Director, Revenue Operations

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.

Director of Revenue Operations

We’re looking for a Director of Revenue Operations to build and scale the systems, processes, and insights that power our go-to-market engine. This role sits at the center of Sales, Marketing, Customer Success, and Finance—driving alignment, improving performance, and enabling predictable, scalable revenue growth as Plooto continues to grow.

You’ll bring structure to how we operate, clarity to how we measure success, and momentum to how we execute. You’ll also play a key role in modernizing how we work, leveraging AI and automation to make our GTM teams faster, smarter, and more effective.

What You’ll Do

• Own and optimize the end-to-end revenue engine across Marketing and Sales - from lead to close to expansion and retention
• Build and optimize a hybrid product-led and sales-supported growth model - ensuring a smooth experience between in-product conversion and rep-led or channel-driven sales where needed
• Drive forecasting, pipeline management, and reporting to improve predictability and decision-making
• Partner with GTM leaders to define targets, KPIs, and performance frameworks that align to company goals
• Build and scale revenue processes that are efficient, repeatable, and adaptable as we grow
• Improve data quality, visibility, and accessibility across the funnel to enable better insights and faster decisions
• Lead CRM (Salesforce) strategy, governance, and ongoing optimization
• Own and evolve the revenue tech stack, ensuring systems are integrated, scalable, and delivering real value
• Identify and implement automation and AI-driven solutions to increase efficiency, improve accuracy, and unlock new capabilities across GTM teams
• Support strategic planning, including annual planning, territory design, and capacity modeling
• Analyze performance trends and deliver clear, actionable recommendations to leadership
• Build and lead a high-performing RevOps function as the company scales

How You Work

• AI-native operator: You don’t just use AI, but you rethink how work gets done with it. You’ve implemented AI to automate workflows, enhance decision-making, enrich data, or unlock new insights. You can point to specific examples where AI meaningfully improved speed, quality, or revenue outcomes.
• Deeply collaborative partnerships: You approach RevOps as both a strategic and service function. You listen first, understand the real problem, and work alongside stakeholders to design the right solution. You build trust through partnership and consistently elevate the teams around you.
• Systems thinker with a bias for action: You see how tools, data, and processes connect—but you don’t over-engineer. You prioritize what matters, move quickly, and iterate as you go.

What You Bring

• 7–10+ years of experience in Revenue Operations, Sales Operations, or GTM Strategy
• Experience in a high-growth SaaS environment (fintech experience is a major plus)
• Hands-on experience owning and optimizing a modern revenue tech stack
• Proven ability to integrate systems and ensure clean, reliable data flows across the funnel
• Demonstrated experience applying AI and automation to improve GTM performance (e.g., forecasting accuracy, pipeline generation, sales productivity, customer expansion)
• Strong expertise in forecasting models, dashboards, and reporting frameworks
• Deep understanding of funnel metrics, pipeline dynamics, and revenue drivers
• Strong analytical skills, with experience using SQL, BI tools, or data platforms (preferred)
• Track record of driving cross-functional alignment and influencing senior leaders
• Experience building or scaling RevOps processes in a growing organization
• Excellent communication skills - able to translate complex data into clear, actionable business insights
• Bachelor’s degree in Business, Finance, Analytics, or a related field (MBA or relevant certifications are a plus)

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.

What We Value

• Curiosity and a drive to continuously improve how work gets done
• Ownership and accountability—you follow through and deliver results
• Thoughtful, intentional execution over unnecessary complexity
• A genuine desire to help teams succeed and perform at their best

Show Us

We care deeply about how you think and operate.

Be ready to share specific examples of how you’ve used AI to meaningfully improve a go-to-market workflow, decision, or outcome—and how you partnered with stakeholders to make it successful.

Equal Opportunity & Accessibility

We are an equal opportunity employer and are committed to building a diverse and inclusive workplace. We welcome applications from individuals of all backgrounds and experiences. Accommodations are available upon request throughout the recruitment and selection process. If you require accommodation, please contact us at HR@plooto.com.

AI in Hiring

We may use technology, including artificial intelligence, to assist in the screening, assessment, or selection of applicants. These tools are used to support fair and consistent hiring practices.

