Customer Success Operations Specialist

Ready to accelerate your career?
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 We’re a small but mighty team transforming how businesses manage vehicle reimbursement — replacing outdated programs with smart, automated solutions.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 looking for a Customer Success Operations Specialist to strengthen how we equip our customer-facing teams and educate our customers. You’ll connect Customer Success, Product, Support, Implementation and Product Marketing, making sure product changes are understood, customer questions are heard, and the right training and communications reach the right people. This is an operations and enablement role. Your focus will be building repeatable processes, resources and communications that help the whole CS team succeed.
What you’ll do
Meet with Product at the end of each sprint to understand what has been completed, when it will be released and which customers will benefit
Translate release notes into practical training for CS and Support, including feature demonstrations, customer use cases, talking points and answers to likely questions
Help CSMs explain the value of new features and identify opportunities to introduce them to existing customers
Monitor questions from CSMs and customer admins to spot knowledge gaps, then develop group training, individual coaching or resources to address them
Regularly review and verify internal documentation in Guru so customer-facing teams can rely on it
Plan and manage communications to drivers, admins and customer contacts, using Mailchimp to reach the right audiences with clear, timely information
Demonstrate new features to existing customers through webinars or other training sessions, and answer questions about how to use them
Partner with Product Marketing to create customer enablement materials, including emails, webinars, guides and certifications
Share customer insights with Product Marketing to help shape customer campaigns, then brief the CS team on upcoming campaigns and how they can use them in customer conversations
Work with the Implementation Specialist to develop live and self-serve training, using tools such as Loom and Navattic where appropriate
Work with Support to identify ticket trends by program type, customer segment and account, and translate those trends into useful insights for CS and Product
Bring recurring customer questions, feedback and adoption barriers to Product as a trusted voice of the customer
Turn repeated questions into practical resources, such as videos, guides and one-pagers, and improve those resources based on how teams and customers use them
What you bring
3-5 years of experience in Customer Success Operations, customer enablement, customer education or a related role
The ability to learn a product in depth and explain complex features in clear, useful language for internal teams and customers
Experience developing and delivering training, product demonstrations and written enablement materials
Hands-on experience with Mailchimp or a similar platform for building, segmenting and sending customer communications
Strong writing, facilitation and project management skills, with the ability to coordinate work across several teams
Comfort using customer feedback, support trends and recurring questions to decide where training or documentation is needed
Experience with knowledge and training tools such as Guru, Loom or Navattic is an asset
Hands-on experience with Customer Success and Support tools such as Gainsight, Zendesk, and Hubspot is an asset
Compensation:
In line with Ontario’s Pay Transparency legislation, the expected base compensation for this role is $75,000–$90,000 CAD annually (dependent on experience and competency). 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.
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.