As Head of Customer Success, you will build, lead, and scale the Customer Success function at Mortgage Automator. You will serve as a strategic partner across Product, Sales, Onboarding, Support, and Marketing, working cross-functionally to drive customer value, retention, and lifetime expansion. You will be the client advocate and help to design the frameworks, systems, and team culture that ensures customers succeed with our p latform and become long-term advocates.

Customer Success

Strategy & Execution Design, implement, and own the end-to-end customer success strategy Build customer journey maps, segment strategies, and health scoring models Develop and deploy scalable playbooks across lifecycle stages (adoption, renewal, upsell, advocacy) Build and manage a high-performing CS team, starting with CSMs Define KPIs, compensation frameworks, SOPs, and coaching cadences Lead regular 1-on-1s, performance reviews, and growth development sessions Reduce churn by proactively managing customer risk and engagement Collaborate with Product and Support to resolve issues before they escalate Drive account expansion via contextual upsells (integrations, packages, add-ons) Support Marketing with review generation (G2, Capterra, Serchen) and success story development Product Collaboration & Customer Insights Serve as the primary voice of the customer to Product and Development Build and manage structured feedback loops (feature requests, pain points, UX friction)



Leverage data and usage patterns to guide roadmap recommendation Automation, Systems & Data Integrity Work within and optimize HubSpot for customer lifecycle management Ensure strong data hygiene, usage tracking, and CRM health across all CS workflows Partner with Sales and Onboarding to ensure smooth handoffs and accurate customer expectations Align with Onboarding on customer readiness and early experience metrics Work with Marketing to define ICPs and gather actionable user insights Collaborate with Support/Client Solutions on client escalations and ticket trends #Leadership Experience: 5 - 7 years in Customer Success or very similar, including 3+ years in a senior leadership/head-level role in a SaaS company in CS, Onboarding or very similar. Product-Led Thinking: Deep understanding of customer journeys, lifecycle metrics, and tech-enabled CS strategy â Tools Savvy: Proficient with CS and CRM tools, HubSpot (preferred), in-app guidance tools, and feedback collection platforms Skilled at building dashboards, defining KPIs, tracking retention/churn/expansion metrics Mortgage Automator was started in 2013 as a easy 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.

📌 Customer Success (Toronto)
🏢 Lucas James Talent Partners
📍 Toronto