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

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.