Strategic Sales Director

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 Zipline continues to expand globally, we’re looking for a Strategic Sales Director to help grow our presence across Australia and the broader APAC region. This is an opportunity for an experienced enterprise seller who combines strategic sales expertise with the versatility and entrepreneurial mindset needed to build in an emerging market and build on the success we have built with Super Retail Group, Cotton-On, Princess Polly and others. The foundation is there for the right commercial owner to drive the region forward in its next stage of growth.

You’ll own the full sales cycle for complex enterprise opportunities, building relationships with senior leaders at some of the region’s largest retailers and consumer-facing organizations. As an early sales leader in the region, you’ll need to be comfortable wearing multiple hats: generating pipeline, developing account strategy, leading executive conversations, coordinating internal resources, navigating complex deals, and helping shape how Zipline goes to market in APAC.

This role is ideal for someone who knows how to operate independently without operating in isolation. You’ll have the support of Zipline’s global Sales, Solutions Consulting, Marketing, Product, and Customer teams, while bringing the judgment and initiative to move opportunities forward without waiting for a fully established regional playbook.

What You’ll Do

Own and grow the APAC enterprise pipeline

• Own the full sales cycle from account targeting and pipeline generation through discovery, value modelling, negotiation, and close. Develop thoughtful strategies for high-priority accounts and build relationships with C-suite and VP-level leaders across retail operations, communications, IT, HR, Finance, and other key functions.

Win complex enterprise deals

• Lead sophisticated, multi-stakeholder sales processes with large enterprise organizations. Build compelling business cases, navigate procurement, legal and security reviews, and orchestrate the right internal resources to close significant six- and seven-figure opportunities.

Build the market, not just the pipeline

• Help establish and refine Zipline’s go-to-market approach in Australia and APAC. Bring a builder mindset to the role, identifying what works in the region, creating repeatable approaches, developing relationships and networks, and sharing insights that strengthen our broader regional strategy.

• You won’t always have a large local team or established process to lean on, so you should be equally comfortable setting strategy and rolling up your sleeves to execute it.

Partner across the business

• Work closely with Solutions Consulting, Marketing, SDRs, Product, Customer Success, and Sales leadership to move opportunities forward. Coordinate demos, business cases, proofs of concept, executive engagements, and other resources based on what each deal requires.

• Serve as a voice of the APAC market internally, sharing customer feedback, competitive intelligence, and emerging trends with Product, Marketing, and leadership.

Operate with rigor and autonomy

• Maintain an accurate pipeline and forecast in Salesforce and Clari, providing leadership with clear visibility into deal progress, risks, and opportunities. Use structured sales methodologies to qualify effectively, prioritize your time, and move complex opportunities forward.

• Represent Zipline at industry events, customer meetings, trade shows, and networking opportunities across the region.

What We Look For

Must Haves

• 10+ years of enterprise SaaS sales experience with a consistent track record of closing complex, multi-stakeholder deals, ideally in the six- to seven-figure TCV range

• Experience selling into large enterprise organizations, ideally major retailers or other complex consumer-facing businesses

• Proven ability to build a territory or market where the sales motion, local infrastructure, or brand presence is still developing

• A broad commercial skill set: you’re equally comfortable prospecting, building account strategy, running discovery, developing an executive business case, negotiating, and closing

• Strong executive presence and the ability to build credibility with C-suite and VP-level stakeholders

• Deep understanding of complex enterprise buying processes and experience navigating procurement, legal, IT, security, and other stakeholders

• Experience with structured sales methodologies such as MEDDICC, Command of the Message, Challenger, or Value Selling

• Strong business judgment and the autonomy to make progress without requiring a detailed playbook or constant direction

• A highly collaborative approach and experience partnering with Solutions Consulting, Marketing, Product, and Customer Success

• Comfort operating across global teams and time zones in a remote-first environment

• Willingness to travel across Australia and APAC as customer and business needs require

Nice to Haves

• Experience selling technology into retail organizations

• Strong understanding of retail operations, frontline communications, or workforce technology

• Existing relationships or networks within the Australian or broader APAC retail market and associated industry partners

• Experience joining a company early in its expansion into a new geography and helping establish the regional GTM motion

What Success Looks Like

You establish Zipline as a credible enterprise partner in the Australian and broader APAC market while building a healthy, high-quality pipeline of strategic opportunities.

You develop trusted executive relationships with major retailers, navigate complex sales cycles effectively, and consistently move the right opportunities toward close. Just as importantly, you help Zipline learn the market: bringing back insights, sharpening our regional approach, and creating repeatable practices that make it easier for the broader team to scale behind you.

Over time, your impact is visible not only in the revenue you close, but in the foundation you help build for Zipline’s continued growth across APAC.

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 base salary within Australia of $212,066.10 AUD to $259,191.90 AUD. 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 Australian band is $212,066.10 AUD. 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 5-10% multipliers on our ranges, depending on the location, to maintain competitive compensation and reflective of 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.


What's In It For You

• 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.

Want to learn more about how we work?

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.

We can't wait to meet you!

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