Plooto is a Canada-born fintech company on a mission to give small and mid-sized businesses the financial power to succeed on their own terms. We make payments secure, accurate, and stress-free so businesses and their accountants can spend less time in the books, confidently manage cash flow, and make smarter decisions every day. We’re a team that builds with integrity, agility, and heart, and we’re looking for customer-minded pros who share our passion to join us as we scale.

Enterprise Customer Success

Manager (CSM) This role is focused on managing a portfolio of large accounting firms and enterprise clients, driving deep adoption of Plooto across their client base, and unlocking significant expansion opportunities. This is a senior, high-impact role that blends executive relationship management, strategic account planning, and consultative selling. Your success will be measured by net revenue retention, expansion within your book, and the long-term health of Plooto’s most important accounts.

This is an exciting chance for a proven CSM who thrives in complex, multi-stakeholder environments and knows how to turn strategic partners into Plooto champions. This is a fully remote role open to candidates in Canada and India. Own a portfolio of enterprise and national accounting firm partners, serving as their primary point of contact and trusted advisor at the executive level.

Develop and execute tailored success plans for each account, aligned to their business goals and Plooto’s growth objectives. Drive deep adoption across firm leadership and their client base, helping partners maximize payment volume, feature utilization, and overall platform value. Lead executive business reviews (QBRs), presenting ROI, strategic roadmaps, and expansion opportunities to senior stakeholders.

Manage complex onboarding and implementation processes for large firms, coordinating internally with sales, product, support, and finance.



Act as the voice of the enterprise customer internally, surfacing feedback that shapes product prioritization and go-to-market strategy. Proactively identify risk signals and develop mitigation plans to protect and grow net revenue retention.

Travel periodically to visit enterprise partner offices, strengthening relationships with key stakeholders and supporting in office business reviews, onboarding milestones, or strategic planning sessions. 6+ years of experience in customer success, strategic account management, or enterprise sales, preferably in SaaS, fintech, or payments. Proven track record managing enterprise or national accounts with complex stakeholder maps and six-figure+ contract values. Demonstrated ability to meet or exceed NRR, expansion, or growth targets in a quota-carrying CSM or account management role.

Strong strategic thinking: able to build account plans, identify growth levers, and connect Plooto’s value to a firm’s business outcomes. Exceptional communication, organizational, and project management skills; able to manage multiple complex accounts simultaneously. Comfort operating independently in a fast-paced start-up environment where you’ll help define enterprise playbooks, not just follow them.

Bonus: experience in the accounting software, payments, or AP/AR ecosystem. The biggest reason small businesses fail is poor financial management and cash flow — and Plooto fixes that. 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. Our Commitment to Inclusion Plooto is committed to building an inclusive workplace where people of all backgrounds, experiences, and perspectives can thrive. 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.

📌 Remote Enterprise Customer Success Manager (Ontario)
🏢 Bilinguallink
📍 Ontario