Strategic Sales Director
Zipline
- Canada
- Permanent
- Full-time
- 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.
- 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.