Order-to-Cash Lead

Lovable•New York, NY

10h

About The Position

Lead Lovable’s Order-to-Cash function, connecting enterprise sales with billing, collections and Revenue Accounting, while reconciling cash across sales-led and product-led revenue. The role ensures that commercial agreements become accurate billing and complete records, and builds an AI-first function in which invoicing, cash application, collections follow-up and reconciliations are automated or agent-driven where possible. The position partners with Deal Desk and go-to-market teams on enterprise deals, renewals, expansions and amendments; owns enterprise billing, collections, cash application and partner payouts; maintains complete contract and customer records; and reconciles marketplace and payment-processor activity to the ledger. It also supports Revenue Accounting and external audits with timely, complete records, reconciliations and evidence. The Order-to-Cash Lead designs and builds AI-first workflows and helps develop the broader quote-to-cash process with Deal Desk, RevOps and Financial Systems. The role is suited to someone who has operated in a rapidly scaling business and prefers building processes and solutions over maintaining an established function. Revenue Accounting retains responsibility for accounting conclusions and significant judgements, while Billing Engineering owns product-led billing logic.

Requirements

At least 8 years of experience in billing, collections, quote-to-cash, deal desk or Finance revenue operations.
Hands-on enterprise SaaS experience and experience leading a process end to end.
Experience working in a rapidly scaling business, with specific examples of billing and collections problems encountered and how they were resolved.
Hands-on use of AI or automation to change an order-to-cash process, and strong views on what an AI-first function should look like.
Ability to read commercial agreements and translate subscription and usage-based terms, including commitments, overages, credits and contract changes, into billing schedules, entitlements and operational requirements.
Working knowledge of revenue recognition and ability to identify terms that require accounting assessment.
Experience with collections, cash application and high-volume payment processor or app store reconciliation.
Strong spreadsheet, reconciliation and systems-investigation skills.
CRM and billing-platform experience.
Clear communication skills and sound judgement to challenge incomplete requests while helping colleagues find workable solutions.
A record of improving processes while maintaining reliable daily operations.
Comfort building solutions and workflows, using AI tools regularly and treating AI as a default way of working.

Nice To Haves

SQL experience.
Workflow automation experience.
Experience building your own tools with AI.

Responsibilities

Partner with Deal Desk and GTM on enterprise deals, renewals, expansions and amendments, shaping workable options for non-standard requests and explaining their billing, cash-flow and operational implications.
Resolve standard commercial and billing matters within agreed authority, and escalate exceptions with supporting facts, options and a recommendation; flag matters requiring Revenue Accounting, Tax or Legal input.
Contribute operational and accounting considerations to pricing and packaging decisions before commitments are made.
Manage enterprise billing setup, billing schedules, invoice preparation and issuance, and approved corrections and credit notes.
Ensure billing details, purchase orders, tax information and invoice timing reflect agreed terms, and reconcile contracted terms with provisioned entitlements and invoices.
Resolve billing queries and payment blockers with Sales, Customer Success and customer finance teams.
Own collections, accounts receivable aging and DSO, automating follow-up where possible; own cash application, keep unapplied cash close to zero, and prepare inputs for the allowance for credit losses.
Calculate, validate and issue partner payouts on schedule; reconcile payouts against partner agreements, resolve queries and document billing and reconciliation processes for partner marketplace arrangements.
Own Finance intake for agreements and changes, including amendments, renewals, cancellations, concessions and migrations; maintain executed documents, effective dates, approvals and clear records of changes.
Maintain links among contracts, customers, billing accounts and workspaces across HubSpot, Lovable’s internal billing platform and Light; resolve missing records and mismatches with responsible teams.
Reconcile marketplace and payment-processor activity, including payouts, fees, refunds and chargebacks, to the ledger and usage and billing data.
Provide Revenue Accounting with complete commercial-event and billing records on an agreed timetable, including supporting reconciliations and explanations of exceptions.
Prepare evidence and schedules in line with established accounting requirements, escalate matters requiring judgement, maintain operational procedures and evidence of checks, and support external order-to-cash audits.
Design and build AI-first workflows for invoicing, cash application, collections follow-up and reconciliations.
Work with Deal Desk, RevOps and Financial Systems to design an AI-first quote-to-cash process, owning the billing-to-cash portion.
Resolve recurring issues directly where possible; otherwise, define clear requirements for Financial Systems, Billing Engineering and Data, create test cases from customer scenarios, conduct business testing and verify fixes.
Handle routine exceptions and operational investigations while coordinating with Revenue Accounting, which retains responsibility for recognition, allocation, significant judgements, estimates and close conclusions.
Reconcile product-led billing outputs to cash and the ledger, working alongside Billing Engineering, which owns product-led billing logic.