Director, Customer Success
HighlightTA
Director, Customer Success
HighlightTA
On-demand talent recruitment and function outsourcing
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.
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.
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.
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.
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.
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.
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.
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.
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.
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 the United States of $177,678- $217,162 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 is $177,678 USD. 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 conversations with your manager to ensure your compensation grows as you advance.
Our salary ranges are determined by market, factoring in our revenue and employee size and paying competitively. In higher cost of living markets, we apply 5 to 10% multipliers on our ranges, depending on the location, to maintain competitive compensation and reflect the increased expenses our team members face in those areas. While we primarily hire in Canada and the USA, we are a global employer, and all hiring regions will use the same methodology to determine fair and transparent pay.
Transparency is key to building trust in our compensation process. To better understand how this range is determined, we encourage you to ask as many questions as you’d like about compensation during the interview process to ensure clarity and confidence.
Remote-first culture: Join a high performing, fully remote team and work where you’re comfortable.
Stock Options: Get meaningful ownership in a fast-growing, venture-backed company shaping the future of retail.
Time off: We believe rest fuels great work. Our flexible time-off policy gives you the freedom to take the breaks you need, when you need them, whether it’s a long weekend or a well-deserved vacation. We’ll also give you a monthly coffee-shop stipend to switch up your workspace and get inspired outside the office. And when you’ve been with us for five years? You’ll earn a fully paid one-month sabbatical to truly unplug and reflect. We call it a thank-you for your impact and dedication.
Benefits: World-class medical, dental, and vision policies.
Team Connection: Annual company off-sites in fun locations. We’ve done New York, Costa Rica, Whistler, Palm Springs, San Diego, and Mexico City.
Volunteering: Every quarter, Zipliners get a paid day off to volunteer for a nonprofit of their choice.
Learning: We support continuous learning and provide unlimited access to our Udemy Business account.
Great humans, great work: Work with kind, collaborative teammates who care about doing meaningful work and making a real impact. We value diversity of all kinds and are committed to building a diverse and inclusive workplace where we learn from each other. We are an equal opportunity employer and welcome people of all different backgrounds, experiences, abilities, and perspectives.
We may be remote, but we’re anything but disconnected. Zipline is a thriving, dynamic team spread across the globe, collaborating, innovating, and having a blast along the way.
Zipliners work from all over: vans, boats, Airbnbs, and everything in between. No office? No problem. Our culture still feels like one big hug.
Even though we’re distributed, we make space to connect, whether it’s our weekly all-company social or gathering in person at our yearly retreats. We’re building something meaningful together, and we’re glad you’re considering being a part of it.
How We Hire
We use AI tools to support our recruitment process, including helping us organize applications and identify early matches based on role criteria. That said, every rejection decision is made by a human. We encourage candidates to apply authentically and avoid relying solely on AI-generated responses, especially during interviews.
This opportunity is offered through HighlightTA, the on-demand talent team supporting Zipline’s growth.
Connect with us and learn more:
Zipline on Linkedin
HighlightTA on LinkedIn
On-demand talent recruitment and function outsourcing
HighlightTA embeds talent partners into client teams to streamline hiring. It can lead recruitment projects or manage an entire talent function on an on-demand basis, allowing clients to scale hiring efforts up or down without long-term commitments or high agency fees. The offering uses a data-driven approach to quickly access top talent, saving time and reducing recruitment costs. Its services include integrating talent partners, overseeing recruitment functions, and delivering one-off projects through ProjectTA, all tailored to the client’s needs. The goal is to help clients build exceptional teams efficiently and cost-effectively while maintaining flexibility.
Explore more opportunities at HighlightTA