Senior Customer Success Manager

About Mortgage Automator

Mortgage Automator is on a mission to revolutionize the lending industry by providing a comprehensive, end-to-end platform that eliminates the manual bottlenecks of private lending. Our innovative software empowers lenders to streamline their entire pipeline from origination and underwriting to automated servicing and investor reporting, so they can focus on scaling their business with confidence.

As one of the fastest-growing FinTech companies in North America, Mortgage Automator is customer-centric, ambitious, and deeply rooted in the lending community. We are building the "operating system" for private lenders, fostering a culture of ownership, high-speed execution, and decentralized decision-making.

The Role

We’re looking for a Senior Customer Success Manager to serve as a high-impact strategic partner to our most complex clients. In this role, you aren’t just managing a software subscription; you are transforming how private lenders operate. You will oversee a portfolio of high-value accounts, ensuring they transition from legacy manual processes to a fully optimized digital workflow.

As a Senior CSM, you are the bridge between a lender’s business objectives and our technical capabilities, driving long-term health, retention, and expansion.

Key Responsibilities

• Own the post-onboarding lifecycle for a portfolio of premium private lenders. You will be responsible for Net Revenue Retention (NRR), conducting Executive Business Reviews (EBRs) that align our platform’s roadmap with the client’s multi-year growth targets.
• Deeply analyze client operations to drive "stickiness." You will identify gaps in their usage of our Investor Portal, Automated Document Generation, and Servicing tools, consulting on how to reduce their Time-to-Fund and operational overhead.
• Proactively identify opportunities for account growth. You will partner with Sales to navigate renewals and upsell premium features, ensuring Mortgage Automator scales alongside the client’s assets under management (AUM).
• Act as the "Voice of the Customer" at the leadership level. You will synthesize market trends and client feedback into actionable insights for our Product and Engineering teams, influencing the future of mortgage technology.
• Mentor junior team members and contribute to the development of "Success Playbooks" that standardize excellence across the CS department.

Requirements

The Experience You Bring

To excel in this senior-level role, you must bring a sophisticated blend of financial acumen and consultative prowess:

• Lending & Finance Domain Expertise: You possess a deep understanding of the private lending lifecycle (origination, underwriting, draw management, and servicing). You can talk shop with lenders about interest reserves, loan-to-value (LTV) ratios, and investor distributions without skipping a beat.
• Strategic Relationship Management: You have a proven track record of building "trusted advisor" relationships with C-Suite executives and Principals. You are comfortable navigating high-stakes conversations and managing the expectations of sophisticated financial stakeholders.
• Analytical Mindset: You are data-driven. You can analyze usage metrics and financial KPIs to build a compelling narrative for the client, proving the ROI of our platform through hard evidence rather than anecdotes.
• Executive Communication: You possess the "gravitas" to lead a room. Whether it's a technical deep-dive or a high-level strategic pitch, your communication is clear, concise, and tailored to your audience.
• Problem-Solving Agility: You thrive in the "grey area." When a client has a unique lending structure, you have the creativity and technical aptitude to map their complex needs to our software’s capabilities.

Qualifications

• 5+ years of experience in Customer Success, Account Management, or Consulting, specifically within FinTech, PropTech, or Private Lending.
• Proven experience managing a book of business exceeding $1M+ in ARR.
• Expert-level proficiency in Salesforce or HubSpot, with an ability to leverage CRM data for proactive outreach.
• Strong understanding of the North American mortgage landscape and regulatory environment.

This Role is NOT for you if: 

• You prefer a reactive "support ticket" environment; we are looking for proactive strategists.
• You find the complexities of financial workflows and lending math tedious.
• You prefer a rigid, siloed corporate structure over a fast-paced, "all-hands-on-deck" startup environment.

Benefits

Why Join Us? 

At Mortgage Automator, you’ll have a seat at the table in one of Canada’s most exciting FinTech success stories. We offer a competitive salary, performance-based bonuses, a flexible hybrid work environment, and the opportunity to truly own your impact in an industry ripe for disruption.

Compensation and Benefits

Mortgage Automator focuses on providing a simple and transparent pay structure based on experience and job-related skills. For this role, the annual On-Target-Earnings (OTE) ranges from $80,000 - $100,000.

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: 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.