Our Journey at Keep

At Keep, we embarked on a mission with a powerful question: Why hasn't the banking experience caught up with the rapid pace of technology?

This continues to fuel our passion for reshaping the Canadian fintech landscape. We provide businesses with a comprehensive suite of cross-border banking services, offering everything from credit cards to deposit accounts, currency conversions, and revenue financing.

With a team of seasoned global startup veterans with successful exits, Keep is committed to leading the charge as Canada's next-generation fintech institution. Backed by VCs in the fintech sector, we're racing ahead, expanding our reach and impact like never before.

About the Role

Join Keep as a Customer Support Representative and play a key role in delivering thoughtful, high-quality support in a fintech environment where accuracy, judgment, and clear communication matter.

In this role, you will support customers primarily through written tickets and emails, with phone calls making up a smaller but important part of the workload. Whether a customer reaches out by email or phone, the expectation is the same: you’ll take ownership of the issue, investigate thoughtfully, communicate clearly, and guide the customer toward a practical and satisfactory resolution.

This is an entry-level role designed for someone with strong fundamentals and sound judgment. While you’ll be supported with documentation, training, and team collaboration, you’ll also be trusted to think critically, ask the right questions, and make decisions within scope. Over time, you’ll grow into handling the majority of cases independently, including more complex and nuanced situations.

Who We’re Looking For

• You have at least 1–2 years of experience in customer support or a similar customer-facing role, ideally, but not exclusively, in a startup, fintech, or evolving environment focused on continuous improvement.

• You’re comfortable working in an environment where products and processes evolve over time, and you’re able to quickly understand changes and apply them with care and precision.

• You communicate clearly and confidently, both in writing and on calls. You’re comfortable explaining complex topics in a calm, human way.

• You enjoy problem-solving and investigation, and you’re willing to spend the time needed to fully understand an issue rather than rushing to a surface-level answer.

• You’re comfortable handling ambiguity and know when to move forward independently and when to ask questions or loop in the right team.

• You take ownership of your work and care about accuracy, customer trust, and doing things the right way.

• You’re detail-oriented and thoughtful, especially when working with financial information that directly impacts customers.

• You’re open to learning and feedback, and you approach growth with curiosity, accountability, and a willingness to refine your approach over time.

We value thoughtful investigation over fast replies — taking extra time to get it right is always preferred over responding quickly with incomplete information.

Key Responsibilities

Handle Customer Cases End-to-End:

Respond to customer inquiries primarily through tickets and emails, with occasional phone calls, taking ownership of issues from initial contact through resolution.

Investigate and Resolve Issues:

Review account data, transactions, system behavior, and internal tools to understand what’s happening and provide accurate, well-reasoned responses.

Communicate Clearly and Empathetically:

Deliver responses that are structured, calm, and human, especially in situations involving stress, urgency, or financial impact.

Exercise Sound Judgment:

Know when an issue can be resolved within scope, when partial solutions are appropriate, and when escalation is necessary. Escalate thoughtfully, with detailed context and clear findings, and apply policy consistently while communicating outcomes clearly and humanely.

De-escalate and Set Expectations:

Handle emotionally charged interactions professionally, guiding customers toward realistic outcomes without defaulting to escalation or deflection.

Collaborate Across Teams:

Work with internal partners such as Engineering, FinOps, Compliance, and Collections to resolve edge cases and improve processes.

Contribute to Continuous Improvement:

Identify recurring issues, unclear processes, or gaps in documentation, and provide constructive feedback to help improve operations, SOPs and the overall support experience.

Growth and Development

This role is designed to grow with you.

Within your first 3–6 months, you’ll be expected to:

Handle at least 80% of customer cases independently.

• Confidently identify edge cases and know where to escalate them efficiently.

• Provide thoughtful input on process improvements and documentation.

• Develop strong product and operational knowledge across Keep’s platform.

Support, training, and mentorship are provided throughout, but growth also comes from engagement, curiosity, and ownership.

As you grow, you’ll be trusted with increasing autonomy and expected to apply sound judgment while knowing when to pause, ask questions, or escalate thoughtfully.

Why You Should Be Excited About This Role

• Work on meaningful, real-world problems that directly affect customers’ finances.

• Be trusted to think, investigate, and communicate rather than follow scripts.

• Gain deep exposure to fintech operations, banking systems, and cross-functional collaboration.

• Join a team that values quality, judgment, and thoughtful customer experience over raw volume.

Grow into a well-rounded support professional with strong investigative and communication skills.

Why This Might Not Be a Good Fit

If you prefer highly scripted workflows or constant step-by-step direction, this role may feel uncomfortable.

• If you’re looking for a high-volume, low-complexity call-center environment, this will not be a match.

• If ambiguity feels stressful rather than interesting, the investigative nature of this role may be challenging.

If you prefer to work in isolation without collaboration or feedback, this team may not be the right fit.

What the Interview Process Looks Like

1. Initial screening with our AI platform (TalentLlama)

2. Conversation with our People team

3. Copy challenge to assess written communication and clarity

4. Interview with the Customer Support Lead & Manager

5. Practical case discussion focused on problem-solving and judgment

6. References

7. Offer 🎉

Want to Learn More?

Head over to our webpage to discover more about us. Take a peek at our Glassdoor profile to see what our Keepers are saying, and stay tuned for exciting updates on our LinkedIn page and learn about our values and benefits on our career page.

Commitment to Diversity and Inclusion

Keep provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.