve efficiency, team effectiveness, and the customer experience.

• Champion the adoption of AI, automation, and emerging technologies to streamline workflows, improve team capacity, and enhance customer outcomes.

Drive Cross-Functional Collaboration

• Partner closely with Sales, Product, RevOps, and other teams to represent customer needs and align business priorities.

• Act as a trusted decision-maker, navigating complex challenges and driving solutions with autonomy and sound judgment.

• Support the evolution of our global Customer Success operations, ensuring customers receive consistent, high-quality service across regions.

Develop and Inspire Your Team

• Coach and develop Account Management leaders and team members, building a culture of ownership, collaboration, and high performance.

• Identify opportunities for professional growth, succession planning, and continuous team development.

• Lead confidently through change, keeping teams engaged, aligned, and focused on delivering results.

What We Look For

Must-Haves

• Significant leadership experience in enterprise SaaS Customer Success or Account Management, including experience managing managers.

• Proven success driving customer retention, renewals, and expansion revenue within a high-touch enterprise customer model.

• Experience leading and scaling global or multi-region teams, including navigating organizational change and evolving customer coverage models.

• Strong commercial acumen, with the ability to balance customer relationships, business priorities, and revenue outcomes.

• Demonstrated ability to develop high-performing teams, influence cross-functional stakeholders, and make decisions independently.

• Experience operating in a scaling SaaS organization, ideally within the $30M to $100M ARR range.

• Comfort collaborating across global time zones, particularly with teams and customers in North America and Europe.

Nice-to-Haves

• Experience working alongside customer support or technical support functions.

• Background in retail technology or familiarity with retail store operations.

• Familiarity with Customer Success and CRM platforms such as Gainsight, Catalyst, or Salesforce.

• Experience leveraging AI or automation to improve Customer Success operations.

What Success Looks Like

You’ll build a high-performing Account Management function that consistently delivers strong customer retention, meaningful expansion revenue, and exceptional customer satisfaction. Your team will operate with clarity and accountability, customer relationships will deepen, and you’ll be recognized as a trusted leader who can navigate complexity, drive change, and help Zipline scale successfully.

This role may require up to 25% travel.

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 $184,714 CAD to $225,762 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 $184,714 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 conversat…