Sales Representative

DataDocks • Toronto, ON

8d • Remote

About The Position

At DataDocks, we keep things simple. If something makes sense, we try it. If it works, we ship it. If it doesn’t, we fix it. No layers. No waiting around for approvals. People talk to customers directly. Product feedback turns into real changes quickly. And everyone here actually owns what they’re working on. It’s a small team — which means your impact is visible, your work matters, and you’re never stuck feeling like you’re “one step removed” from the outcome. That’s the kind of environment we’ve built. We build software for warehouse teams still managing dock scheduling with spreadsheets, whiteboards, phone calls, and a lot of manual coordination. It works — but it’s clunky, slow, and harder than it needs to be. So we built something better. Simple, fast software that actually fits how real logistics operations run day to day. It’s already being used by logistics teams across North America. We’ve grown without outside funding and without adding unnecessary complexity along the way. Now we’re looking for someone to help us bring it to more teams. We’re looking for a sales professional who enjoys the full process. Someone who likes talking to customers. Someone who can understand real-world problems quickly. Someone who can take a deal from first conversation all the way to close. No heavy scripting. No rigid playbook. Just good fundamentals, good judgment, and the ability to build trust with operators.

Requirements

• 5–10 years in B2B sales (SaaS or logistics is a strong asset)
• Proven track record of closing deals and owning a pipeline
• Strong communicator who can simplify complex ideas
• Competitive but collaborative, not cutthroat
• Genuinely cares about customers
• Comfortable taking ownership in a fast-moving environment

Nice To Haves

• Have sold technical or operational software before
• Enjoy figuring things out without a 40-page playbook
• Naturally look for ways to improve systems and processes

Responsibilities

• Hunt & Close Deals
• Build your own pipeline (outbound, inbound, referrals)
• Run discovery calls that feel like real conversations, not interrogations
• Deliver demos that make people pause and say: “wait… we need this”
• Become a Logistics Whisperer
• Learn how warehouses actually run (and why it’s often chaotic)
• Turn real operational pain into clear “aha” moments
• Build credibility with operators by speaking their language
• Keep Things Moving (Without Being Annoying)
• Follow up like a human, not a CRM sequence
• Manage deals through a 30–90 day cycle without losing momentum
• Know when to push, when to pause, and when to close
• Shape What We Build
• Work directly with the founder and product team
• Share what you’re hearing in the field (good, bad, and everything in between)
• Help shape how we sell—and occasionally what we sell

Benefits

• Remote-first (Canada)
• Full benefits – health, dental, all the basics
• Base salary + uncapped commission — meaningful upside on every deal
• High trust, low micromanagement environment
• Your ideas actually shape the product and how we grow
• Annual team retreat

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed