Staff Customer Experience Strategist

About Plooto

Plooto is a payment automation platform built to help accountants, bookkeepers, and their clients take control of their payables and receivables. From approval workflows and audit trails to bulk payments and automated reconciliation, Plooto gives our customers time back and confidence that their books are accurate and up to date. Our customers range from busy entrepreneurs to finance teams and non-profits, with a strong footprint among accounting firms and bookkeeping professionals across Canada.

About the Role

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, and turning those insights into action. You will identify what we can improve now through tooling, automation, AI, or process changes, and where deeper Product or Engineering investment can create meaningful impact.

You will bring together deep customer understanding, payments expertise, hands-on data analysis, and strong business judgment to uncover root causes, quantify customer and business impact, and translate insights into clear recommendations that drive measurable improvement.

What You'll Do

• Uncover the biggest opportunities to improve the customer journey. Bring together customer contacts, churn, payment behavior, operational data, reviews, and NPS/CSAT to identify friction and the opportunities with the greatest customer and business impact.
• Diagnose what is driving the experience. Go beyond high-level themes to understand the underlying product, payment, process, policy, tooling, or integration drivers and define the outcomes that matter most.
• Shape customer experience priorities across SaaS and payments. Identify where product workflows, payment flows, and operational processes create friction and help define the customer and business outcomes that should improve.
• Turn data into decisions. Test hypotheses, segment customers, quantify impact, and connect insights to contact rate, churn, revenue retention, and cost-to-serve.
• Create momentum now while shaping what comes next. Identify opportunities through AI, automation, tooling, communications, and process improvements, while partnering with Product and Engineering on opportunities that require deeper product investment.
• Influence high-value improvements across Plooto. Use strong problem framing, evidence, and clear target outcomes to build alignment across Product, Engineering, Customer Operations, Risk, Data, Finance, and GTM.
• Build a stronger Customer Experience capability. Evolve how Plooto measures and acts on customer insights, create reliable visibility into contact and churn drivers, and translate complex analysis into concise, decision-ready recommendations for senior leaders.

What We're Looking For

• 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.

Why Become a Plootonian?

If you’re looking to make a meaningful impact, look no further. We’re transforming the payments space in North America by delivering an unrivalled product experience to solve a real and pressing problem for SMBs.

The biggest reason small businesses fail is poor financial management and cash flow — and Plooto fixes that. We have strong product-market fit, a massive opportunity ahead, and the backing of experienced fintech leaders.

You’ll join a team that cares deeply about customer impact, takes pride in our craft, and moves with urgency. We’re just getting started — and you’ll help shape the next chapter of our growth story.

Join Plooto and be part of a mission that matters.

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Our Commitment to Inclusion 

Plooto is committed to building an inclusive workplace where people of all backgrounds, experiences, and perspectives can thrive. We know great teams are built through diverse thinking, and we encourage you to apply even if your experience does not align perfectly with every qualification listed. 

Accommodation is available throughout the recruitment process in accordance with applicable accessibility legislation. If you require accommodation at any stage, please let us know—we’re happy to work with you. 

This posting is for one available position. Compensation will be determined based on the successful candidate’s knowledge, skills, experience, and overall alignment with the role.