Toronto
· Full-time
· In office five days a week
· $120,000–$150,000 + meaningful equity Entries is building an AI-native accounting firm for owner-operated businesses. We are looking for a Product Manager, Accountant to own exceptional client work, bring deep tax judgment, and help build the professional-services side of the company from the ground up. Entries exists to power prosperity for owner-operated businesses. Business owners should be building their companies—not closing the books, chasing receipts, worrying about filings, or trying to decode what their numbers mean. We are building the financial back office we wanted when running our own companies: responsive, proactive, and actually useful. We are a team of accountants and engineers rebuilding the accounting firm around what AI now makes possible. Agents do the repetitive work: gathering evidence, processing documents, preparing entries, surfacing exceptions, and drafting deliverables. Accountants exercise judgment, own the client relationship, set the standard, and remain accountable for the result. We automate the work. We do not automate accountability. The role

This is a founding role with an unusually broad mandate. You will be responsible for the quality of our accounting and tax work for owner-operated businesses. You will advise clients directly, review complex work, and make sure every number and filing meets a high professional standard. You will also help us build professional services at Entries: defining our service model, designing engagements, developing standards and controls, improving pricing and delivery, and turning recurring client needs into scalable workflows, tools, and agent capabilities. This is not a conventional accounting job with AI added around the edges.



We want someone who is excited to rethink how a professional-services firm should operate when accountants and engineers work side by side. What you will do

Own trusted relationships with owner-operated businesses and their founders. Lead accounting, tax compliance, tax planning, and advisory work from initial scoping through final delivery. Review financial statements, reconciliations, workpapers, tax returns, and client deliverables. Identify tax risks and planning opportunities before clients have to ask. Translate financial and tax complexity into clear, practical advice for business owners. Build the professional-services function: service lines, engagement standards, quality controls, review processes, capacity planning, pricing, and client experience. Help define what excellent service looks like and make it repeatable without making it bureaucratic. Work directly with engineers to turn recurring work, professional judgment, and firm policy into reliable agent workflows. Review agent output, improve its context and rules, and decide where human judgment must remain in the loop. Spot broken processes and help eliminate them instead of getting faster at the workaround. Protect the integrity, confidentiality, and timeliness of every client deliverable. The tax experience we are looking for

You have strong hands-on Canadian tax experience with owner-operated businesses and the people behind them.



Your experience should include many of the following: Tax filings and compliance

Preparing and reviewing T2 corporate income tax returns and supporting schedules for Canadian-controlled private corporations. Preparing or reviewing T1 personal income tax returns for founders, shareholders, and owner-managers. Preparing GST/HST returns and resolving sales-tax issues across common business activities. Preparing and reviewing T4, T4A, T5, and other information returns relevant to private companies and their owners. Managing corporate tax instalments, balances owing, elections, deadlines, and notices of assessment or reassessment. Supporting CRA reviews, audits, information requests, and correspondence. Working with common owner-managed structures, including operating companies, holding companies, partnerships, and family trusts. Coordinating year-end tax work with bookkeeping, payroll, financial statements, and the close so compliance is accurate and productive. Tax planning and advisory

Advising owner-managers on salary, dividends, bonuses, and other remuneration strategies. Planning around shareholder loans, related-party transactions, intercompany balances, and personal use of corporate assets. Helping clients manage instalments, cash flow, loss utilization, capital purchases, and capital cost allowance. Advising on holding-company structures, intercorporate dividends, and the movement of cash between related entities. Supporting incorporations, corporate reorganizations, section 85 rollovers, estate freezes, and succession planning, independently or alongside specialist counsel. Planning for the purchase or sale of a business, including share-versus-asset considerations, QSBC status, purification, and access to the lifetime ca

📌 Product Manager, Accountant (Toronto)
🏢 Tryentries
📍 Toronto