Founding Product Designer

Tryentries; Toronto; Hybrid; CAD 100,000 - 120,000; Full time

Benefits offered by this job

Equity

AI budget

Product ownership

Direct engineering access

Job summary

Entries is seeking a founding product designer in Toronto to own the entire Entries experience and ship designs into production. You will work with founders, engineers, and accountants to redefine how a professional-services firm feels when accountants and designers collaborate with AI-enabled workflows.

You will craft the design language, build a scalable design system, and own decisions from exploration to live product.

Qualifications

• Strong hands-on product design experience shipping complex software that people depend on.
• Ability to write production-quality frontend and own the path from design to a live experience.
• Comfort operating with ambiguity and building systems where none yet exist.
• High standards for craft, clarity, trust, and professional integrity.
• Genuine interest in using AI as leverage while remaining accountable for the work people review.
• Direct exposure to users and willingness to sit with accountants.

Responsibilities

• Own the end-to-end product experience, then write the frontend to ship it.
• Define how accountants understand what an agent is doing and why, give it context, review work, intervene, correct, approve, and undo.
• Establish the principles, interaction patterns, and visual language that make Entries distinct.
• Shape problems with accountants and clients, prototype quickly, and ship.
• Build the design system that lets a small team move fast without lowering the quality bar.
• Sit with accountants, observe real work, and turn workflow context into clear product decisions.
• Raise the bar across product, brand, web, demos, and the moments that shape how clients experience the firm.
• Sweat interaction, hierarchy, language, motion, states, edge cases, and the details others miss.
• Work with engineers so the system behind the interface is as trustworthy as the interface itself.
• Protect trust: privacy, auditability, and consequential financial decisions.

Skills

Product design

Frontend coding

Design system

User research

Tools

TypeScript

React

Job description

Toronto · Full-time · In office five days a week · $100,000–$120,000 + meaningful equity

Entries is building an AI-native accounting firm for owner-operated businesses. We are looking for a founding product designer to own the experience of working with Entries, invent the interface for agents doing real financial work, and ship those designs to production.

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 own the Entries experience: how accountants review work, how clients feel the firm, and how agents act, ask, explain, and hand work back. The design language for that world has not been settled. We do not want yesterday's SaaS patterns with a chat box added on.

You will work directly with founders, engineers, and accountants. You will talk to clients, form a point of view, and carry ideas from ambiguity to shipped product. This role involves code. Our designers do not stop at handoff. They ship their own designs to production.

This is not a conventional product-design job attached to an accounting firm. We want someone who is excited to rethink how a professional-services firm should feel when accountants, designers, and engineers work side by side.

What you will do

• Own the end-to-end product experience, then write the frontend to ship it.
• Define how accountants understand what an agent is doing and why, give it context, review work, intervene, correct, approve, and undo.
• Establish the principles, interaction patterns, and visual language that make Entries distinct.
• Shape problems with accountants and clients, prototype quickly, and ship.
• Build the design system that lets a small team move fast without lowering the quality bar.
• Sit with accountants, observe real work, and turn workflow context into clear product decisions.
• Raise the bar across product, brand, web, demos, and the moments that shape how clients experience the firm.
• Sweat interaction, hierarchy, language, motion, states, edge cases, and the details others miss.
• Work with engineers so the system behind the interface is as trustworthy as the interface itself.
• Protect trust: privacy, auditability, and consequential financial decisions.

The design experience we are looking for

You have strong hands-on product design experience shipping complex software that real people depend on. Your experience should include many of the following:

Product and interaction

• Designing dense, high-stakes workflows: review queues, exceptions, tables, documents, and multi-step work, not only marketing pages or empty states.
• Inventing interaction patterns for systems that act, not only screens that wait to be clicked.
• Turning messy operational work into a hierarchy people can scan, trust, and correct.
• Writing the interface: labels, empty states, errors, confirmations, and explanations that hold up when the work is financial.
• Establishing or extending a design system that engineers actually use.
• Sitting with users, watching the work, and changing the product because of what you saw.

Production craft

• Shipping production frontend in TypeScript, React, and a modern component system. Prototypes are useful. The job ends in production.
• Owning the path from exploration to a live experience without treating implementation as a handoff.
• Caring about states, edge cases, accessibility, and the last 10% that makes software feel finished.
• Moving between brand, product, and the moments that teach a client what Entries is.
• Working in a small team where design, product, and engineering are one loop.
• Holding a strong point of view and changing it when the evidence is better.

You do not need to have designed every kind of product. You do need strong taste, 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

• A portfolio that shows exceptional product taste and interaction craft, not just clean screens.
• The ability to write production-quality frontend and own the path from design to a live experience.
• Comfort operating with ambiguity and building systems where none yet exist.
• High standards for craft, clarity, trust, and professional integrity.
• Genuine interest in using AI as leverage while remaining accountable for the work people review.
• Direct exposure to users. You want to sit with accountants, not receive a research brief.
• 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 shipped meaningful, complex products and can explain the decisions, tradeoffs, and outcomes.
• You have designed software for operations, finance, professional services, or other consequential workflows.
• You are slightly jaded by software that adds a chat box to yesterday's patterns and calls it AI.
• You can move comfortably between a client conversation, a review screen, a design-system decision, and a pull request.
• You care about building a durable professional firm, not just assembling a portfolio of screens.
• You have a point of view on how people should work with agents, and the craft to make it feel obvious.

How we work

Designers sit next to the work

The most valuable design input is an accountant reviewing an exception or a client asking a question. We want you in those conversations, not downstream of them.

Designers ship the product

Taste without production is unfinished. Engineers build the system. Designers make the experience real, including in code.

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 person who found it and the person who can fix it.

• Base salary of $100,000–$120,000, 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 accountants, and the opportunity to shape our internal agentic operating system.
• Significant ownership over product, brand, 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.

You may like it here if

• You want your work to matter to real business owners.
• You have strong product taste and want to keep sharpening it.
• You want to help build both a professional-services firm and the technology that powers it.
• You prefer ownership to a narrow job description.
• You communicate clearly, raise issues early, and close loops quickly.
• You care deeply about the details without losing sight of the client.
• You are excited by the idea of inventing how people work with agents that do real financial work.
• You want to help invent the firm, not simply join one.

You probably will not like it here if

• You want a remote or hybrid role.
• You prefer a stable procedure to a changing system.
• You measure contribution by hours worked.
• You see implementation as an engineering handoff.
• You need every decision escalated before acting.
• You avoid sitting with the people who use what you ship.
• You treat AI as magic—or dismiss it—rather than learning how to design, use, and supervise it well.

What success looks like

Accountants can see what agents are doing and why. Review is fast without becoming a bottleneck. Clients feel a firm that is clear, responsive, and trustworthy. The design system lets a small team ship without lowering the bar. Repeated confusion becomes a better pattern.

Over time, you help Entries serve more owner-operated businesses at a higher standard without simply adding more hours or more layers of people. Your taste becomes embedded in an experience that keeps working after you move on to the next problem.