Remote Enterprise Customer Success Manager

About Plooto

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.

About the Role

We are looking for an Enterprise Customer Success Manager (CSM) to join our Sales team and own relationships with our most strategic, high-value partners. 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 opportunity 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.

Key Responsibilities

• 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.
• Identify, develop, and close upsell and cross-sell opportunities within your book of business, carrying an expansion revenue target with commission tied to growth.
• 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.
• Collaborate cross-functionally to resolve escalations quickly and maintain a high bar for enterprise client experience.
• Travel periodically to visit enterprise partner offices, strengthening relationships with key stakeholders and supporting on-site business reviews, onboarding milestones, or strategic planning sessions.

Qualifications

• 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.
• Executive presence, comfortable leading QBRs, navigating C-suite relationships, and influencing without authority.
• 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.
• A hunter mentality balanced with deep relationship instincts, knowing when to push and when to listen.
• 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.

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.

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.