ATTENTION: WINNIPEG MARKETERS

Hey Winnipeg! We’re Looking for a Talented Business Development Rep to Join Our Team

Discover a workplace where your creativity is valued, your ideas matter, and your talent makes real impact. Join a growing team that values quality and attention to detail and gives you the space to do your best work.

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Are you a driven, detail-oriented Business Development Rep who thrives on turning conversations into real opportunities?

Then please read on…

We run a fast-growing consulting business called GetTruckDrivers.com that helps trucking companies solve driver shortages through strategic outreach, meaningful conversations, and booked meetings that turn into revenue.

In less than 3 years, we’ve scaled quickly and now work with some of the largest trucking companies in North America, all while maintaining strong results. Our system, outreach, and client growth rely heavily on precise research, sharp messaging, and disciplined execution to open doors at the highest levels.

Our mission is simple… help trucking businesses grow through better recruiting systems. Outbound outreach plays a critical role in how we start conversations, create pipeline, and turn opportunity into revenue across everything we build.

Due to our rapid growth, we’re looking for one Business Development Rep. This is where you come in—as the person who builds target lists, writes thoughtful cold outreach, books qualified meetings, and owns the number with consistency and discipline.

About the Role

This Role Aims To

Build And Own

Our Outbound Pipeline

Driving high-impact outreach that opens conversations with fleet decision makers, builds qualified target lists, and turns booked meetings into real revenue, all while maintaining the highest standards of research, precision, and execution.

We’ve grown fast because we think differently, and we are on the lookout for a Business Development Rep who does too.

You’ll join a tight-knit team where your outreach drives pipeline and shapes how our company opens doors at the highest levels.

CORE RESPONSIBILITIES

What you'll be Doing

Strategy & Growth

Build and own a targeted account list focused on fleet decision makers and executive leaders
Research companies deeply to craft highly specific, relevant cold outreach that earns replies
Open conversations that convert into qualified meetings and long-term revenue opportunities

Team Leadership

Work directly with leadership to refine outreach strategy and improve reply and booking rates
Participate in message reviews and feedback loops to sharpen clarity, positioning, and precision
Take full ownership of outreach execution and performance metrics, not just activity volume

Execution & Performance

Write and send personalized cold emails to CEOs, VPs of Recruiting, and Heads of Operations
Track responses, manage follow-ups, and consistently book qualified meetings
Analyze what works, iterate messaging, and improve performance through disciplined refinement

PERKS

Here is just the tip of the iceberg, you'll get at Get Truck Drivers

Discover a workplace where your talent is nurtured, and your career can flourish. Join a team that values growth, innovation, and your unique strengths.

Compensation & Growth

Base Pay + Commissions (Earning potential $100k year 1)

Annual Raise & Monthly Performance Reviews (PPF Scorecard)

Benefits & Wellbeing

Full Benefits After 6 Months (50% Paid by Us)

2 Weeks Paid Vacation + “5 - My Days” After 1 Year

Recognition & Support

Paid Conferences, Training & Courses

Book Reimbursement (Non-Fiction)

Apple Laptop Provided

Perks & Workplace Experience

Free Snacks & Health Drinks in the Office

Free Beer + Company Lunch Every Friday

Walking Treadmill & 24/7 Office Access

NON-NEGOTIABLE

Requirements

You are comfortable with cold outreach and understand that most emails will not get a reply.
You are confident writing clear, thoughtful cold emails to executives and decision makers.
You are highly disciplined with research and able to deeply understand a company before reaching out.
You take ownership of a target list and treat pipeline growth as your responsibility.
You are self-directed and able to execute consistently without needing daily instructions.
You can handle rejection, silence, and inconsistent weeks without losing focus or momentum.
You are honest enough to analyze what is not working and improve it instead of blaming the system.
You are serious about mastering persuasion, communication, and high-level outreach as a craft.

BONUS

Experience booking meetings with CEOs, VPs, or senior decision makers in B2B environments.
Background in cold email outreach, outbound prospecting, or account-based sales.
Experience generating pipeline or revenue directly from self-sourced outreach efforts.
Familiarity with performance-based compensation and a strong desire to earn on results.

testimonials

What others are saying

GetTruckDrivers is a place for ambitious individuals to grow personally and professionally. Here, you're not just another employee you're part of something meaningful.

"This has massively exceeded my expectations"

"The money here is real. There’s a lot to learn… but once you get over that hump and close your first unassisted sale, it hits you. It’s been game-changing seeing paychecks coming in from what was promised to me.”

- Courtney Greer

“If you want to be the author of your life… you need to be working here.”

"This company lets you leverage your work in a way that’s genuinely fulfilling. You can make the difference you want in your life and in the lives of others."

- Mark Stulzer

“It’s definitely an A-player culture.”

"You’re expected to work hard, generate results, and perform but you’re given all the tools to do it. And we still have a lot of fun… we’re a tight-knit team."

- John Vosper

“The success of the company is tied to your income.”

“We’re always trying to innovate. The better we get, the more value we provide… and the more money you make.”

- Justin Craddock

APPLICATION PROCESS

How to Apply:

Discover a workplace where your talent is nurtured, and your career can flourish. Join a team that values growth, innovation, and your unique strengths.

1. Submit an Application

Click the button below and fill out your application below with as much detail as to why you’d be a good fit. After submitting, it will take 24-48 hours to review your application.

2. Answer Video Questions

We’ll have a few questions for you to answer on Video about your experience and why you think you’ll be an excellent fit for the team.

3. Screening Interview

An interview with someone on our team to get to know a bit more about each other.

4. Skill Test Interview

We will set up a mock interview to test your communication and screening abilities.

5. Core Values Interview

We will conduct a final interview with the shortlisted candidates.

6. Hired

We will extend an official offer letter at this point to join our team. :)

OUR CULTURE

A Glimpse into our Culture

Discover a workplace where your talent is nurtured, and your career can flourish. Join a team that values growth, innovation, and your unique strengths.

Take the First Step Towards Your New Career

Join us and start building a rewarding career today—apply now! Your journey to professional fulfillment begins here.