WorkWhile is on a mission to help workers earn a better living and live better lives. More than 80 million Americans work hourly jobs — often with unpredictable schedules, near-minimum wages, and few benefits — leading to real financial instability. We're fixing that.
WorkWhile is evolving from a high-growth labor marketplace into a comprehensive workforce platform, expanding our product suite to include Newday (our SaaS workforce management system) and WorkWhile Wallet (our fintech solution for worker earnings and credit). The result is a multi-business-model company with a genuinely complex, interesting financial landscape.
Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, we're disrupting the $650 billion staffing and recruiting market.
The OpportunityThis is not a "maintain the books" Controller role. This is a build-it role.
As Corporate Controller, you'll serve as the CFO's right hand in architecting a world-class accounting function from the ground up — one capable of supporting high-volume transaction processing, multi-stream revenue recognition (Marketplace + SaaS + Fintech), and banking-level treasury operations. You'll lead an ERP migration, deploy AI-driven automation, and own the technical accounting for business models that most Controllers never get to work across simultaneously.
If you're a technically deep CPA who wants to do more than close the books — someone who wants to shape financial infrastructure at a venture-backed, mission-driven company — this role is built for you.
What You'll Own1. Core Accounting OperationsFull-cycle accounting ownership: General Ledger (GL), Payroll, Procure-to-Pay (P2P), Order-to-Cash (O2C), and Record-to-Report (R2R)
Data integrity: Partner with Data Science to ensure financial data in the ERP (NetSuite/Intacct) aligns precisely with operational data sources (BigQuery, Metabase)
High-volume payroll: Manage complex weekly and daily payroll runs for a nationally dispersed workforce, with distinct treatment for W2 employees (taxes, benefits, withholdings) and 1099 independent contractors
Month-end & year-end close: Own the close calendar, drive down close cycle times, and ensure a clean, audit-ready general ledger at all times
Revenue Recognition (ASC 606): Author technical accounting memos and policy for multiple evolving revenue streams — including "Principal vs. Agent" gross-to-net calculations for marketplace revenue and subscription revenue recognition for the Newday SaaS product
Fintech & Treasury Accounting: Build accounting workflows for WorkWhile Wallet and W2 Early Pay — including daily liquidity management for payroll funding, high-volume card transaction reconciliation (Marqeta, Stripe), and accounting for potential credit losses on worker advances
Equity & Stock-Based Compensation: Manage equity plan administration and ASC 718 accounting
Multi-jurisdiction Tax Compliance: Oversee federal, state, and local tax filings; manage payroll tax nexus across all states where W2 workers operate; address sales tax implications for SaaS products
Audit leadership: Own the external audit relationship end-to-end — prepare PBC schedules, manage fieldwork, and deliver audited financial statements on time
Investor & lender reporting: Prepare accurate, well-documented financials for board reporting, debt covenant compliance, and future fundraising due diligence
ERP migration: Lead the evaluation and implementation of a scalable ERP upgrade (e.g., QuickBooks Online → NetSuite or Sage Intacct), including integration with billing, payroll, and payments systems
AI & automation: Proactively identify and deploy AI agents for reconciliation, invoice processing, and anomaly detection — reducing manual workload and improving accuracy
Collections & DSO optimization: Strengthen billing and collections processes, managing invoicing nuances across Enterprise and SMB client segments
Team development: Manage and mentor the internal accounting team and oversee the offshore BPO team, ensuring seamless collaboration across time zones
Active CPA license — non-negotiable
Big 4 accounting firm experience: Minimum 4–6 years in audit at a Big 4 firm (Deloitte, PwC, EY, or KPMG), serving public company or high-growth technology clients
10+ years of progressive accounting experience, with at least 3 years as a Controller or Assistant Controller at a venture-backed technology company
Deep technical accounting expertise in ASC 606 revenue recognition, including multi-element arrangements and gross vs. net revenue treatment
Proven track record of ERP implementation — specifically migrating from QuickBooks to NetSuite, Sage Intacct, or equivalent
Experience managing multi-state payroll tax compliance and nexus analysis for a company with a distributed workforce
Industry experience in Marketplace, Fintech (lending, ledgering, prepaid cards), or SaaS business models
Hands-on experience with Stripe, Marqeta, or similar payment processors from an accounting and reconciliation standpoint
Experience managing hybrid onshore/offshore accounting teams or BPO relationships
Exposure to SQL, BigQuery, or BI tools (Looker, Metabase) for financial data analysis
Are the kind of person who investigates a variance until it's fully explained — not just deemed immaterial
Can translate complex accounting positions (like Gross vs. Net revenue) clearly for non-finance stakeholders, investors, and lenders
Are energized by ambiguity and want to build, not just maintain
Have a strong bias for action and take pride in operational excellence
Competitive base salary + equity in a high-growth, venture-backed company
Hybrid work culture with office hubs in SF, NY, Seattle & Toronto
In-person company off-sites
Medical, dental & vision coverage
Unlimited PTO
401(k) with employer match
WFH stipend to support your home office setup
WorkWhile has a diverse, mission-driven, and supportive culture—we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we’d love to chat!
Top Skills
WorkWhile Toronto, Ontario, CAN Office
Toronto, ON, Canada
