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Head of Customer Success

12 hours ago

Toronto, Ontario, Canada Loop Financial Full time $95,000 - $115,000

About The Role

Hi, I'm James, Head of Growth at Loop and I am hiring a Head of Customer Success to oversee our customer experience journey. 

This role is an onsite position at our downtown Toronto office (Adelaide and Spadina). 

Where You Come In

We are looking for a hands-on Head of Customer Success to lead our customer experience function across onboarding, support, and account management. This is an operational and customer-centric leadership position responsible for ensuring new and existing customers enjoy a world-class experience using Loop. You will be expected to play a player-coach role, dealing with customers directly while managing and building a team. This position is newly created to support our continued growth in customer success team.

You will manage and optimize the entire customer journey, through sign up, onboarding to customer support and account management. Your team will drive customer activation, retention, and satisfaction. Leading our burgeoning customer support and success team, you will be tasked with setting operational goals and KPIs, and continuously improving internal processes to uphold our commitment to customer excellence.

What You'll Be Doing

Customer Support:

  • Lead the customer support function, including ticket resolution, SLA adherence, and satisfaction measurement.
  • Actively participate in support workflows, especially for high-priority issues.
    Set and track KPIs for response time, resolution time, CSAT, NPS, and issue deflection.

Implementation & Onboarding:

  • Own and execute the end-to-end onboarding experience for new self-serve customers, ensuring smooth implementation and fast time-to-value.
  • Work directly with customers to gather necessary documentation, clarify requirements, and provide a delightful experience as they onboard to Loop.
  • Collaborate cross-functionally (Product, Engineering, Credit & Risk, Compliance, etc) to improve onboarding processes and resolve onboarding bottlenecks.

Account Management:

  • Act as a strategic partner for key accounts, providing proactive guidance and maintaining strong long-term relationships.
  • Lead initiatives to drive retention, increase product adoption and grow usage for all Loop customers.
  • Monitor account health, usage trends, and satisfaction to ensure continuous value delivery.
  • Continuously identify and share opportunities for product improvements.

Team Leadership & Strategy:

  • Directly manage members of the teams that are involved in customer support, onboarding and account management, including hiring, coaching, and performance management.
  • Define success metrics, team KPIs, and escalation protocols.
  • Create playbooks and processes to drive repeatability and efficiency across all customer touchpoints.

Success In This Role is 

  • Increase conversion rates from onboarding to activation.
  • Manage and grow the Loop's customer base.
  • Meet or exceed support SLAs and customer satisfaction benchmarks (e.g., NPS, CSAT).
  • Improve time-to-resolution and reduce onboarding duration through scalable processes.

Desired Qualities, Skills, and Experience

  • 5+ years in customer success, operations, or client services at a start-up. 
  • Proven experience managing teams in a high-growth environment.
  • Strong communication and relationship-building skills — you're at ease speaking directly with customers.
  • Metrics-driven mindset with a track record of hitting operational KPIs.
  • Deep empathy for customers, balanced with a pragmatic approach to prioritization and scale.

What's in it for you?

  • Opportunity to lead and shape a key function in a growing organization.
  • High-impact role with significant autonomy and ownership.
  • Supportive leadership and collaborative cross-functional team.
  • A chance to be part of a trailblazing team in a high-growth FinTech start-up.
  • Full support and training to ensure you meet your personal and professional goals.
  • A vibrant, collaborative startup culture that fosters innovation and growth.

What we offer

  • Salary range CAD$95,000-$115,000 annual, commensurate with experience 
  • Equity ranging % 
  • 3 weeks vacation 
  • Enrollment in group's health benefits after probation period 
  • This role is onsite in our downtown Toronto office
  • Kitchen full of snacks and drinks to keep you going throughout the day
  • Catered lunch on Fridays (we take recommendations)

Interview Process

  • 30 minutes video call to discuss the opportunity and the organization with Mandy, People and Business Operations Specialist 
  • 60 minutes in person meeting with two members of the Leadership team
  • Take home questionnaire 
  • 30 minutes in person meeting with Cato, CEO 
  • Background check and offer

How to Apply

To apply for this position, please click "apply" and share your resume, alongside a brief paragraph about yourself and your previous experience. Your application will be reviewed by our recruiters and hiring managers; we do not use AI tools for screening or selection.

Loop is committed to creating a diverse culture. We encourage you to apply regardless of who you are or where you came from - what matters is the journey ahead. Put simply, if you're unsure about your qualifications for this position, we'd still encourage you to apply