Head of Customer Success

Role Overview & Key Responsibilities

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 platform 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)

Team Leadership & Development

• 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

Retention, Expansion & Advocacy

• 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

• Implement tech-touch strategies,
• onboarding tours, and in-app education
• Work within and optimize HubSpot for
• customer lifecycle management
• Ensure strong data hygiene, usage
• tracking, and CRM health across all CS workflows

Cross-Functional Collaboration

• 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

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Requirements

• 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.
• SaaS Expertise: Proven experience scaling a CS function in a B2B SaaS environment with a complex platform (FinTech/lending/ERP a plus)
• Product-Led Thinking: Deep understanding of customer journeys, lifecycle metrics, and tech-enabled CS strategy●
• Tools Savvy: Proficient with CS and CRM tools, HubSpot (preferred), in-app guidance tools, and feedback collection platforms
• Analytical & Operational: Skilled at building dashboards, defining KPIs, tracking retention/churn/expansion metrics
• Client-Facing Acumen: Strong interpersonal and communication skills, capable of holding strategic conversations with executives and clients
• Builder Mentality: Able to roll up sleeves to create from scratch, whether that’s processes, teams, leveraging and implementing automation and AI, dashboards, or SOPs

Benefits

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.