Staff Customer Experience Strategist

About Plooto: Plooto is a payment automation platform designed for accountants, bookkeepers, and their clients to manage payables and receivables efficiently. It offers approval workflows, audit trails, bulk payments, and automated reconciliation, saving time and ensuring financial accuracy. Customers range from entrepreneurs to finance teams and non-profits, with a strong presence among accounting firms and bookkeeping professionals across Canada.

About the Role

We are seeking a Staff Customer Experience Strategist to enhance Plooto’s customer experience across the entire journey. Reporting to the VP, Risk & Operations, this role involves collaborating with Product, Engineering, Operations, Risk, Data, Finance, and GTM teams to address critical customer and business challenges.

This position focuses on Customer Experience Insights and Optimization, including identifying drivers of customer contact and churn, diagnosing underlying issues in payments, product, and processes, and translating insights into actionable improvements. You will determine quick wins through tooling, automation, AI, or process changes, as well as identify opportunities requiring deeper Product or Engineering investment.

You will combine deep customer understanding, payments expertise, hands-on data analysis, and strong business judgment to uncover root causes, quantify customer and business impact, and develop clear recommendations for measurable improvements.

What You’ll Do

• Uncover the biggest opportunities to improve the customer journey. Analyze customer contacts, churn, payment behavior, operational data, reviews, and NPS/CSAT to identify friction points and prioritize high-impact opportunities.
• Diagnose what is driving the experience. Investigate root causes related to product, payment, process, policy, tooling, or integration issues, and define key outcomes.
• Shape customer experience priorities across SaaS and payments. Identify friction in product workflows, payment flows, and operational processes, and define customer and business outcomes for improvement.
• Turn data into decisions. Test hypotheses, segment customers, quantify impact, and connect insights to contact rates, churn, revenue retention, and cost-to-serve.
• Create momentum now while shaping what comes next. Identify opportunities for AI, automation, tooling, communications, and process improvements, while partnering with Product and Engineering on deeper product investments.
• Influence high-value improvements across Plooto. Use strong problem framing, evidence, and clear target outcomes to align with Product, Engineering, Customer Operations, Risk, Data, Finance, and GTM teams.
• Build a stronger Customer Experience capability. Enhance how Plooto measures and acts on customer insights, create reliable visibility into contact and churn drivers, and translate complex analyses into concise, decision-ready recommendations for senior leaders.

What We’re Looking For

• Significant experience in payments, fintech, SaaS, customer experience strategy, or related analytical roles, ideally in a product-led environment.
• A strong understanding of how money moves through a payments business, including funding, settlement, returns, reconciliation, risk reviews, recalls, cross-border payments, chargebacks, and exceptions.
• A 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.