Product Manager, Accountant

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 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.
• 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 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. You do need strong fundamentals, sound judgment, and the ability to know what you know, recognize what you do not, and get to the right answer.

What we are looking for

Required

• Significant accounting and tax experience serving owner-operated businesses.
• Strong technical judgment across Canadian corporate and owner-manager tax matters.
• Experience owning client relationships and explaining complex issues clearly.
• High standards for accuracy, documentation, responsiveness, and professional integrity.
• Comfort operating with ambiguity and building systems where none yet exist.
• Genuine interest in using AI as leverage while remaining accountable for the work.
• The ability and willingness to work full-time from our Toronto office, five days a week.

You may be especially well suited if

• 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 are slightly jaded by billable hours, repetitive compliance work, document chasing, and month-end heroics caused by systems nobody fixed.
• 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.

How we work

Accountants are client-facing

The most valuable part of an accountant is judgment. 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

Every repeated question, review note, unusual transaction, and broken workflow can teach our agents how to do better. Engineers write the code, but accountants provide the professional context and remain responsible for the result.

We prefer judgment to process

Process should make good judgment easier, not replace it. We give people context and a clear quality bar, then expect them to make decisions and own outcomes.

We do not bill by the hour

Clients want work done quickly, correctly, and for a predictable price. Your job is not to accumulate hours. It is to create the best outcome with the least unnecessary work.

We work together in person

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.

• Base salary of $120,000–$150,000, depending on experience and scope.
• Meaningful equity in Entries.
• Unlimited AI spend for the tools that help you think, build, and deliver excellent work.
• Direct access to engineering and the opportunity to shape our internal agentic operating system.
• Significant ownership over clients, professional standards, services, systems, and decisions.
• The opportunity 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. We will not use the promise of future upside as an excuse to underpay people today.