Billing, Collections & Deal Support Specialist

Overview

Macabacus is looking for a detail-oriented and hands-on Billing, Collections & Deal Support Specialist to join our growing team and help scale our end-to-end billing and collections operations. This role is being added due to company growth and increasing operational needs, and will work closely alongside another team member currently supporting these functions. In this hybrid role, you will support billing, collections, post-sale deal support, sales operations, tax compliance, and process improvement initiatives across the organization. You will be responsible for ensuring billing accuracy, managing cash collections, reconciling sales tax and VAT payable accounts, improving AR performance, and helping optimize a scalable quote-to-cash process. This role requires someone who is comfortable wearing multiple hats, working cross-functionally, and identifying opportunities to improve systems and processes. The ideal candidate thrives in a fast-paced SaaS subscription environment, is highly collaborative, and is excited to leverage new AI tools and automation opportunities to improve efficiency.

Key Responsibilities

Billing & Invoicing Manage the daily and monthly invoicing lifecycle in Recurly, including subscriptions, usage based, proration, and billing rules Ensure accurate and timely invoice generation and delivery for recurring, usage-based, and manual billing Maintain billing schedules, monitor payment retries, and oversee dunning workflows to reduce failed payments Maintain customer portals for invoice submission and billing communication Cash Collections & AR Oversight Own the cash collection process, proactively managing aging accounts and customer outreach to drive timely payments Prepare and maintain weekly AR aging reports; identify high-risk accounts and escalate as needed Collaborate with Sales and Sales Operations to resolve disputes, review open balances, and align on customer communication strategies Reconcile accounts receivable balances and billing records across systems Deal Support & Sales Operations Provide post-sale deal support by reviewing completed deals for accuracy, compliance, and proper documentation Support sales operations with pricing validation, quoting support, contract alignment, and customer account setup Assist with maintaining accurate customer, billing, and reporting data within CRM system Tax Compliance Reconcile all sales tax and VAT payable accounts and coordinate with external partners to ensure compliance Administer and maintain sales tax configurations using Avalara AvaTax or similar tax automation platforms Accounting & Reporting Reconcile data flows between billing systems and accounting platforms such as QuickBooks/Salesforce/Recurly/Stripe Support monthly close activities with billing-related entries, reconciliations, and reporting Ensure accurate deferred revenue tracking and revenue recognition consistent with ASC 606 Provide billing documentation and schedules for internal and external audits Process Improvement & Cross-Functional Support Continuously optimize billing, collections, and AR workflows through automation, AI, and process improvements Partner with Sales, Customer Success, Finance, Operations, and Product teams to support seamless quote-to-cash execution Maintain and update SOPs and assist with training team members on systems and processes Evaluate and adopt new AI tools and technologies to improve operational efficiency

Required Qualifications

Advanced proficiency in Excel, including pivot tables, VLOOKUPs, and INDEX/MATCH, with the ability to manage and analyze large datasets efficiently Experience working in both B2B and B2C business environments, particularly usage based billing Experience with system implementations and billing system migration project Experience working with Salesforce (HubSpot experience is also acceptable) Hands-on experience with subscription and usage based billing platforms (Recurly/Stripe preferred; SaaSOptics, Ordway, Chargebee, or Chargify also acceptable) Experience with Avalara AvaTax or similar tax automation platforms Apply To This Job