Sales Account Executive

Mortgage Automator Inc.; Toronto; Hybrid; CAD 195,000 - 250,000; Full time

Benefits offered by this job

Catered lunches

Growth & learning

Modern workspace

Job summary

Mortgage Automator is seeking a high-caliber Account Executive to own the full opportunity cycle—from first cold touch to multi-year closing—targeting mid-market private lending orgs across North America.

You will drive strategic outbounding, leverage AI tools, and navigate complex multi-stakeholder deals to secure buy-in and growth.

Qualifications

• 2–4 years of software sales experience.
• Proven track record of meeting or exceeding quota.
• Experience in high-growth SaaS environments.
• Experience with MEDDPICC or similar frameworks.

Responsibilities

• Full Cycle Ownership: own everything from targeted outbound prospecting to discovery, demo, and closing.
• Strategic Outbounding: build pipeline with targeted accounts; leverage AI tools like Claude for research.
• Value-Based Discovery: uncover business impacts through active listening and guiding decisions.
• Complex Deal Navigation: align IT, Operations, Finance to secure buy-in.
• Contract Negotiation: negotiate multi-year pricing models and packaging.
• Urgency & Momentum: create genuine urgency and maintain momentum through long sales cycles.

Skills

Value-based selling

Hunter mentality

MEDDPICC framework

C-suite engagement

Negotiation skills

Outbound prospecting

Tools

Claude AI

CRM

Job description

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: Flexible 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.