Senior Accountant (Contract-to-Hire)

About Us Gumloop is the piece of AI infrastructure companies roll out to let everyone build agents securely. Let people who understand the problem build and share agents, manage their access to data, choose your AI models and host it all in your own cloud. We're a very small team building as fast as humanly possible. Gusto, Ramp, Shopify, Samsara, Instacart, and Opendoor are running agents on Gumloop across their company. We've raised over $70M from Benchmark, First Round Capital, Y Combinator, Nexus Ventures to scale operations and are looking for people who care as much as we do to join the team. ROLE OVERVIEW As a Senior Accountant at Gumloop, you will own the in-house accounting function as we transition away from outsourced bookkeeping and build a scalable financial foundation for a fast-growing, usage-based AI platform. You will own the full close for our U.S. and Canadian entities, produce accurate financial statements in accordance with U.S. GAAP, and bring structure to revenue recognition, multi-entity consolidations, and financial controls. This role sits at the center of how Gumloop understands its unit economics. You will partner closely with leadership on revenue accounting under ASC 606—including subscriptions, usage, credits, overages, and enterprise contracts—as well as infrastructure-related COGS and the metrics that matter for a usage-based SaaS business. You will have a high degree of ownership in a lean environment, with broad scope across close, revenue, tax coordination, and process design. You will also have visibility into board reporting and our systems stack, including QuickBooks Online, Ramp, Rippling, Google Sheets, and, ideally, Stripe Billing and Stripe Revenue Recognition. ENGAGEMENT STRUCTURE This role will begin as a one year contract engagement averaging approximately 20 hours per week. The workload is cyclical, with most work concentrated around month-end and the beginning of each month. Outside of close periods, the schedule will generally be lighter and more flexible. As Gumloop’s accounting needs grow, there is an anticipated path to full-time employment. The timing of any conversion will depend on business needs, sustained workload, performance, and mutual fit. The contractor must be reliably available during agreed-upon close periods. They may support other noncompeting clients, provided those engagements do not create a conflict of interest or interfere with their commitments to Gumloop. The anticipated contract rate is $45–$65 per hour, depending on experience and qualifications. WHAT YOU’LL DO - Own the monthly, quarterly, and annual close processes for our U.S. and Canadian entities. - Prepare accurate and timely financial statements in accordance with U.S. GAAP. - Own account reconciliations, journal entries, accruals, intercompany transactions, consolidations, and financial reporting. - Manage accounts payable, payroll accounting, expense accounting, fixed assets, and cash reconciliations. - Own revenue accounting and ASC 606 revenue recognition for subscription, usage-based, and enterprise contracts. - Coordinate U.S. and Canadian corporate tax filings, sales taxes, payroll taxes, and other regulatory requirements. - Lead the accounting handoff from Gumloop’s current outsourced provider. - Strengthen accounting processes, documentation, and financial controls as the company grows. WHAT YOU BRING - Strong knowledge of U.S. GAAP and 4–5 years of accounting experience. - Experience owning the full month-end close process from start to finish. - Multi-entity accounting experience, including intercompany transactions and consolidations. - Hands-on experience with ASC 606 and SaaS revenue recognition, including subscriptions, usage-based revenue, deferred revenue, and contract assets. - A CPA or equivalent accounting qualification. - A startup ownership mindset and the ability to work independently in a fast-moving environment. - Experience with accounting and finance systems such as QuickBooks Online, Ramp, Rippling, and Google Sheets. BONUS - Experience supporting multi-entity or cross-border tax compliance and working with external advisors; prior U.S.–Canada experience is a plus. - Experience at a usage-based SaaS, AI, or developer-tools company. - Familiarity with AI infrastructure costs, including cloud hosting, model inference, and consumption-based COGS. - Experience with Stripe Billing and Stripe Revenue Recognition. - Experience supporting audits and board reporting. - Experience transitioning accounting from an outsourced provider to an internal function.