Top Benefits
About the role
Job Summary
We're looking for a driven, consultative Mid-Market Account Executive to own the full sales cycle — from prospecting to close — targeting private lending organizations across North America. You'll sell a purpose-built Loan Origination and Servicing SaaS platform that helps lenders modernize operations and scale their portfolios.This is a hunter role for someone who thrives outbound, builds trust with financial services decision-makers, and navigates complex, multi-stakeholder deals with precision.
Job Description
- Own outbound prospecting — identify, research, and engage mid-market private lending companies through targeted outreach.
- Run a structured sales process — qualify opportunities, uncover pain, map the buying committee, and drive deals to close.
- Manage a full sales cycle — from first contact through discovery, demo, proposal, negotiation, and contract execution.
- Build executive relationships — engage with C-suite and senior stakeholders within target accounts.
- Develop territory plans — build and maintain a healthy pipeline of 3–4x quota coverage through disciplined outbound activity.
- Collaborate cross-functionally — work closely with Sales Engineering, Customer Success, and Marketing to deliver a world-class buying experience.
- Forecast accurately — maintain up-to-date CRM hygiene and provide reliable weekly/monthly forecasts to sales leadership.
- Be a market expert — develop a deep understanding of the private lending landscape, buyer pain points, competitive alternatives, and industry trends.
Requirements
- 3–6 years of B2B sales experience.
- Proven track record of consistent quota attainment.
- Experience managing complex, multi-stakeholder sales cycles .
- Strong discovery and qualification skills (MEDDPICC or similar).
- Excellent communication and executive presence — comfortable presenting to senior financial services leaders.
- Self-starter mentality with strong organizational and time management skills.
Benefits
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: 4 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.
Not the right fit? Search for Sales Account Executive jobs in Toronto
About Mortgage Automator
Named the Supplier/Innovator of the Year 2019 by the Mortgage Awards of Excellence. Mortgage Automator is the most advanced end-to-end loan origination and servicing software for private lenders. Perfect for residential, commercial, and construction lending (rehab, fix & flips), in seconds, it auto-generates custom documents, compliance reports, ACH/PAD payments, and more. Improve communication with borrower and investor portals. With unlimited documents, training, and support, focus your team on growth and let Mortgage Automator handle the rest.
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Top Benefits
About the role
Job Summary
We're looking for a driven, consultative Mid-Market Account Executive to own the full sales cycle — from prospecting to close — targeting private lending organizations across North America. You'll sell a purpose-built Loan Origination and Servicing SaaS platform that helps lenders modernize operations and scale their portfolios.This is a hunter role for someone who thrives outbound, builds trust with financial services decision-makers, and navigates complex, multi-stakeholder deals with precision.
Job Description
- Own outbound prospecting — identify, research, and engage mid-market private lending companies through targeted outreach.
- Run a structured sales process — qualify opportunities, uncover pain, map the buying committee, and drive deals to close.
- Manage a full sales cycle — from first contact through discovery, demo, proposal, negotiation, and contract execution.
- Build executive relationships — engage with C-suite and senior stakeholders within target accounts.
- Develop territory plans — build and maintain a healthy pipeline of 3–4x quota coverage through disciplined outbound activity.
- Collaborate cross-functionally — work closely with Sales Engineering, Customer Success, and Marketing to deliver a world-class buying experience.
- Forecast accurately — maintain up-to-date CRM hygiene and provide reliable weekly/monthly forecasts to sales leadership.
- Be a market expert — develop a deep understanding of the private lending landscape, buyer pain points, competitive alternatives, and industry trends.
Requirements
- 3–6 years of B2B sales experience.
- Proven track record of consistent quota attainment.
- Experience managing complex, multi-stakeholder sales cycles .
- Strong discovery and qualification skills (MEDDPICC or similar).
- Excellent communication and executive presence — comfortable presenting to senior financial services leaders.
- Self-starter mentality with strong organizational and time management skills.
Benefits
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: 4 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.
Not the right fit? Search for Sales Account Executive jobs in Toronto
About Mortgage Automator
Named the Supplier/Innovator of the Year 2019 by the Mortgage Awards of Excellence. Mortgage Automator is the most advanced end-to-end loan origination and servicing software for private lenders. Perfect for residential, commercial, and construction lending (rehab, fix & flips), in seconds, it auto-generates custom documents, compliance reports, ACH/PAD payments, and more. Improve communication with borrower and investor portals. With unlimited documents, training, and support, focus your team on growth and let Mortgage Automator handle the rest.