About Mortgage Automator Founded in 2017 and headquartered in Toronto, Mortgage Automator is the leading all-in-one SaaS platform purpose-built for private and asset-based lenders. Powering over $95+ billion in funded loans across 400+ lenders, our SOC 2 Type II-certified software streamlines the entire lending lifecycle—from origination and servicing to investor management—enabling clients to reduce risk and operate with unmatched speed and compliance. Fueled by a strategic 2024 investment by

BVP Forge , we are entering a dynamic phase of accelerated growth and product expansion, making this the perfect time to join us in redefining the non-bank lending landscape.

We are seeking a high-caliber, hunter-mentality

Account Executive

to join the Mortgage Automator team. This is not a role for "order takers." We are looking for sophisticated sales professionals who thrive on owning the

full opportunity cycle —from the first cold touch to the final signature on a multi-year agreement.

The ideal candidate is an expert at

value-based selling , using active listening to transform complex prospect pain into a strategic path toward a decision. You should be as comfortable building an outbound prospecting engine as you are navigating high-stakes negotiations with C-suite stakeholders.

The Role You will be responsible for targeting mid-market private lending organizations across North America, selling a mission-critical Loan Origination and Servicing platform. Your goal is to modernize their operations by demonstrating clear ROI and driving a sense of urgency in a competitive landscape.

Key Responsibilities

Full Cycle Ownership:

Be the CEO of your territory. You will own everything from targeted outbound prospecting to discovery, demo, and closing.

Strategic Outbounding:

Drive your own pipeline by researching and engaging a list of targeted accounts.



You are expected to leverage modern

AI tools (like Claude)

to automate research and scale your outreach without losing personalization.

Value-Based Discovery:

Move beyond features. Use

exceptional active listening

to uncover deep business impacts and build a clear, structured path to a decision for your prospects.

Complex Deal Navigation:

Manage multi-stakeholder environments, aligning the needs of IT, Operations, and Finance to secure buy-in.

Contract Negotiation:

Confidently negotiate diverse pricing models and packaging to secure

multi-year agreements

that benefit both the client and the company.

Urgency & Momentum:

Master the art of the "close" by creating genuine urgency and maintaining momentum through long-term sales cycles.

Proven SaaS Closer:

You bring

2-4 years of software sales experience , with a track record of consistently meeting or exceeding quota in a high-growth environment.

Methodology Driven:

You are disciplined in your approach, utilizing

MEDDPICC

(or a similar framework like Miller Heiman or Challenger) to qualify opportunities, identify champions, and expose the economic buyer early in the process.

Strategic Collaborator:

You know when to play the "Executive Card." You are skilled at looping in

Mortgage Automator leadership

at the right inflection points to build peer-level credibility and solidify the partnership on high-value deals.

Expert Communicator:

You don't just talk; you listen.



You can pivot your message based on the stakeholder and build lasting, trust-based relationships.

AI-Enabled:

You are tech-savvy and stay ahead of the curve, utilizing

AI tools like Claude

to gain an unfair advantage in prospecting and task management.

Disciplined Hunter:

You have a "founder's mentality" regarding your pipeline, maintaining 3-4x quota coverage through relentless and disciplined outbound activity.

Compensation and Benefits Mortgage Automator focuses on providing a simple and transparent pay structure based on experience and job-related skills. For this role, the median On-Target Earnings (OTE) is $140,000 - $180,000.

This represents your total expected annual compensation at 100% goal attainment, combining your guaranteed annual base salary with performance-based variable incentives. Our commission structures are uncapped, offering additional earning potential for performance exceeding targets.

Time Off & Work-Life Balance

Comprehensive Time Off: Enjoy a competitive paid vacation package designed to ensure you have the space to unplug and recharge throughout the year.

Holistic Wellness Leave: We provide dedicated personal leave that supports your total well-being, whether you need time for physical recovery or a mental health break.

Commuter-Friendly Hybrid: Versatile schedule that blends collaborative office time with the convenience of working from home.

Team Culture & Perks

Catered Lunches: Enjoy a monthly team lunch on the company to celebrate wins and connect with colleagues.

Growth & Learning: We foster a culture of continuous learning with internal opportunities for professional development.

Modern Workspace: A professional and supportive environment equipped with the tools and technology you need to succeed.

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📌 Sales Account Executive (Winnipeg)
🏢 Mortgage Automator
📍 Winnipeg