Sales Representative

DataDocks; Toronto; Remote; CAD 70,000 - 110,000; Full time

Job summary

A fast-growing team at DataDocks is seeking a mid-senior level salesperson who thrives on closing deals and understanding customer needs in the logistics sector. As part of a small but impactful team, you will own the sales process from prospecting to closing, with full support and autonomy to shape outcomes.

Benefits

Full benefits – health, dental, all basics covered

No cap on commission

Annual retreat

High ownership, zero micromanagement

Qualifications

• 5–10 years of proven B2B sales experience, ideally in SaaS or operations/logistics tech.
• Sharp, articulate, and naturally good with people.

Responsibilities

• Own the full sales cycle, from first touch to signed contract.
• Find opportunities, run discovery, deliver demos, and close deals.
• Tailor each pitch for customer needs.

Skills

B2B Sales

Closing Deals

Customer Management

Autonomy

Communication

Job description

3 days ago Be among the first 25 applicants

We're not looking for someone to manage a spreadsheet. We're looking for a closer.

If you're the type of salesperson who gets a rush from chasing down real problems, running your own pipeline, and closing deals that actually matter, you'll feel at home here.

At DataDocks, we help warehouse and logistics teams take control of their docks. No more chaos. No more paper shuffles. Just simple software that brings order to the floor. We're used by some of the biggest names in retail and distribution across North America and now it's time to scale that momentum.

You'll own deals from day one, have a direct line to the founder, and help shape what sales looks like as we grow. This is a role for a doer, not a manager-in-waiting. That may come later, but right now, it's about results.

About Us

We started in a spare bedroom. No funding, no fluff, just customer obsession, product-market fit, and lots of shipping.

Now we're a remote-first, bootstrapped team building real tools for real people. We care deeply about the work and the people doing it.

What We Believe

• Teams and people come first
• Help the customer win (it's a core value, not just a slogan)
• Keep it simple, always
• Work without red tape, own it and run with it
• Take pride in what you do, and work with others who do too
  
  

We're small, scrappy, and serious about building a business we're proud of, without burning out in the process.

What You'll Be Doing

You'll own the full sales cycle, from first touch to signed contract. You'll get support, but the win is yours to chase.

Prospect, Pitch, Close

• Find opportunities (outbound, referrals, inbound, whatever works)
• Run discovery, deliver demos, close deals
  
  

Understand the Customer

• Learn how warehouse teams work and speak their language
• Connect our product to real pains and outcomes
  
  

Craft Proposals That Land

• Tailor each pitch, we don't do cookie-cutter decks
  
  

Follow Up Like a Pro

• Keep deals moving without becoming a pest
  
  

Own Your Number

• Hit your targets and get rewarded for it
• Typical sales cycles: 30–90 days
  
  

Work With the Team

• Tight feedback loop with product and CS
• Direct access to the founder
  
  

Help Shape What Comes Next

• Influence the sales playbook
• Option to grow into a team leadership role
• Your input will help shape the product
  
  

Why You'll Love It Here

• Remote from anywhere in Canada
• Full benefits – health, dental, all the basics covered
• No cap on commission – if you close more, you earn more, deal sizes run from low 5 figures to 6 figures
• High ownership, zero micromanagement
• Real impact – small team, big stage
• Annual retreat – we meet up once a year, somewhere nice
• Growth runway – leadership optional, but available
• Tools that work – CRM, outreach tools, lead lists, marketing support
  
  

What We're Looking For

• 5–10 years of proven B2B sales experience, ideally in SaaS or operations/logistics tech
• You're a closer, not just a “relationship builder”
• You thrive with autonomy and hit your numbers without hand-holding
• You're sharp, articulate, and naturally good with people
• You care about your customers' success as much as your commission
• You want to grow, not just in title, but in skill and scope
  
  

Why You Shouldn't Work Here

We're not for everyone and that's intentional.

• If you need a big support team to get things done, this isn't the place. The whole team will help support you, but we are lean! We expect you to take the wheel.
• If you're looking for a polished machine with layers of process, we're not there yet and that's part of the fun.
• If you need constant direction or reminders, you'll feel lost here. We're big on autonomy, and we expect you to own your outcomes.
• If you're just in it for a title, this isn't a stepping-stone job. You'll grow if you earn it, not because of your resume.
  
  

We're building something real, with real customers, and real expectations. It's not easy, but it's worth it.

Nice-to-Haves (but Not Deal Breakers)

• AE experience in a fast-growing SaaS company
• Background in logistics, transportation, or warehouse tech
• Been in founder-led sales and want to help scale it up

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Transportation, Logistics, Supply Chain and Storage

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