Applicant Privacy & Process

We thank all applicants for their interest; however, only those selected for further consideration will be contacted. There is one vacant role open for this position.

About Plooto

Plooto is a fast-growing Canadian fintech company on a mission to revolutionize how businesses manage payments. We help accounting firms and their clients automate and simplify payables, receivables, and workflows, saving time and unlocking growth. As a nimble start-up, we thrive on innovation, collaboration, and empowering our customers to succeed. 

The Role

We are looking for a Customer Success Manager (CSM) to join our Sales team and play a key role in onboarding accounting firms and driving the adoption of Plooto across their client base. This role blends customer success, sales, and strategic account management. Your success will be measured by how effectively you help accounting firms bring their clients onto Plooto and grow their usage over time.

This is an exciting opportunity for someone who thrives in a fast-paced start-up environment, loves building relationships, and has a hunter mentality when it comes to driving results.

What You’ll Do

• Own the onboarding journey for new accounting firm partners, ensuring smooth adoption for both firms and their clients.
• Build and maintain strong relationships with firm leaders to drive client expansion on Plooto.
• Act as a trusted advisor, educating partners on best practices and helping them unlock full value from Plooto.
• Manage a portfolio of accounts with a focus on increasing:
  • Number of clients onboarded
  • Product usage and feature adoption
  • Payment volume and overall engagement
• Carry and deliver against a new subscriber target with commission tied to client growth.
• Identify opportunities to upsell, cross-sell, and expand firm adoption.
• Collaborate with sales, product, and support teams to provide customer feedback and continuously improve the experience.

What We’re Looking For in this Sales Role:

• 3+ years of experience in customer success, account management, or sales, preferably in SaaS, fintech, or payments.
• Proven track record of meeting or exceeding new subscriber, growth, or expansion targets.
• Strong relationship-building skills with a natural curiosity to understand customer needs and challenges.
• A hunter mentality, driven to grow accounts and achieve ambitious goals.
• Excellent communication, problem-solving, and organizational skills.
• Comfort working independently in a fast-paced start-up environment.
• Bonus: experience in the accounting software or payments ecosystem.
• Must be legally eligible to work in Canada and based in Canada.

Why Join Plooto

• Be part of a Canadian fintech start-up that’s reshaping how businesses manage payments.
• Work remotely while collaborating with a passionate, high-performing team.
• Competitive salary plus commission tied to growth and success.
• Opportunity to learn, grow, and make a direct impact on the company’s trajectory.

This is a fully remote role open to candidates in BC, AB, ON, and NS. There is one open vacancy. 

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

Plooto powers payments and cash flow management for 14,000+ businesses across North America — and we’re just getting started.

We’re rebuilding and scaling the next generation of our fintech platform, and we’re looking for a Senior Backend Engineer who wants real ownership, real scale, real impact, and cares deeply about system design, scalability, and writing clean, testable code that stands the test of time.

This is not a feature-factory role.

You’ll design and build high-throughput, cloud-native systems that move money, power complex workflows, and deliver real-time financial insights. You’ll help shape architecture decisions, influence engineering standards, and raise the technical bar across the team.

If you thrive in high-growth environments, care deeply about clean system design, and enjoy solving hard distributed systems problems — you’ll feel at home here.

We move fast. We debate ideas, not egos. We hold a high bar. And we win as a team.

Key Responsibilities

What you'll do:

• Own the design and delivery of scalable backend services using .NET and Azure
• Architect and evolve event-driven, distributed systems that process high volumes of financial transactions
• Build API-first services with strong contracts, reliability, and observability
• Lead complex technical initiatives from design through production rollout
• Make pragmatic architecture decisions that balance speed, scalability, and long-term maintainability
• Partner closely with Product and Design to translate ambiguous problems into elegant technical solutions
• Improve performance, reliability, and system resilience as we scale
• Raise the engineering bar through thoughtful code reviews, design discussions, and mentorship
• Inspire and share your engineering passion across the whole engineering org in our regular Lunch & Learn sessions
• Contribute to a culture of experimentation, ownership, and continuous improvement
• Work cross-functionally in Plooto, distilling the needs of our strategy into actionable engineering output

Qualifications

Outline the experience, technical skills, and attributes required to succeed in the role. Include both must-haves and nice-to-haves if applicable.

