Controller

The Role

We’re looking for a hands-on Controller to own the financial backbone of PushPress.

We’re a Series B SaaS company navigating increasing financial complexity: traditional SaaS subscriptions, AI-driven usage-based revenue, a multi-layered payments business processing nearly $1B annually, and expansion into new geographies. Our revenue model spans subscription billing, platform payment economics, and emerging AI monetization, each with distinct recognition and compliance considerations.

As our first Controller, you’ll build on the foundational work the team has already laid out. You’ll have direct insight into company strategy to ensure you have the full context that goes into setting up our accounting infrastructure for the next phase of growth. While you’ll set the direction and own the process, you’ll also be in the details: closing the books, working through nuanced recognition questions, managing the order-to-cash flow, advising on product economics from a financial lens, owning cash flow forecasting, and rolling up your sleeves to get the job done.

What You'll Own

Financial Close & Reporting

• Own the monthly, quarterly, and annual close process end-to-end with speed, accuracy, and clear documentation
• Prepare and review financial statements, reconciliations, and supporting schedules
• Build and maintain internal controls that scale with the business and hold up under audit scrutiny
• Establish the reporting infrastructure that gives leadership and the board clear, reliable visibility into company financials
• Own vendor COGS tracking and margin analysis across product lines, ensuring cost structures are well-understood as the business scales

Revenue Recognition

• Lead the application of ASC 606 across subscription SaaS, AI usage-based revenue, and platform payment revenue streams
• Ensure the accounting treatment for payments economics is clean and defensible
• Partner with GTM, Product, and Engineering to ensure billing architecture and revenue data support clean recognition
• Own the full order-to-cash flow end-to-end, including how subscriptions and payments are created in Stripe, how invoices map to revenue, how settlements land, how refunds and disputes flow back, and how it all reconciles to the GL
• Stay ahead of how our revenue model evolves (new AI features, new pricing structures, new markets) and flag accounting implications early

Cash Flow & Debt Facility

• Own cash flow forecasting and management, giving leadership real, actionable visibility into liquidity
• Manage compliance with our debt facility, including covenant tracking, lender reporting, and maintaining a healthy lender relationship
• Partner with the leadership team on capital deployment decisions and ensure strategic use of the debt facility

Tax & Compliance

• Own multi-state income tax compliance and stay current across all jurisdictions
• Lead SaaS taxability analysis and indirect tax obligations (sales/use tax) across states with nexus exposure, ensuring the company is correctly collecting and remitting where required
• Build the accounting and systems foundation to support international expansion, including GST, HST, VAT, and other indirect tax regimes as we enter new markets
• Own FX exposure tracking and multi-currency considerations as international revenue grows
• Stay ahead of new tax and compliance obligations as the business scales and new products launch

Operations & Infrastructure

• Coordinate payroll, equity/options processing, billing, AR, AP, and cash management operations, ensuring accuracy and compliance
• Evaluate and improve the accounting tech stack to support the complexity and scale ahead
• Partner with data and engineering to ensure financial data flows are reliable, reconciled, and audit-ready; comfort working with or directing modern data infrastructure (Snowflake, dbt, Stripe) is a plus
• Drive automation where it creates real leverage and accuracy; identify where manual processes are creating risk

What We're Looking For

• 8+ years of progressive accounting experience, with meaningful ownership of the close, revenue recognition, and financial reporting
• CPA required
• Deep, working knowledge of ASC 606 applied to SaaS including subscription billing, usage-based models, and multi-element arrangements
• Strong understanding of the full order-to-cash lifecycle in a Stripe-based billing environment
• Experience managing or coordinating a debt facility, including covenant compliance and lender reporting
• Multi-state tax compliance experience, including SaaS taxability and indirect tax; comfortable building out international tax capabilities as the business grows
• Comfortable utilizing AI to automate workflows and create leverage and can speak to tangible process improvements
• Have navigated ERP transitions (QBO, Rillet, Campfire, NetSuite, or similar)
• High attention to detail paired with the ability to communicate clearly to non-finance stakeholders
• Comfortable operating in a fast-moving environment where priorities shift and ambiguity is the norm

Nice to Have

• Big 4 or public accounting background
• Experience at a B2B SaaS startup, ideally with SMB customers
• Exposure to payments, fintech, platform economics, or consumption/usage-based billing models
• Experience with multi-currency reporting, FX management, or international entity structures
• Prior experience building an accounting function from scratch or significantly restructuring one
• Familiarity with AI-driven revenue models and the recognition complexity they introduce
• Comfort with modern data stacks (Snowflake, dbt, Metabase) and financial data pipeline concepts
• Experience with Ramp, Bill.com, or similar modern finance infrastructure

Benefits & Perks

• Equity Incentive Plan
• Flexible Paid Time Off (and Public Holidays)
• Health Care Plan (Medical, Dental & Vision)
• Retirement Plan (Company Sponsored 401k with Match)
• Life Insurance
• Family Leave (Maternity, Paternity)
• Work From Home Stipend
• Wellness Stipend