Strategic Sales Director

Zipline is the unified platform that connects every level of a retail business – from strategic vision to day‑to‑day store execution. Our platform is pressure‑tested in retail, one of the most complex and distributed industries. It brings teams together across hundreds of locations and thousands of employees, improving customer satisfaction, sealing communication gaps and boosting operational efficiency. Built by retail, for retail. Zipline was born out of our co‑founder’s frustration with outdated tools and communication challenges in store operations. Today, leading retailers like Sephora, American Eagle and Rite Aid use Zipline to align their fleet, empower their frontline and execute with precision.

As we continue to scale across North America, we’re seeking a Strategic Sales Director to join our new business team. This role is ideal for a high‑performing enterprise seller passionate about transforming operations at large retail organizations through technology.

You will lead the full sales cycle and partner cross‑functionally to win complex, multi‑stakeholder deals with Fortune 1000 retailers.

• Own the full sales cycle—from account targeting, pipeline generation and outreach through discovery, value modelling, negotiation and contract close.
  
• Build and nurture senior relationships with C‑suite and VP‑level decision‑makers across retail operations, store communications, IT, HR and finance.
  
• Develop tailored GTM plans for high‑priority accounts in partnership with marketing, solutions consulting and SDR teams; orchestrate internal resources to deliver demos, business cases and proofs of concept.
  
• Navigate complex procurement, legal and security review processes to close six‑ to seven‑figure net‑new logos.
  
• Maintain an accurate pipeline and forecast in Salesforce/Clari, providing clear updates and strategic insights to leadership.
  
• Serve as the voice of the customer, communicating market trends and feedback to product and marketing teams.
  
• Represent Zipline at industry events, trade shows and networking forums.
  

• 10+ years of enterprise SaaS sales experience with a consistent record of closing large, multi‑stakeholder deals (ideally six‑ to seven‑figure) in the retail or consumer‑facing sectors.
  
• Proven success selling into Fortune 1000 retailers and navigating matrixed organizations across operations, IT and HR.
  
• Deep understanding of retail operations and communications; ability to credibly discuss frontline execution and the ROI of unifying teams.
  
• Mastery of structured sales methodologies (e.g., MEDDICC, Command of the Message, Challenger, Value Selling) and experience building executive‑level business cases.
  
• Exceptional communication skills and executive presence; comfortable delivering board‑level presentations.
  
• Self‑starter who thrives in a high‑growth, remote‑first environment; adept at collaborating across marketing, product and customer success.
  
• Passion for retail and appreciation for the challenges of frontline enablement.

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!

If you’re a strategic seller who thrives on winning complex deals and building relationships with world‑class brands, we’d love to meet you.