Company Description

Workleap is a Montreal-based tech company on a mission to make work simpler.

Since 2006, we’ve been building game-changing products that tackle HR and IT’s biggest challenges.

Workleap operates two distinct product lines:

The Workleap Platform, an AI-powered HR solution designed to drive team performance and boost employee engagement.
ShareGate, the leading Microsoft 365 migration and governance solution, trusted by IT professionals worldwide for its unmatched simplicity.

Today, more than 20,000 companies rely on Workleap products to grow, lead, and operate with confidence.

We’re builders at heart, with a clear purpose: to craft the simplest products that deliver exceptional value for our customers. Period.

Job Description

So, what will your new role look like?

We’re looking for a detail-oriented and collaborative Billing and Cash Application Specialist to join our revenue accounting team.

Sitting at the intersection of finance, sales, and customer operations, this role ensures seamless billing, efficient cash application, and smooth customer onboarding. Your work will directly impact revenue accuracy, cash flow, and the overall customer experience—making you an essential part of our SaaS operations.

In this fast-paced environment, your focus on accuracy, responsiveness, and process alignment will be key to supporting our continued growth.

Responsibilities

Prepare, review, and issue customer invoices according to contract terms and revenue recognition rules;
Collaborate with Sales and RevOps to ensure accurate billing for new deals, renewals, and credits;
Address customer billing and payment inquiries with professionalism and care;
Accurately apply incoming payments (ACH, wire, credit card, check) and resolve discrepancies;
Manage onboarding admin tasks like vendor forms, portal setup, and PO tracking;
Coordinate with customer procurement/AP teams to complete onboarding efficiently;
Maintain ERP and CRM data integrity and ensure audit-ready documentation;
Support internal compliance with accounting policies and tax regulations.

A typical week?  

You’ll spend your week managing the full billing and cash application cycle, from issuing accurate invoices to applying payments and resolving variances. You’ll work closely with Sales and RevOps to support new contracts, renewals, and credits, and collaborate with customers and their procurement teams to complete onboarding requirements. Along the way, you’ll keep ERP and CRM data up to date, maintain audit-ready documentation, and contribute to improving processes as the business scales. Every week combines precision, cross-team collaboration, and customer-facing problem-solving.

What does your future team look like?  

You’ll be part of the Finance team, specifically the revenue accounting function. You’ll work closely with Sales, Customer Success, and RevOps to align processes and ensure a smooth customer journey from deal closure to payment.

What are the next challenges awaiting your team?

As we scale, the team is focused on streamlining billing and onboarding workflows, strengthening internal controls, and improving automation. Having recently refreshed our order-to-cash tech stack, we are building faster, more predictable revenue cycles. You’ll play a key role in driving these improvements while ensuring excellent customer support.  

Qualifications

2-5 years of experience in billing, AR, or sales admin in a SaaS environment;
Strong attention to detail and ability to manage multiple priorities;
Experience with accounting systems (NetSuite) and Excel;
Experience with cash processing systems Recurly and Stripe
Tech savvy in the use of CRM tools like Hubspot and procurement portals;
Proactive mindset with strong communication and collaboration skills.
Ability to work on-site in Montréal once per week, including coming into the office to complete time-sensitive administrative tasks such as cheque deposits.

Salary range: $60–70k CAD.
This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate’s region to align with local market conditions.