---
title: 'Enterprise Customer Success Manager at Plooto'
canonical: 'https://feeny.ai/job/enterprise-customer-success-manager-plooto-toronto-ontario-canada-fjraqh0ba9aq'
type: 'job'
last_seen: '2026-09-08'
---

# Enterprise Customer Success Manager at Plooto

- **Company:** Plooto
- **Location:** Toronto Ontario Canada, India
- **Posted:** 2026-09-08
- **Last confirmed live:** 2026-09-08
- **Apply:** https://job-boards.greenhouse.io/plootocareers/jobs/5417764008

## Job description

## 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.

## About Plooto

## Company Overview
- **One-liner**: Plooto is an all-in-one payment automation platform that helps small and midsize businesses and their accountants streamline accounts payable and receivable in one secure, easy-to-use solution.
- **Entity Type**: Private (Series B)
- **Headquarters**: Toronto, Ontario, Canada
- **Founded**: 2015
- **Founders**: Serguei Kloubkov (Co-Founder & Co-CEO), John McLane (CEO)

## Core Business
- **Primary industry/industries**: Financial Services, Fintech, Payment Automation
- **Target customers**: Small and Midsize Businesses (SMBs), Accounting Firms, Bookkeepers
- **Mission or purpose statement**: To put businesses in control of their finances so they can build the future of their dreams.

## Products & Services
- **Accounts Payable (AP) Automation**: Automates the entire bill payment process, from invoice receipt to approval and payment execution. Includes custom approval workflows, two-way sync with accounting software (QuickBooks, Xero, NetSuite), and real-time payment tracking.
- **Accounts Receivable (AR) Automation**: Automates the invoicing and collections process, sending invoices, collecting payments, and syncing back to accounting software for full cash flow visibility.
- **International Payments**: Facilitates cross-border payments with competitive exchange rates, clear fees, and built-in compliance for paying international vendors.
- **Payment Options**: Supports EFT/ACH, credit card, foreign exchange, and instant payments via a pre-funded Plooto Instant account.
- **Accounting Software Integration**: Two-way sync with QuickBooks, Xero, and NetSuite for seamless reconciliation and data entry reduction.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed
- **Key Metric**: Annual Revenue of $35.0M (USD) and Total Funding of $29.4M (USD)
- **Notable Investors/Partners**: Centana Growth Partners (led Series B), FINTOP Capital (led Series A). Key integrations with QuickBooks, Xero, and NetSuite.
- **Growth Signals**: Supports 14,000+ businesses, processes 3.2M+ transactions annually, has grown headcount 5.6% year-over-year to 81 employees, and has a presence in Canada, the United States, India, and the United Kingdom.

## Competitive Advantages
- **Deep Accounting Integration**: Two-way sync with QuickBooks, Xero, and NetSuite creates a sticky ecosystem for accounting firms and their clients, reducing manual data entry and errors.
- **Unified AP & AR Platform**: Combines both accounts payable and receivable in a single platform, offering a complete cash flow management solution that competitors often split into separate tools.
- **Customizable Approval Workflows**: Provides granular control over payment approvals, reducing firm risk and ensuring compliance, which is a critical need for accounting firms.
- **Built-in Compliance for International Payments**: Simplifies complex cross-border payments with transparent fees and regulatory compliance, a key pain point for SMBs.

## Strategic Focus
- **Deepening Accounting Ecosystem**: Continuing to strengthen integrations with major accounting platforms (QuickBooks, Xero, NetSuite) to become the default payment layer for accounting firms.
- **Product Expansion**: Building out a more complete cash flow management platform that unifies payments, processes, control, reconciliation, and reporting.
- **Scaling Customer Base**: Growing beyond 14,000 businesses by expanding sales and marketing efforts, particularly in the US and international markets.
- **International Growth**: Expanding presence in the United States, India, and the United Kingdom to capture a larger share of the global SMB payment market.

## Why Work Here
- **Meaningful Impact**: Employees directly shape how thousands of businesses run and grow, with a clear mission to empower SMBs.
- **Growth Opportunities**: The company invests in learning and development, and the fast-growing fintech environment offers career advancement.
- **Inclusive Culture**: Celebrated diverse perspectives, with 86% of employees rating it a great place to work (vs. 60% at a typical company) according to Great Place to Work® Canada.
- **Flexibility and Balance**: Supports hybrid and remote-friendly ways of working, with many roles listed as "Remote - Canada" or "Remote - India."
- **Forward Momentum**: Part of a fast-growing fintech that is constantly evolving, with a clear product roadmap and international expansion.
- **Engineering Culture**: The engineering team is a core part of the business, with a Senior Backend Engineer role currently open. The company values data-informed learning and taking smart risks.
- **Hiring Process**: A structured 4-step process: Screening interview → Take-home or on-call case study → Final interview → Reference & background checks → Offer.

## Sources
1. [plooto.com](https://www.plooto.com/)
2. [plooto.com/careers](https://www.plooto.com/careers)
3. [job-boards.greenhouse.io](http://job-boards.greenhouse.io/plootocareers)
4. [greatplacetowork.ca](https://www.greatplacetowork.ca/en/certified-company/z4870188000002257001)
5. [linkedin.com](https://ca.linkedin.com/company/plooto)

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