[Hiring] Staff Customer Experience Strategist @Plooto

Role Description

We are looking for a Staff Customer Experience Strategist to help shape how Plooto delivers a seamless and trusted experience across the customer journey. Reporting to the VP, Risk & Operations , this is a highly influential individual-contributor role with the opportunity to work across Product, Engineering, Operations, Risk, Data, Finance, and GTM to solve some of our most important customer and business problems.

This role owns Customer Experience Insights and Optimization :

• Uncovering what drives customer contact and product/operational churn.
• Diagnosing the underlying payment, product, and process issues.
• Turning insights into action.
• Identifying improvements through tooling, automation, AI, or process changes.
• Recognizing where deeper Product or Engineering investment can create meaningful impact.

You will bring together:

• Deep customer understanding.
• Payments expertise.
• Hands-on data analysis.
• Strong business judgment.

These will help uncover root causes, quantify customer and business impact, and translate insights into clear recommendations that drive measurable improvement.

Qualifications

• Significant experience in payments, fintech, SaaS, customer experience strategy, or a related analytical role, ideally in a product-led environment.
• Strong understanding of how money moves through a payments business, including funding, settlement, returns, reconciliation, risk reviews, recalls, cross-border payments, chargebacks, and exceptions.
• Demonstrated track record of using data to identify and solve systemic customer, product, or operational problems, with measurable improvements in areas such as contact rate, churn, onboarding, payment transparency, or cost-to-serve.
• Strong hands-on data proficiency using SQL, Databricks, Salesforce, and similar tools, with minimal reliance on Data for routine analysis.
• Strong first-principles problem solving and business judgment, with the ability to move from signal → driver → root cause → opportunity → recommendation and connect insights to customer and business impact.
• Experience building or materially improving a customer experience or friction-reduction capability, including using AI, automation, tooling, and process improvements to create measurable impact.
• Strong cross-functional influence and communication skills, with the ability to build alignment through clear problem framing, evidence, sound judgment, and concise, decision-ready recommendations for Product and senior leaders.

Benefits

• Transforming the payments space in North America by delivering an unrivalled product experience.
• Addressing poor financial management and cash flow issues for small businesses.
• Strong product-market fit and a massive opportunity ahead.
• Backing of experienced fintech leaders.
• Joining a team that cares deeply about customer impact and takes pride in their craft.
• Opportunity to shape the next chapter of Plooto's growth story.

Company Description

Plooto is a payment automation platform built to help accountants, bookkeepers, and their clients take control of their payables and receivables. Our customers range from busy entrepreneurs to finance teams and non-profits, with a strong footprint among accounting firms and bookkeeping professionals across Canada.