Your background:

• 5+ years of professional backend engineering experience (preferably in high-growth or product-led environments)
• Strong expertise in C# (or another strongly typed language) and modern backend design principles
• Proven track record of writing production-grade, testable, maintainable code
• Deep experience designing and building RESTful APIs in production
• Hands-on experience with cloud-native architectures (Kubernetes, serverless, managed services), ideally in Azure
• Experience building or operating distributed, high-throughput systems
• Experience with event-driven architectures and streaming systems (Kafka or similar)
• Experience implementing automated testing strategies (unit, integration, contract, and end-to-end testing)
• Strong understanding of data storage patterns across RDBMS and NoSQL systems
• A bias toward ownership, action, and accountability
• Ability to navigate ambiguity and drive clarity in fast-moving environments
• Previous track record working successfully in a cross-functional team environment
• Ability to effectively use AI tools towards increasing velocity, efficiency and quality of deliverables
• Computer Science degree or equivalent

Bonus Points

• Experience in fintech, payments, or regulated domains
• Prior startup experience where you helped scale systems and teams

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.

There is currently one open position for this role.

As part of our recruitment process, we may use AI tools to support candidate review and selection.

We are an equal opportunity employer and welcome applications from individuals of all backgrounds. We are committed to building a diverse and inclusive workforce. While we appreciate all applications, only those selected for further consideration will be contacted. Accommodations are available throughout the recruitment and employment process. If you require accommodation, please contact us at hr@plooto.com

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

Location: Remote, India

Employment type: Employer of Record

We're looking for an Account Executive to join our SMB Sales team and help bring Plooto's all-in-one AP/AR payment platform to small and independent businesses across North America. You'll be joining a focused, driven team working through an important chapter in Plooto's growth, with meaningful work to do and real opportunities to develop as the business evolves.

You'll primarily manage a pipeline of warm inbound leads from businesses actively exploring better ways to manage their payments. When the opportunity arises, you'll also engage in targeted outbound outreach, so comfort with both motions is essential. You'll play a direct role in shaping how Plooto grows its SMB customer base.

Key Responsibilities

• Own the full sales cycle for SMB prospects, from initial discovery through close, ensuring a consultative and customer-first buying experience.
• Manage and convert a steady pipeline of inbound leads from businesses looking to automate and simplify their accounts payable and receivable processes.
• Execute outbound outreach to targeted prospect segments when needed, bringing the same disciplined, customer-first approach to every engagement.
• Conduct compelling discovery calls and product demonstrations that clearly connect Plooto's platform to each prospect's specific pain points and goals.
• Maintain disciplined CRM hygiene in Salesforce, with accurate pipeline stages, timely disposition logging, and quality deal notes that support team-wide forecasting.
• Collaborate with Revenue Operations, Product, and Marketing teams to ensure smooth handoffs and share field insights that improve how we go to market.
• Consistently meet and exceed monthly performance targets including deals closed, new subscriber numbers, and payment feature activation rates.
• Share learnings from customer conversations to help sharpen the team's messaging, talk tracks, and objection-handling playbooks.

Qualifications

Must-Have

• 3+ years of B2B SaaS or fintech sales experience with a consistent track record of quota attainment.
• Proven experience selling to small and independent businesses; you understand their buying behaviour, timelines, and decision-making dynamics.
• Comfortable running both inbound and outbound sales motions; you know how to generate momentum regardless of where a conversation starts.
• Strong discovery and qualification skills; you ask the right questions, listen actively, and tailor your pitch accordingly.
• Hands-on experience with Salesforce or a comparable CRM; you keep your pipeline clean and use data to manage your time well.
• Excellent written and verbal communication skills in English; confident on the phone and equally effective in async channels.

Nice-to-Have

• Background in payments, accounting software, or financial tools, or prior experience working with accountants and bookkeepers.
• Experience with sales engagement tools such as outreach sequencing platforms or VoIP tools like Aircall.
• Prior experience in a high-growth or fast-changing environment where you've had to adapt quickly as the playbook evolved.
• Familiarity with compliance considerations in financial software sales (e.g., CASL, TCPA).

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.