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. 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. You will be responsible for the quality of our accounting and tax work for owner-operated businesses.

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. 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.

Spot broken processes and help eliminate them instead of getting faster at the workaround.



The tax experience we are looking for You have strong hands-on Canadian tax experience with owner-operated businesses and the people behind them. 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. Coordinating year-end tax work with bookkeeping, payroll, financial statements, and the close so compliance is accurate and efficient.

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.

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 capital gains exemption.



Identifying when a client needs deeper specialty advice and coordinating effectively with tax lawyers and other specialists.

Turning tax planning into clear actions clients can understand and execute—not just a memo delivered after the deadline. You do not need to have encountered every possible tax issue. Significant accounting and tax experience serving owner-operated businesses.

Strong technical judgment across Canadian corporate and owner-manager tax matters. Comfort operating with ambiguity and building systems where none yet exist. The ability and willingness to work full-time from our Toronto office, five days a week.

You have worked in a small or mid-sized public accounting firm serving private companies and their owners. You have helped build or improve a service line, firm process, quality-control system, or client-delivery model. You want to do more client work, judgment, and firm-building—and less manual production.

You can move comfortably between a client conversation, a technical tax question, a review note, and a product discussion with an engineer. You care about building a durable professional firm, not just assembling a portfolio of engagements. We want you spending as much time as possible understanding clients, spotting issues, giving advice, and setting standards—not moving information between systems.

Accountants help build the product We give people context and a clear quality bar, then expect them to make decisions and own outcomes. This role is full-time in our Toronto office, five days a week. We are building a company where an accounting issue can become a product improvement through a ten-minute conversation between the accountant who found it and the engineer who can fix it.

Meaningful equity in Entries. Unlimited AI spend for the tools that help you think, build, and deliver excellent work. The prospect to help build an entirely new kind of accounting firm from an early stage.

We will explain equity and incentives plainly, including what they mean, how they vest, what they reward, and where the risk lies.

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