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Plooto is a payment automation platform helping accountants, bookkeepers, and their clients manage payables and receivables through approval workflows, audit trails, bulk payments, and automated reconciliation. The company serves busy entrepreneurs, finance teams, non-profits, and accounting firms across Canada.
You will join as Staff Customer Experience Strategist, reporting to the VP of Risk & Operations. This is a highly influential individual-contributor role working across Product, Engineering, Operations, Risk, Data, Finance, and GTM to solve critical customer and business problems.
Your core responsibility is owning Customer Experience Insights and Optimization: uncovering what drives customer contact and churn, diagnosing underlying payment, product, and process issues, and translating insights into action. You will identify quick wins through tooling, automation, AI, or process changes, and surface opportunities requiring deeper Product or Engineering investment.
Key responsibilities include:
- Analyzing customer contacts, churn, payment behavior, operational data, reviews, and NPS/CSAT to identify friction and high-impact opportunities
- Diagnosing root causes across product workflows, payment flows, operational processes, policies, tooling, and integrations
- Shaping customer experience priorities across SaaS and payments domains
- Testing hypotheses, segmenting customers, and quantifying impact on contact rate, churn, revenue retention, and cost-to-serve
- Identifying opportunities for AI, automation, tooling, and process improvements while partnering with Product and Engineering on structural investments
- Building cross-functional alignment across Product, Engineering, Customer Operations, Risk, Data, Finance, and GTM through clear problem framing and evidence-based recommendations
- Evolving Plooto's customer experience measurement and insights capability, creating visibility into contact and churn drivers, and translating complex analysis into decision-ready recommendations for senior leaders
Success means systematically reducing avoidable customer contact, product- and operationally-driven churn, and cost-to-serve; improving visibility into friction root causes; identifying and implementing automation and AI opportunities; creating effective interim solutions while product improvements develop; and ensuring customer insights translate into clear, prioritized opportunities for teams.
REQUIREMENTS:
- Significant experience in payments, fintech, SaaS, customer experience strategy, or related analytical roles, ideally in product-led environments
- 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 using data to identify and solve systemic customer, product, or operational problems with measurable improvements in contact rate, churn, onboarding, payment transparency, or cost-to-serve
- Strong hands-on data proficiency with SQL, Databricks, Salesforce, and similar tools, with minimal reliance on Data teams for routine analysis
- Strong first-principles problem solving and business judgment, able 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, able to build alignment through clear problem framing, evidence, sound judgment, and concise, decision-ready recommendations for Product and senior leaders
