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Director, Customer Success

Canada - Remote

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Cardata is where driven people make an outsized impact. We’re a small but mighty team transforming how businesses manage vehicle reimbursement — replacing outdated programs with smart, automated solutions.

Our vision is bold: to provide the most comprehensive, intelligent, and automated software and services for creating ideal vehicle programs. And we’re building toward that vision every single day.

Join us and you’ll find challenge, growth, and the chance to deliver real impact — helping hundreds of companies and thousands of drivers across North America focus on the work that matters most to them.

Cardata is seeking an experienced Director of Customer Success to lead our Customer Success, Implementation, and Customer Success Operations functions through the company’s next stage of growth.

Reporting to the Chief Customer Officer, this leader will be accountable for the performance and development of our Customer Success Managers, Implementation Specialist, and Customer Success Operations Specialist. The Director will ensure customers achieve measurable value, implementations are executed successfully, risks are addressed proactively, and the team operates with clear expectations and accountability.

This is a hands-on leadership role for someone who can think strategically while remaining close to execution. The ideal candidate is comfortable building structure in a growing organization, prioritizing to avoid capacity constraints, and finding creative ways to improve results with available resources.

The Director will also help advance Cardata’s use of AI, automation, reporting, and customer insights to improve team efficiency and customer outcomes.

What you will do

  • Lead, coach, and develop the Customer Success, Implementation, and Customer Success Operations teams.
  • Establish clear performance expectations, operating cadences, and accountability across the organization to drive customer adoption, value realization, executive engagement, retention, and renewal readiness.
  • Ensure customer risks are identified early and supported by actionable recovery plans.
  • Provide executive sponsorship for strategic, complex, and at-risk customer relationships.
  • Oversee the new-customer implementation experience, including launch quality, time-to-value, training, and handoff into Customer Success.
  • Partner with Customer Success Operations to improve CSM enablement, reporting, portfolio insights, data quality, workflows, and the Customer Success knowledge base.
  • Use customer and operational data to identify trends, prioritize action, and provide clear recommendations to executive leadership.
  • Identify opportunities to simplify processes, automate manual work, and return capacity to strategic customer engagement.
  • Establish practical expectations for how AI should be used across Customer Success to improve preparation, analysis, communication, and workflow efficiency.
  • Partner closely with Account Management, Support, Sales, Product, Engineering, Finance, and Operations.
  • Represent the customer perspective in company planning and product-prioritization discussions.
  • Build a high-performance culture grounded in ownership, sound judgment, transparency, and continuous improvement.

What you bring

  • 8+ years of experience in Customer Success, customer operations, implementation, account leadership, or a related SaaS function.
  • 4+ years of people leadership experience, including coaching and holding experienced customer-facing professionals accountable.
  • Demonstrated success improving customer retention, adoption, health, and team performance.
  • Experience leading teams through organizational growth, operational change, or evolving processes.
  • Strong ability to prioritize, simplify work, and improve outcomes in a resource-conscious environment.
  • Experience establishing Customer Success operating cadences, performance measures, and scalable processes.
  • Strong strategic account management and executive customer engagement experience.
  • Experience leading or closely partnering with Implementation and Customer Success Operations.
  • Ability to turn reporting and customer data into meaningful insights and action.
  • Strong cross-functional leadership skills, particularly with Sales, Account Management, Product, Engineering, Support, and Finance.
  • Practical experience using AI and automation to improve personal productivity, team effectiveness, or customer workflows.
  • Strong executive communication, analytical thinking, judgment, and follow-through.
  • Experience with Gainsight, Salesforce, HubSpot, or a comparable Customer Success or CRM platform; Gainsight experience is a plus.

Who you are

  • A strong people leader who sets clear expectations and addresses performance directly and fairly.
  • Strategic enough to define the future state and practical enough to build it step by step.
  • Resourceful and comfortable operating with less while making a thoughtful case for future investment.
  • Data-informed without losing sight of customer context and human judgment.
  • Curious and confident using AI to improve the way work gets done.
  • Highly collaborative and able to influence teams outside your direct authority.
  • Comfortable leading through ambiguity, change, and competing priorities.
  • Passionate about developing teams and creating exceptional customer outcomes.

Compensation:

In line with Ontario’s Pay Transparency legislation, the expected base compensation for this role is $115,000-135,000 CAD annually, with actual earnings dependent on experience, skills, and performance.This is a vacant position, and we are hiring with intention and seeking someone who will bring new perspective, contribute meaningfully to the team, and grow with the organization.

 

Why you’ll love working at Cardata:

We’ll be honest — Cardata isn’t for everyone. If you thrive in a fast-paced environment, take extreme ownership, and constantly push yourself (and your work) to be the best, you’ll fit right in.

You’ll be surrounded by driven teammates who genuinely care — about the work, about our customers, and about helping each other succeed. Together, we take on ambitious goals and celebrate the wins along the way.

What we offer in return for you bringing your best:

  • Remote work and flexible working hours
  • Mentorship and development opportunities (to help you achieve your career goals!)
  • Extended medical & dental benefits
  • Healthcare spending account
  • $3,000 annual Health and Wellness Spending Account to support your overall wellbeing
  • Employee assistance program (EAP)
  • Flexible (Unlimited) Time Off: No annual cap on vacation, supported by a trust-based, flexible approach to time away.

Cardata is an equal opportunity employer. All candidates will be equally considered without regard to race, ancestry, place of origin, colour, ethnic origin, language, citizenship, creed, religion, gender/gender identity, sexual orientation, age, marital status, physical and/or mental handicap or financial ability. We are dedicated to creating an inclusive environment where everyone feels welcome to bring their authentic selves to work.

If you require accommodations during the recruitment process, please let us know.

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