Head of Sales (B2B Saas)

About Mortgage Automator:

Built by Lenders, Designed for Growth. Mortgage Automator was started in 2013 as a simple document generating tool for a small private lender in Toronto, Canada. Since then, the software has evolved significantly to encompass every possible feature and account for all the unique lending scenarios. Mortgage Automator is a cutting-edge technology company specializing in providing innovative, automated solutions for the private lending industry.

Our comprehensive product offerings include modules for loan origination, servicing, and administration. The loan origination module automates the entire process from application to approval, ensuring quick and accurate decision-making. Our servicing module streamlines payment processing, accounting, and borrower communications, while our administration tools offer robust reporting, compliance tracking, and portfolio management capabilities, optimizing operations for our clients.

At Mortgage Automator, our mission is to transform the private lending landscape through the power of automation and technology. We are committed to reducing administrative burdens, improving operational efficiency, and enhancing clarity throughout the lending process. By delivering exceptional support and training, we ensure our clients maximize the value of our platform, empowering them to succeed in a competitive market and driving growth and innovation within the industry.

Why Join Us?

• Competitive Compensation & Benefits – Industry-leading pay, full health benefits, generous vacation
  
• High Impact – You’ll directly influence pipeline, sales success, and revenue growth
  
• Tech-Forward Culture – Work with the latest tools in automation, analytics, and performance marketing
  
• Industry Growth – Join a company scaling fast in a specialized fintech vertical
  
• Collaborative Team – Work directly with the senior leadership team, and across all cross-functional stakeholders
  

Role Overview & Key Responsibilities:

As Head of Sales, you will own the revenue function, lead a growing team of AEs, and be accountable for scaling our sales engine across North America. You’ll drive pipeline growth, oversee full-funnel performance, and embed operational excellence into every stage of the customer journey.

• Own Sales Operations & Activity Management: Drive consistent execution by defining and enforcing daily, weekly and monthly activity standards (calls, emails, demos, follow-ups), and by conducting regular one-on-ones to review each rep’s pipeline, deal progression and next steps.
  
• Ensure CRM Excellence: Hold the team accountable for timely, accurate CRM data entry, contact updates, deal stages, notes and follow-up tasks to guarantee reliable forecasting and seamless handoffs. Work with the broader executive team to design and refine sales processes across the sales and client journey, including Hubspot and activity management to maximize efficiency and effectiveness.
  
• Monitor Pipeline Health & Forecast Accuracy: Lead structured pipeline reviews with each rep and the broader leadership team; identify at-risk deals, emerging bottlenecks or coverage gaps, and implement corrective action plans.
  
• Coach & Calibrate in Real Time: Shadow calls and demos, provide on-the-spot feedback, conduct call calibrations and role-play sessions; embed best practices for discovery, objection handling and closing.
  
• Set Clear Metrics & Accountability: Define key performance indicators (KPIs) for activity, conversion rates and revenue attainment; publish dashboards and scorecards; deliver transparent reporting to the executive team.
  
• Drive Continuous Learning & Improvement: Partner with training and enablement to develop onboarding programs, ongoing skills workshops and refresher training; champion Change Management of new tools, processes and playbooks.
  Design and maintain SOPs and sales playbooks that align with our evolving product and GTM strategy.
  
• Collaborate Across Functions: Work closely with all departments and teams to ensure that sales teams are equipped and to align GTM efforts across the organization. 
  • Work collaboratively with Product (roadmap feedback), Marketing (demand gen), Onboarding & Customer Success (hand-offs & churn prevention), along with other teams., and other teams.
    
  • Provide structured feedback from the market to inform product roadmap and positioning. Inform product roadmap through insights from prospects, churn feedback, and win/loss analysis.
    
• Scale & Build the Team: Recruit high-caliber sales professionals, structure pods or territories for optimal coverage, and foster a culture of ownership, curiosity and relentless execution.
  
  

Qualifications:

• Track Record of scaling B2B SaaS revenue and in building and leading successful sales teams within the SaaS or technology sector.
  
• Minimum of 5–7 of previous experience specific to building and leading quota-carrying SaaS AE’s and sales people, with at least  5 years in a leadership role
  
• Hands-on proficiency with CRM platforms (HubSpot preferred) and associated metrics dashboards, sales tools and platforms. 
  
• Data-driven approach to forecasting, pipeline management & reporting, with comfort defining KPIs, building dashboards, and presenting to exec teams
  
• Strong coaching & people-management skills, including experience running ride-along demos, call calibrations, one-on-ones, and performance improvement plans
  
• Experience designing and optimizing repeatable sales processes, playbooks, and qualification frameworks (MEDDIC, BANT, SPICED, etc.)
  
• Demonstrated ability to recruit, onboard & retain top sales talent, building a culture of accountability, continuous learning, and high morale
  

• Skilled in developing and executing training programs, SOPs, and change management rollouts.
  
• Analytical and process-driven; comfortable working with KPIs, conversion metrics, and performance dashboards.
  
• Sold complex, multi-module platforms (ideally FinTech, Lending, or ERP)
  
• Comfortable rolling up sleeves—this is a “doer,” not only a strategic leadership role. 
  

Bonus Qualifications (not required):

• Experience in private lending, LOS, or mortgage technology platforms
  
• Mortgage/Real Estate business, including agent, broker licenses etc.
  
• Familiarity with regulatory, compliance, and reporting in lending environments

Role Details:

• Location: Toronto (In-office)
  
• Type: Full-time, Permanent
  
• Schedule: Monday–Friday