About Readymode

Readymode is an enterprise-grade, cloud-based, all-in-one sales engagement platform for high-volume teams - operating through a Canadian parent and two US subsidiaries. We intelligently connect sales reps with more leads in less time, maximizing productivity. We are on a mission to “transform the way businesses communicate with their customers.”

At Readymode, we live and breathe our Core Values:

We Get Stuff Done
We Strive For Mastery
We Engage In Spirited Teamwork
We Are Resilient

We embody these at all times, whether that relates to our clients or teammates. Readymode is the place to be if you like to win and value a collaborative environment that will foster your growth.

Position Summary

We are seeking a Revenue & Billing Manager to join our Finance department to help us enhance and streamline our billing processes using Maxio Advanced Billing, reconcile orders to cash, and implement the system to bill provincial, state and federal taxes correctly. This full-time, permanent position will report into our Controller, and will have 2 Billing Specialists as direct reports. This role is perfect for someone with an Accounting background, who is detail-oriented, able to effectively interpret Finance issues to cross-functional colleagues, and comfortable building their own processes.

As a Revenue & Billing Manager, you will own order-to-cash end-to-end, including billing operations performed by a two-person Billing team, monitoring accounts receivable and collections, owning the revenue and deferred revenue subledgers, and managing the compliance, sales tax and surcharge processes and reporting for both Canada and US. You will support the Billing function as it transitions back into Finance, and as the company migrates to Maxio Advanced Billing and Maxio Core. As well as a future implementation of Avalara tax engine, contemplated for late 2026/early 2027.

Location: Remote anywhere in Canada

Compensation: $90,000 - $110,000 CAD

Key Responsibilities

Billing Operations

Own the end-to-end billing cycle, including invoice runs, exception handling, and ad-hoc invoicing.
Lead and develop two Billing Specialists as the function transitions from Support & Implementation back into Finance.
Ensure billing accuracy from contract to invoice, including new customer setup, change orders, upgrades, downgrades, and cancellations.
Own the credit memo and billing adjustment process, including the development of an approval framework.
Build and maintain billing process documentation and SOPs.
Establish a recurring billing data integrity review to identify and close revenue leakage between what is contracted, provisioned, and invoiced.
Manage the chargeback dispute process with our payment processing and merchant account vendors.
Reconcile paid invoices to payment processor receipt to bank statements.

Accounts Receivable & Collections

Build a systematic collections function, including outreach cadence, escalation paths, and customer credit terms.
Own dunning and failed payment recovery. The majority of revenue is collected by credit card, making this the primary cash collection mechanism.
Perform the monthly AR-to-cash reconciliation, a control that needs redesign with Maxio.
Own cash application, AR aging, DSO reporting, and the bad debt provision analysis in conjunction with the Controller.

Revenue Accounting

Own the revenue and deferred revenue subledgers and prepare the related journal entries for Controller review.
Perform the monthly revenue subledger to general ledger reconciliation and the deferred revenue to billing system reconciliation.
Take ownership of the monthly revenue calculation, currently maintained in Excel, and transition it into Maxio Core.
Apply revenue recognition policy under ASPE and IFRS, with US GAAP readiness in view, escalating judgment calls to the Controller.
Support the annual KPMG audit on all revenue, deferred revenue, and AR areas.

Tax & Regulatory Compliance

Own go-forward US sales tax and telecom surcharge determination, billing, and remittance, including FCC Form 499, USF, state PUC, and 911 surcharges.
Reconcile surcharges billed to customers against amounts remitted, a control gap with direct margin impact.
Partner with the Controller and Avalara's implementation consultant to configure Avalara for Communications in early 2027, and own the configuration thereafter.
Monitor nexus and manage new state registrations as the customer footprint changes.

Systems & Processes

Serve as the business owner of Maxio Advanced Billing and Maxio Core following migration.
Contribute to the integration and data mapping between Maxio, the general ledger, Avalara, and downstream reporting.
Partner with the Support, Implementation, and Customer Success teams on the billing-adjacent workflows that sit outside Finance.

Qualifications and Experience

Required

5-7 or more years of progressive experience across billing operations, revenue accounting, or order-to-cash leadership.
Direct experience owning revenue recognition and deferred revenue in a subscription or recurring revenue business.
Hands-on experience implementing or administering a subscription billing platform such as Maxio, Stripe, Chargebee, Zuora, Recurly, or similar.
Demonstrated experience building an AR and collections function, not simply operating one that already exists.
Experience managing at least one direct report.
Strong reconciliation discipline and comfort owning a control from design through to evidence for auditors.
Advanced Excel, and the judgment to know when a process should leave Excel.

Strongly Preferred

US sales tax or telecom and communications tax experience, particularly exposure to a tax engine implementation such as Avalara for Communications.
Experience in telecom, communications, or a usage-based billing environment.
Exposure to a multi-entity, multi-currency structure with US and Canadian operations.
Experience supporting a Big Four audit.
CPA designation, or equivalent depth acquired through experience.

The Perks and Benefits

The tools you need to get the job done - company computer sent to you
Amazon Business Account for your WFH set up
Group RRSP matching
A full benefits package that starts on day one
Opportunity to participate in our Employee Stock Option Plan
An education and training grant in your second year
Remote and Flexible Work Opportunity

Interview Process

Screening call with People & Culture Business Partner.
Second interview with our Controller.
Final interview with our CFO.
Job offers are contingent on references.

Readymode

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